Many studies have been carried out on fragrances, flavors and perfumes worldwide. These products have important commercial value not only in India but in all over the world. Perhaps the most interesting results of the last few years in the fragrance and flavour fields are the many compounds described in this book. They may be used to engender or augment flavours in foodstuffs, chewing gums and medicinal products like mouthwash and toothpaste. The same compounds or closely related ones serve also to produce desirable aromas for perfumes, perfumed compositions such as soaps, detergents and cosmetics etc. Perfume is a mixture of fragrant essential oils and/or aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces a pleasant scent. The odoriferous compounds that make up a perfume can be manufactured synthetically or extracted from plant or animal sources. Perfumes have been known to exist in some of the earliest human civilizations either through ancient texts or from archaeological digs. Modern perfumery began in the late 19th century with the commercial synthesis of aroma compounds, which allowed for the composition of perfumes with smells previously unattainable solely from natural aromatics alone. Flavors and Fragrances (F&F) are the essential ingredients that lend taste and smell, respectively, to food and personal or home care products. Without these, all the products that we use such as toffees, chips, toothpastes, soaps and shampoos, would be tasteless or odorless, boring, functional products. Fragrances are different types; floral, fruity, woody, flower, natural, etc. and has applications in different field; soap and toiletries, cosmetics, household applications etc. Flavoring in common language denote the combined chemical sensations of taste and smell, the same terms are usually used in the fragrance and flavors industry to refer to edible chemicals and extracts that alter the flavor of food and food products through the sense of smell. Applications of flavouring are in numerous field; meat, chocolate, dairy, beverage, confectionary, bakery, teas etc. Due to the high cost or unavailability of natural flavor extracts, most commercial flavorants are nature identical, which means that they are the chemical equivalent of natural flavors but chemically synthesized rather than being extracted from the source materials. Traditionally, while flavors and fragrances were viewed as the most customized of all raw materials, and therefore commanded higher prices, in the last decade, prices have been pushed down consistently by large manufacturers.
This book basically deals with the roots and the evolution of perfumery, the part of hedonism, how perfumery is linked to the other fine arts, the art of composition, conclusion, introduction, fragrancing of functional products, line extensions, perfumery for household products, floral series : rose notes, jasmin notes, hyacinth notes, lilac and lily, orange blossom notes, tuberose notes, violet notes, mignonette, woody series: sandal notes, peppery notes, caryophyllaceous notes, introduction, aroma composition of various teas, flavory ceylon black tea, keemun black tea, green tea, pouchong tea and jasmine tea, lotus tea, soap manufacture, raw materials, shaving soap, transparent soaps, super fatted toilet soaps, the milling process, coloured soaps, perfumes, soap compounds, acacia, almond, almond soap, amber soap, buttermilk, brown windsor, carnation, chypre, cologne, cyclamen, fougere, heliotrope, hyacinth, jasmin, lavender, lilac, lily, etc.
This book contains formulae and processes of various types of flavours, fragrances and perfumes. New entrepreneurs, technocrats, research scholars can get good knowledge from this book.
1. THE ART OF PERFUMERY
The Roots and the Evolution of Perfumery , The Part of Hedonism, How Perfumery is Linked to the Other Fine Arts, The Art of Composition, Conclusion
2. PERFUMERY APPLICATIONS: FUNCTIONAL
Introduction, Fragrancing of Functional Products, Line Extensions, Perfumery For Household Products
3. ORIGIN OF NATURAL ODORANTS
Introduction, Products of Lipid and Amino-Acid Metabolism, Mono and Sesquiterpenoids, Conclusions
4. PRODUCTS OF NATURAL ORIGIN
Introduction; Concretes, Absolutes,
Floral Series :: Rose Notes, Jasmin Notes, Hyacinth Notes, Lilac and Lily, Orangeblossom Notes, Tuberose Notes, Violet Notes, Mignonette, Woody
Series: Sandal Notes, Peppery Notes, Caryophyllaceous Notes,
Rural Series: Herbaceous Notes, Green Notes, Balsamic Series:
Resinous Notes, Vanilla Notes, Fruity Series, Animal Series: Amber Notes, Maritime Notes, Musk Notes, Empyreumatic Series: Tobacco Notes
5. FLAVORING VEGETABLE PROTEIN MEAT
Development of Characteristic Meat Flavors, Properties of Meat Analogs as Compared to Meat, Application of Meat Flavors in Meat Analogs
6. FLAVOR ASPECTS OF CHOCOLATE
7. THE AROMA OF VARIOUS TEAS
Introduction, Aroma Composition of Various Teas, Flavory Ceylon Black Tea, Keemun Black Tea, Green Tea, Pouchong Tea and Jasmine Tea,
8. WINE FLAVOR
Introduction, The Taste of Wine, Wine Aroma, Oak Barrel Storage and Wine Flavor, Influence of Spoilage
9. MEAT FLAVORINGS
Sulfur-containing Compounds, From Yeast, From Animal Products, Meat-Flavored Shortening for Deep-Fat Frying, Other Compounds, Enhancing Meat Flavors
10. FRAGRANCESâ€“FLORAL AND FRUITY
Floral, Octadienes, Hexyloxyacetonitrile, Cyclopenta-none Derivatives, 2-Ethyl-6,6-Dimethyl-2-Cyclohexene-1-Carboxylic Acid Ethyl Ester, a-Oxy(Oxo) Sulfides, Aliphatic Dibasic Acid Diesters, 3-(10-Undeceny-
loxy) Propionitrile, Tricyclodecane-Methylol and
Derivatives, 2-Methyl-2-Alkyl-Alkanoic Acid Esters, Trimethylcyclohexylethyl Ethers, Cyanoethylidene-Bicyclo-Heptenes, Certain Crotonyl-Trimethy-lcyclo-hexanes, Ketone Acetals, Certain Allyl Ethers, Nonanols, Nonenols and Their Monocarboxylic Acid Esters, Fruity Fragrances , a-Oxy (Oxo) Mercaptans, cis-Oct-6-en-1-al, Safranic Acid Esters, Maltyl-2-Methyl Alkenoates
Woody-General, Vetiver, Sandal, Cedarwood
Introduction, Perfume Oil Formula, Manufacture of Perfume Oils, Control by Bar Code, Machinery
and Apparatus, Storage of Fragrances and
Perfume Oils, Safety Aspects, Future Prospects of Compounding
13. SOPHISTICATED OR FANTASY PERFUMES
Introductory, Floral Bouquet Perfumes, Aldehydig Perfumes, Chypre Types, Oriental Perfumes, Green Perfumes, Dominant Note Types
14. FLOWER PERFUMES
Rose, Jasmin, Orangeflower and Neroli , Violet, Acacia, Broom, Carnation, Cyclamen, Fougere (Fern), Gardenia, Hawthorn, Heliotrope, Honeysuckle, Hyacinth, Iris, Lilac, Lily-of-the
Valley, Linden (Lime Blossom), Magnolia,Mignonette (Reseda), Mimosa, Narcissus, Nardo, New-Mown Hay, Nicotiana, Opopanax, Orchid (Orchidee), Pansy, Peony, Phlox, Stocks, Sweet Pea, Syringa (Philadelphus), Trefle (Clover), Tuber Rose, Verbena, Wallflower, Wistaria, Ylang-Ylang
Propellents, Containers, Valves and Actuators, Filling and Testing
16. THE PRODUCTION OF NATURAL PERFUMES
17. MISCELLANEOUS FANCY PERFUMES
Non-Alcoholic Concentrates, Abronia, Amber, Synthetic, Ambre Royale Aux Fleurs, Ambrosia, Benzoinette, Boronia, Bouquet Des Alpes, Bouvardia, Cananga, Coronilla, Corylopsis, Decumaria, Dillenia, Erica, Fagonia, Glycine, (Wistaria), Hancornia, Hugonia, Idealia, Ismene, Jonesia, Kleinhovia, Laelia, Lime Blossom, Monimia, Nemesia, Night Scented Stock, Opoponax, Passiflora, Pavetta, Randia, Santolina, Stephanotis, Syringa, Tinnea, Well-Known Recipes, A la Mode, Bouquet Des Fleurs, Bouquet dâ€™Esterhazy, Buckingham Flowers, Essence Bouquet, Eau de Berlin, Frangipanni, Horse-Guardâ€™s Bouquet, Hovenia, Japanese Bouquet, Jockey Club, Kiss Me Quick, Leap-Year Bouquet, Bouquet A la Marechale, Millefleur Bouquet, Musk, Mousseline, Polyanthus, Rondeletia, Tulip, Yacht Club, Continental Practice, Chypre, Lilac
18. MONOGRAPHS ON FLOWER PERFUMES
Acacia, Carnation, Cassie, Chypre, Cyclamen, Fern, Gardenia, Hawthorn, Heliotrope, Honeysuckle, Hyacinth, Jasmine,Lilac, Lily, Magnolia, Mimosa, Narcissus, New-Mown Hay, Orange Blossom, Orchids, Reseda, Rose, Sweet Pea, Trefle, Tuberose, Violet, Wallflower
19. TOILET WATERS
Honey Water, Aqua Mellis, Hungary Water, Eau de Cologne, Modern Prototypes, Amber Cologne, Quickly Matured Colognes, Flower Modifications, Mimosa Cologne, Trefle Cologne, Terpeneless Oils, Cheap Colognes, â€˜Frozenâ€™ Eau de Cologne, Lavender Water, Quickly Matured Lavenders, Amber Lavenders, Florida Water
20. SOAP PERFUMERY
Soap Manufacture, Raw Materials, Shaving Soap, Transparent Soaps, Super-Fatted Toilet Soaps, The Milling Process, Coloured Soaps, Perfumes, Soap Compounds, Acacia, Almond, Almond Soap, Amber Soap, Buttermilk, Brown Windsor, Carnation, Chypre, Cologne, Cyclamen, Fougere, Heliotrope, Hyacinth, Jasmin, Lavender, Lilac, Lily, Narcissus, Opoponax, Rose, Santal, Sweet Pea, Verbena, Violet, Antiseptic and Medicated Soaps
21. BEVERAGE FLAVOURINGS AND THEIR
Introduction, Categories of Beverages, Types of Flavourings for Beverages, Methods of Extraction, Solubilisation and Concentration of Flavourings, Beverages Based on Ginger, Formulation of Beverages
22. THE FLAVOURING OF CONFECTIONERY
Introduction, Basic Confectionery Types, Recipes, Inherent Flavours, Flavours From Ingredients, Flavours Developed During Processing, Selection of Flavourings
23. FLAVOURINGS FOR BAKERY AND GENERAL
Ingredients, Flour, Sugars, Fats, Liquids, Gases, Other (Minor) Ingredients, Bakery Products,
Bread, Hot Plate Goods, Morning Goods, Powder
Goods, Biscuits, Cakes, Baking Process, Bakery Fillings, Jams and Jellies, Marshmallow, Creams,
Biscuit Creams, Icings, Summary of Flavouring Characteristics
24. DAIRY FLAVOURINGS
Introduction, Milk and Cream, Yogurt and Fermented Products, Butter, Cheese,
Manufacturing Considerations, Conclusion
25. FRUIT AND VEGETABLE FLAVORS
Fruit Flavors, Vegetable Flavors, Fruity Flavor Enhancers, Fruit Bits
Art of Perfumery
THE ROOTS AND THE EVOLUTION OF PERFUMERY
history attributes the
first perfume container to the period of Darius III (4th century bc)
of perfumery reach much deeper into the past.
first human beings had to rely on their sense of smell to survive
to recognize the various scents nature provided: animals of course but
plants flowers trees fruits grains roots and resins. Their awareness of
olfactory abilities had awakened.
odours have a tremendous influence on flavour people applied their
abilities to the preparation of meals to perfume their food even before
term had been created to communicate such impressions.
spices and herbs whose properties they eventually discovered just like
grains fruits and bark rapidly extended their olfactory know how. To
their diet they extracted oil from oleogenous grains and fate perhaps
hand they macerated vegetable and herbaceous ingredients into it. These
gave their properties and odours to the oil. It is safe to say that the
rose oil probably dates back somewhat further than we might expect.
not being dissociated from pleasure nutritional or therapeutic values
easy to move to adornment perhaps even before the idea of religious
was born because feminine seduction no doubt goes back to Eve. The
representatives of Homo sapiens were so observant and sensorially awake
necessity that they probably benefited and took pleasure from
derived from these fragrant materials.
he even knew how to make fire man had already learned from natural
heat transformed the odour and flavour of vegetables and flesh. After
of making fire was discovered initial applications were no doubt of a
nature. However the fragrant smoke of burning herbs rising to the sky
only trigger the spirit of those first religious practitioners . . .
How not to
associate smoke and odour? Per fumar perfumer would one day become the
fire and all the progress it engendered pottery among other skills led
construction of the first distillation equipment. The remains of one
found in Mesopotamia and are said to be 5000 years old. In other words
Arabs actually did little more than rediscover the alembic.
in metaphysics in Syria and Egypt as well as for religious purposes in
and fragrances except for a few historical setbacks would become
Having discovered the antiseptic values of fragrant balms and resins
Egyptians embalmed their most famous dead the pharaohs.
the Middle and Far East the first application of fragrances in daily
the form of beauty products rather than perfumes. Ointments creams and
preceded the use of odorants simply for their fragrance.
to perfumed oils and later to alcohol a good extraction solvent and a
vehicle for the first perfume mixtures the era of smelling good had
perfumery as it is known today was still far away.
fact for several centuries olfactory practices were limited to simple
recipes. The 18th and 19th centuries were years of excess of terror and
conquering wars followed by the pretentious and ridiculous refinements
Muscadins. Only the end of the 19th century saw the birth of real
result of an evolving industry: the production of odorous substances by
chemical reactions. These odorous compounds added to the old recipes
them by setting new fragrant accents often strong and long lasting
unprecedented combinations. Later it would be discovered that some of
fragrant components were actually hidden in highly complex natural
from which they could not always be extracted individually. Now
isolated form they offer completely different possibilities than when
in a natural substrate such as an essential oil or an absolute.
growing list of chemically defined odorous substances allowed man to
simple recipes and to create real formulae which gave way to original
forms invented by formulators.
formulators had worked with odorous materials of natural or synthetic
much in the same way that musicians work with tones or painters with
They had combined specific properties of their materials to create a
new form and not a mere addition to existing forms. With their material
had composed the olfactory composition. This stage represents the
perfumery as it is known today it has existed for just one century.
course perfumery passed through various stages during the past 100
craftsmanship industrialization and commercialization. It had to
evolve under tho diverse forces of a changing world. These factors need
mentioned here in order to understand better the current situation in
perfumery therefore was born at the very end of the 19th century the
combining for the first time both natural raw materials and synthetic
chemicals. I will only cite the most famous the still very much alive
in 1889 whose incredible centennial was smothered by the clamours of a
bicentennial. What a pity!
real champion the mastermind of this contemporary olfactory
Francois Coty also gifted in marketing and sales helped perfumery leave
first stage of rough sketches to enter the world of fine arts. He
revolutionized not only compositions but also bottles packaging and
methods. He was the first and probably the only real professional in
and Chypre were the glorious masterpieces which Coty revealed to his
contemporaries. And Muguet des Bois introduced in 1936 two years after
death but unmistakably one of his creations was the most beautiful
evocation ever cultivated on this theme at a time when resources were
by his example his peers eventually surpassed each other each through
ingenuity each faithful to his own taste. Guerlain Houbigant (Parquet
and Caron (Ernest Daltroff) became renowned for their creations. In
these perfume houses the owners were tasteful and perceptive composers
complete initiative and responsibility from concept to sale. Success
sanction of united action. Unfortunately these qualities were not
and the future of these houses would suffer the consequences.
World War I having seen the success of perfumers renowned fashion
wanted to exploit this success to stabilize precarious fashion
first Coco Chanel following the failure of Poiret was exceptionally
to stumble upon Ernest Beaux who had worked for the Rallet Perfumery in
before 1914 and had subsequently moved to La Bocca Cannes France in
had created a perfume for Rallet which under the label of Rallet no. 1
a failure. Rallet offered it to Coco Chanel and was her supplier during
initial years. Its launching in 1922 or 1923 as No. 5 by Coco Chanel (a
in this field and with limited resources) was far from spectacular. The
introduction was made by the powerful Wertheimer Group (Parfums
took over the activities of Parfums Chanel. Beaux finally a member of
Chanel group would be the author of several other masterpieces.
designer Jeanne Lanvin also tried her luck with a modest perfume My Sin
1925. She as well would meet a great perfumer who would conjure the
spectacular tetralogy in the history of perfumery: Arpege Scandal
Marcel Rochas and Christian Dior followed the footsteps of their two
and also tasted the sweetness of success. In these four cases when the
was no longer pulling all the strings the composition of the perfumes
ensured by true professionals and their distribution was controlled
the fashion designers or by professionals like Bourjois. The break with
tradition was therefore limited and all artistic objectives were
the diversity of new brands introduced by amateurs not familiar with
nuances in perfumery and financed by groups who did not respect the
true perfumery triggered dramatic changes. Perfume was no longer a
work of art. It had been reduced to a commercial product sold under the
lucrative of conditions. Its production was given to the highest bidder
setting any aesthetic priorities marketing being the choice method to
on the public. The entire system was based on this principle putting a
the creative wave of parfums a risque as they were called by the new
charge. However the real risk lies in launching any old product it is
fact that nine launches out of ten are a failure.
perfumery is uprooted. Only a revolution can redeem it.
THE PART OF HEDONISM
is attributed to the School of Cyrene which was established by
(around 435 350 bc) a contemporary of Plato and a follower of Socrates.
School was continued by his daughter Arete and his grandson Aristippe
known as the Metrodidacte who because of his contacts with the
their cynicism may very well have systematized his grandfathers
philosophical doctrine which aimed for an ethic was founded on the
immediate impressions. It advocated the search for pleasure while
and preferred intensity to quality. Pleasure was always something good
its origin engendered shame.
philosophy of (immediate) pleasure is the negation of all arduous
in sports or the arts of any intellectual effort of any creative
any devotion implying sacrifice or of any generous altruism.
who would place perfume under the sign of hedonism would arbitrarily
to sensual and possibly vulgar aspects completely neglecting the
aesthetic quality which has essentially characterized the great
perfumes of the
most hedonism translates into pleasant sensations. In terms of
sensations a distinction must be made between the perception of the
the perfumer and even of the experienced amateur. The fact that to
mortals some odours are considered pleasant and others unpleasant can
attributed to a lack of education and to an innate taste which impedes
layman from making an objective and technical judgement on the value
of odours. However after a short but inevitable emotional reaction the
motivated and experienced perfumer no longer distingui shes between
and unpleasant smells. This is like the music composer who considers
be elementary forms which can be combined into intricate music. The
longer judges the notes but the rapport he has created between them.
applies to perfumers. This is one reason why 1 studied Kant who so
distinguished between things pleasant and things aesthetic.
perfumer judges odours in terms of quality intensity and duration of
perceptibility. The latter must be distinguished from intensity even
duration is defined as intensity in time. Volatility is the fourth
component which plays a considerable role in the genesis of a
without volatility there would be no perfume. I have stated the above
convention because these attributes arise not from odours (pheno menon
conscious ness) but from the stimulus which determines them or more
the reaction between the odorous molecule and the receptive
which it will bind. This reaction triggers a change of the normal
the living cells which translates into electric impulses a set of waves
are decoded by the brain. The consciousness of odours is born.
has been an on going
pursuit of mankind for centuries. The earliest mention of soap for
purposes appeared in the second century ad. A great deal has happened
then as the human race became quite serious about getting and remaining
This seriousness is probably the genesis of the age old adage
next to Godliness.
until the early part of this century was there anything but soap
cleaning one s body or the clothes on it and it was a rather crude soap
that. As the years progressed however a variety of cleaning products
appearing for a yet unsophisticated and undemanding consumer.
evolution began with a small selection of washing products for personal
well as clothes in the 1920s and 1930s. These early products were
allowed the soap base odor to linger on the skin and cloth. By the
perfumes started to make their way into functional products. These
the most part relied on citronella thyme and iemongrass oils along with
isolates and chemicals such as bornyl acetate camphor diphenyl oxide
it appeared that the perfumery development of functional products was
for fast growth. World War 11 stunted the growth of this industry as it did others as it caused monumental
shortages of raw
materials. It was not until the 1950s therefore that the business got
industry was up and running. The 1950s brought us expanded palettes of
materials through the production of greater numbers of synthetic
called aromatic chemicals which later became known simply as aroma
The fragrance industry expanded to meet the growing need of cleaning
manufacturers who were now creating new products at a quickened pace.
new products were aimed at the consumers so they could keep their
environments their wearing apparel and themselves clean.
the fun began because along with this unprecedented growth came a
new segment of the industry creative perfumery for household products.
Perfumers were not only required to become more and more imaginative
also faced with the challenge of mastering and manipulating raw
through hostile base environments.
FRAGRANCING OF FUNCTIONAL PRODUCTS
the mid 1970s the fragrancing of functional products became a very
part of the industry contributing significantly to the growth and
fragrance suppliers ultimately losing their stepchild image to the fine
that same decade we witnessed the larger fragrance supply houses
creative departments of perfumers whose sole responsibility was to work
functional products area. Suppliers with research capabilities to
aroma chemicals were feeding the creative efforts of the perfumery.
and tedious stability studies of fragrance raw materials produced
often gave direction to the research laboratory efforts to find new
chemicals which answered specific stability and creative needs.
the close of the 1970s the work emanating from the research facilities
household products manufacturers produced aggressive bases which were
with problems that the household products perfumer had to face problems
carried into the next decade. Examples included solubilities active
and chlorine bleaches encapsulated chlorine fabric conditioners enzyme
and so on.
if this were not enough the perfumer had then to consider linear
diffusion and longevity for perfuming the environmental air fresheners
emphasis on continuous action. These various mechanisms created
related more to the physical aspects of the chemistry of fragrance
than to the interaction of a product s base nature with the fragrance
household products perfumers needed to address all of these various
for their fragrance creations often learning something from one product
and applying it to another. At all times the tenets adhered to with
project were raw material stability availability and cost and the
these three to produce a fragrance which would aesthetically send the
appropriate signal about the product to the consumer.
specific problems encountered by the perfumer when presented with the
of fragrancing functional products a category which can be further
into cosmetic and household products.
all great fragrance ideas for functional products are born
independently in the
mind of the perfumer. Rather they are inspired by what has gone before
is currently in the marketplace in an upscale way. Fine fragrances have
recent years been a source of ideas which inspire the creation of a
product perfume. This process is known as the trickle down effect.
tried and true method of developing new functional products perfumes it
several obstacles that must be overcome before a successful transfer of
fragrance theme to a functional product can be accomplished.
fine fragrances can create a polarizing effect among consumers causing
love/hate feeling toward the fragrance. Functional products on the
other hand particularly
the household ones cannot afford this love/hate reaction from consumers
they must be acceptable to a broad cross section within the consumer
Therefore the unique combinations which give birth to the couturier
theme have to be modified tamed and massaged by the functional perfumer
broaden the fragrance profile for greater consumer acceptance. Of
are always exceptions to this successful translation of polarizing
to those which trickle down almost exactly intact giving consideration
to cost stability
more recent introduction by Dior Poison has already made its way into a
air freshener and prognosticators see this as on the way for fabric
extensions of couturier fragrances into functional cosmetics is the
the most obvious example of the trickle down effect although not
in the truest sense of this phenomenon. Today it is expected that the
fragrance note in the perfume or cologne will be carried throughout all
products in the line of the same name. Trickle down in the present
from couturier perfume to hair spray deodorants bar soaps detergents
softeners etc. In attempting to adapt a fragrance theme for functional
perfumers must consider the following factors.
of couturier theme in product category.
considerations of matching diffusion stability of both odor and color
paramount importance. Substitution of raw materials is almost always
availability of aroma chemicals and natural materials.
fragrance materials to comply with the IFRA and RIFM safety guidelines.
chemicals create the palette for today s modern perfumer that makes it
to translate couturier perfumes into other products. Cologne (notes)
stability and musk notes do not discolor these are just two examples of
aroma chemical developments in the last 30 years have become the key to
expanding world of fragranced products.
products such as shampoos and hair sprays have provided fertile areas
trickle down effect. The desired residual character of the couturier
is easily translated to these products. Popular types in shampoos are
from fragrances like Chloé Chanel No. 5 Charlie and Lauren. Major hair
products utilize the fragrance types of Anais Anais L Air du Temps and
of the top beauty complexion soap bars in the world have been inspired
Arpége Chanel No. 5 Chamade and Cabochard.
products and cleansing products in general place too many constraints
perfumer trying to translate a couturier fragrance for the end use.
base odor indicative of the active ingredient and pH considerations
direction of fragrances in the products. This however does not preclude
perfumer from being inspired by a couturier theme and using it as a
point modifying the theme until all constraints are dealt with
usually producing a fragrance which bears slight resemblance to the
this does not dissuade the perfumer from saying the creation is of a
couturier type taking into consideration all the aforementioned reasons
changes in the odor profile.
the natural order of things there are also two variations of the
theory: those that trickle up and trickle across. An example of the up
is the Youth Dew bath oil by Estee Lauder which became the inspiration
perfume oil. Another example of bath oil to perfume is Dioressence by
Though these examples are rare they do happen giving credence to the
state of creativity and inspiration.
across has one famous example the Johnson & Johnson Baby Powder
powdery rose accord which
overshadows all others and probably has become the most overdone
of the past three decades. This fragrance implies on the very first
softness and babies. All perfumers even those with moderate experience
difficult if not impossible it is to change the mind set of marketers
product formulation chemists away from the J&J type when
fragrancing baby products bathroom deodorants or any other product
demand a powdery fragrance type. The marketing request is usually for
new and different but which smells like J & J Baby Powder.
There is a fear
of limited product acceptance by the consumer if it does not have
notes which can always be related back to the Baby Powder note.
popularity of J&J Baby Powder fragrance making it one of the
classic blends has been said to be responsible for Ombre Rose Baby Soft
Sweet Honesty all perfume/cologne fragrances which are examples of the
notes did not always enjoy the prestige of being the lead notes of many
couturier fragrances as found in today s markets. Rather these notes
complete fragrances themselves used particularly in the USA as strong
agents and most effective in public lavatories. These fragrances which
on flavors with their intensity were discharged into the atmosphere
mechanical means or continuous action para blocks.
was only in the late 1960s and early 1970s that fruity fragrances began
respectability in their own right by providing a whole new range of
concepts for functional products. Shampoos by the dozens had myriad
notes espousing their different claims on the hair.
fruity era trickled across to many different product areas. The natural
fragrances picked up along the same lines giving way to vegetable and
food like fragrances.
fruity notes have trickled up to modify and lead the couturier palettes
aldehydic florals chypre spicy woody etc.
fruity notes have also trickled down to detergents and fabric softeners
their imprint of residual quality along with richness and masking power.
the trickle down phenomenon is occurring more quickly than it did in
The sophisticated demands of the customer for more upscale fragrances
functional products area along with the availability of a greater range
aroma chemicals yielding increased stability and creativity in more
bases have made this possible. As mentioned. Poison has already been
to a room freshener.
functional products perfumer has much to be inspired by to enhance his
creativity but he needs the knowledge and experience to make successful
first group of functional products to be considered is line extensions
perfume/cologne. While these do present problems they are not as severe
seemingly insurmountable as those in the household products area.
stability and color are the prime considerations when making line
Costs ot extensions are proportionately less than the cologne oil. Some
guidelines are as follows: the bath fragrance might be 60 75% of the
the cologne the talc hair products baby lotions and deodorants at 50%
cologne with the soap interpretations coming in the 30 40% of the
as a fact finding experiment the cologne oil should be incorporated
bases at appropriate levels while the perfumer using his experience
the formula for obvious necessary modifications for cost and
first exercise involving the cologne oil will help to narrow down the
problems such as coloration and discoloration. Frequently one lower
version may work in two or three line extensions. Therefore fragrances
developed from modified cologne oils for line extensions are usually
intense and used at higher levels than those in non line extension
products. Fragrances which are lower cost versions of cologne oil and
work in more than one line extension may tolerate the use of solvents
costs where necessary.
of Natural Odorants
substances that have a molecular weight below about 400 and an
vapor pressure at room temperature can be perceived as having odor. The
spectrum of odorants is thus limited to relatively small neutral
compounds including undissociated acids and nitrogenous bases.
organic acids are sufficiently volatile to contribute to natural
(vinegary) propionic (goaty) butyric (spoiled butter) and lactic
acids are odorous at relatively high concentration.
aroma research was largely directed toward the isolation identification
cataloging of specific odor producing constituents from the complex
produced by nature. This work continues and many important aromas from
foodstuffs beverages smoking materials and flowers have only recently
and the constituents positively identified. The cost of natural
to the often difficult separation of the desirable component(s) has
the development of chemical syntheses of many substances from more
materials including petrochemical feedstocks. Synthetically derived
in many cases have superseded those produced oy living organisms.
more recent emphasis on natural as opposed to artificial ingredients
refocused attention on the origin of natural odorants and on the
improving biological methods for the production of these materials.
advances in analytical techniques and instrumentation the use of
tracers the development of instructive biomimetic syntheses and
reactions and the exploitation of cell free enzyme systems have greatly
facilitated our understanding of the origin of natural odorants via the
enzymatic and occasionally non enzymatic processes that occur in
and plant cells. Of the natural fragrances those of plant origin are
the most structurally diverse. In spite of this diversity and the
biogenetic possibilities most odor bearing compounds appear to be
formed by way
of relatively few often overlapping metabolic pathways that form the
PRODUCTS OF LIPID AND AMINO ACID METABOLISM
aldehydes ketones lactones and related compounds are among the most
distributed of natural odorants and are often major contributors to
aromas. Many such compounds associated for example with the essence of
and pear are neither produced during growth nor present at harvest.
arise during a short ripening period marked by a climacteric rise in
respiration and the onset of cellular catabolic processes. The
biogenesis of a
large number of these volatile aliphatic types can be rationalized by
a reasonably small number of metabolic pathways in which non volatile
acids and amino acids serve as the most important precursors.
bearing aliphatic compounds are considered to be produced via three
pathways: (1) Lipoxygenase catalyzed conversion of polyunsaturated
into C6 and C9 aldehydes and related substances and into C12 and C9 oxo
conversion of fatty acids via a and b oxidation into short chain acids
and ketones and related metabolites (3) conversion of amino acids to
corresponding Cn 1 acyl derivatives via trans amination and oxidative
major fatty acids of plant glyceryl lipids are the even numbered
derivatives from C12 to C18 and the unsaturated C18 derivatives (oleic
and linolenic acids) all of which are products of primary metabolism
the well known acetyl coenzyme A malonyl coenzyme A pathway. Free fatty
exist at very low levels in intact plant cells and must first be
the corresponding glycerides and phosphoglycerides by enzymatic
(i.e. by the action of lipases and phospho lipases). Unsaturated fatty
(primarily linoleic and linolenic) may then become substrates for
enzymatic oxygen insertion reaction ultimately leading to the formation
of C9 and
C13 hydroperoxides. The lipoxygenase reaction mimics radical initiated
autoxidation however the enzymatic process is both regio and stereo
selectivity depending on the enzyme source. Hydroperoxide lyases then
these reactive compounds the cleavage of the C9 hydroperoxide leading
unsaturated C9 aldehydes and 9 oxononanoic acid and the cleavage of the
hydroperoxide leading to C6 aldehydes and the corresponding 12
acid. Lyase activity has been demonstrated in a variety of plants
cucumber tomato pear and apple. The lyase from pear fruit is specific
C9 hydroperoxide whereas that from tomato fruit is specific for the C13
hydroperoxide. The lyase from cucumber fruit accepts both isomers.
and trans 2 nonenal originate from linoleic acid (C18:2) as illustrated
1 while trans 2 hexenal and nonadienal arise from linolenic acid
Alcohols are derived from these aldehydes by the action of alcohol
dehydrogenase(s). The C6 aldehydes and alcohols are largely responsible
characteristic odor of green leaves and they contribute to the aroma of
variety of fruits. The 3 enals are converted by an isomerasc to the
2 enals. Such isomerization of (3Z) hexenal to (2E) hexenal yields leaf
aldehyde . The former provides leaf alcohol upon reduction. Nonenal and
nonadienal and their derived alcohols have been described as melon
violet like. Species dependent variations in the type and quantity of
fatty acids and the specificity of lipoxygenases lyases isomerases and
dehydrogenases are responsible for the diverse mixtures of C6 and C9
encountered in plant volatilcs.
alternative means of generating volatile chain shortened products from
fatty acids of fruits and vegetables is the b oxidation pathway. This
scheme is initiated by conversion of the fatty acid to the
coenzyme A derivative by the action of acyl thiol ligases (acyl Co A
acyl thiokinase). The acyl chain then undergoes sequential desaturation
C3 hydration of the double bond to the C3 (b) hydroxy derivative and
to the corresponding C3 (b) ketoacyl chain. In the final step of this
enzyme thiolase with the assistance of coenzyme A cleaves the b keto
to yield acetyl coenzyme A and the acyl coenzyme A with the chain now
by two carbons. Repetition of the b oxidation cycle would ultimately
chain to acetate units. Both saturated and unsaturated chains may be
by this route although in the latter case the participation of
reduction and/or isomerization step(s) is required to convert
chains to normal b oxidation intermediates. The resulting chain
acyl coenzyme A esters may be reduced to the corresponding aldehydes by
action of acyl coenzyme A reductases and the aldehydes in turn
alcohols by dehydrogenases. The alcohols thus formed may be esterified
acyl coenzyme A derivatives by the action of transacylase. A
for these transformations is provided in Fig. 2 in which the production
compounds as ethyl octanoate and octyl acetate is illustrative of the
set of volatile metabolites which could be so generated.
chain products are formed from the more common even chain fatty acids
process of a oxidation in which flavin dependent enzymes decarboxylate
fatty acid via the a hydroperoxy intermediate to yield the aldehyde
by one carbon. Reduction of the aldehyde may occur and the resulting
may enter the esterification cycle as illustrated. Alternatively
the aldehyde to the acid could lead to the production of odd chain
propionates and valerates.68 It is obvious that the combination of a
oxidation when coupled to reduction and esterification steps is capable
generating an extremely wide and complex range of volatile odor bearing
Oxidation and alternate modes of lipid oxygenation are also thought to
involved in the production of additional odorants in plants including
methyl ketones and lactones.
Pathway for the biosynthesis of short chain aldehydes alcohols and
methyl ketones are characteristic of the essential oil of rue (Ruta
graveolens). Most prominent are 2 nonanone and 2 undecanone (and the
corresponding secondary alcohols) which are considered to arise from
C12 acyl chains in the course of b oxidation. Thus following conversion
b ketoacyl chain decarboxylation yields the odd chain methyl ketohe.
The g and
d lactones characteristic of pineapple peach apricot strawberry mango
coconut undoubtedly arise from intermediates of fatty acid b oxidation
biosynthetic elongation process. It seems likely that C4 unsaturated
undergo hydration of the double bond or epoxidation and reduction to
C4 and C5 hydroxyacyl chains which are subsequently lactonized to the
corresponding g and d lactone. Macrocyclic lactones such as those found
galbanum angelica root and ambretre seed are probably formed by w (or w
hydroxylation of the corresponding odd or even acyl chain followed by
esterification via a transacylase type enzyme. The aroma producing
(bicyclic g lactones bearing a fused cyclohexane ring) typical of the
oils of certain Umbelliferae are probably formed by the polyketide
rather than by oxidative modification of normal fatty acids.
branched chain aldehydes alcohols and esters are also important aroma
of ripening fruits and vegetables produced during the climacteric rise
respiration. Such branched chain derivatives arise from branched amino
transamination and oxidative decarboxylation to the shortened acyl
derivative. Cellular levels of free leucine and valine may increase
fold during the climacteric period and may serve as precursors of 3
and 2 methylpropyl derivatives respectively. The aroma of field ripened
tomatoes is attributed to esters of 3 methyl 1 butanol derived
leucine. Thus leucine amino transferase converts the amino acid to the
acid (a ketoisocaproic acid) which is decarboxylated to 3
The coenzyme A ester may either be a substrate for transacylation or be
to the corresponding aldehyde and alcohol (isoamyl alcohol). Valine and
isoleucine may be transformed to branched esters aldehydes and alcohols
same general pathway and alanine and aspartic acid are similarly
was discovered as a principal aroma constituent of jasmine in 1899.
cyclopentenone derivative has a fruity celery like odor which upon
sweet floral and blends well with all floral scents. Of the numerous
in jasmine flower oil Jasmone methyl jasmonate and jasmine lactone are
to carry the principal jasmine fragrance while comprising but a very
fraction of the fresh weight of the flowers.
proposed biosynthetic schemes for the formation of jasmonoid compounds
with polyunsaturated fatty acids. The extensive studies by Vick
have led to a proposal for the formation of jasmonic acid which serves
plant growth regulator (promotes senescence). This pathway begins with
hydroperoxide derivative of linolenic acid (via lipoxy genase see
is dehydrated (via hydroperoxide dehydrase of the chtoroplast) to a
allene oxide. The latter may undergo hydrolysis to ketols or
rearrangement and cyclization to 12 oxo 10 15 phytodienoic acid a key
intermediate of the pathway which by reduction of the endocyclic double
and b oxidative carboxyl end shortening yields jasmonic acid
this product presumably by S adenosylmethionine could provide methyl
of Natural Origin
INTRODUCTION CONCRETES, ABSOLUTES
diversity of the natural products used in perfumery is very
remote antiquity until the end of the nineteenth century i.e. 1880 90
perfumery industry had used only natural products for its perfumes. The
development of organic chemistry by French and German scientists
important dye industry and then the synthetic odorants industry these
industries had many points of contact.
in synthetic chemistry had major repercussions on perfumery and marked
beginning of a new epoch. The enthusiasm resulting from obtaining
similar to those of certain flowers led at one time to the belief that
synthetic products could entirely take the place of natural products.
perfumers took this view but those of the French school were always
observe and retain in perfumes a balance between the relative
natural and synthetic products. This resulted for a long time in the
superiority of French perfumes to the others quite apart from the
the artistic aspect of the Paris atmosphere and of French art in
Grasse natural essential oil industry exerted a far reaching influence
years went by and successes with artificial perfumes which indeed
proportion of natural products such as Chuit s Dianthine brought the
into fashion again.
later on prompted Hubert Fraysse who presides over the destinies of
say: It is now possible to dispense almost entirely with natural
is undeniable that the methods of analysing essential oils had
considerable development with the introduction of spectrography mass
spectrography gas chromatography etc.
Stoll commented in 1962 upon the complexity of the composition of a
essential oil and taking by way of example an absolute oil of jasmin
been very fully analysed he reported that 14 different alcohols had
identified in a large portion of that absolute oil and in a far smaller
by weight 28 to 29 alcohols had been found which it was not possible to
identify. The lecturer added: No chemist in the world would tackle such
those who know as a true perfumer does the influence of tiny quantities
certain products in a composition it will be realised that it is very
to replace in a high grade perfume a natural product by an artificial
Perfumers know moreover that lavender is greatly improved by a trace of
phenylethyl alcohol. A trace of tincture of ambergris improves
The merest suggestion of a certain lactone often improves a lily of the
And so on. The consequences of this extreme complexity of natural
materials may be summarised as follows:
practically impossible to produce a perfect reconstitution of a natural
essential oil by means of synthetics. (Many reconstitutions are
used for part or even total replacement of excessively expensive
products. Such reconstituted or artificial oils are economically
tend to improve in quality as time goes on and research expands. They
purchased as such as is often the case or in some cases are made by the
which exists in natural essential oils can only be obtained in
provided that very many component substances are used especially in the
of olfactory analogues. This runs counter to the theory which claims
perfume must consist of a small number of components: unless of course
endeavours to produce more or less diagrammatic perfumes.
what this analysis of natural products teaches us the fact cannot be
that the latter have various other properties that are favourable to
in perfume compositions. Thus they produce homogeneity round off the
the harshness of synthetics etc.
persistence may be imparted to perfumes containing naturals but much
course on the quantity used as well as the type.
essential oils and those obtained by expression from the peel of citrus
etc. all possess terpenes to a greater or lesser degree and these play
important part in perfumes by exercising an exalting effect. In the
language of the perfumer: ils poussent le parfum (they push or boost
is true that deterpenated or terpeneless essential oils are also
because they can be employed in larger quantities in alcoholic solution.
very important requirement for natural products is quality. How is it
ensured? There is of course the physical and chemical standards for
them but these are only an indication the final decision remaining with
is it possible to know the olfactory quality for each of the natural
oils? Although the faculty of judging olfactory purity and quality may
extent be inherent it is one that must be adequately trained and
it depends above all upon a well stored reliable and discriminatory
consider elsewhere the actual training of the perfumer but here may be
just a few points which have to be taken into consideration when
natural perfumery raw materials:
The custom more or less permissible of
making mixtures which physical and chemical analysis may or may not
which olfactory analysis can readily detect.
For a determined natural product olfactory
analysis recognizes the origin of the product. For instance a Grasse
distinct from an Italian jasmin or the jasmin of one supplier from that
and preferences of a perfumer play a part here. Thus one perfumer will
a jasmin for the fresh part the sharp top note while another will seek
the warm rather jam like and sometimes indoloid note.
a young perfumer who wishes to know the raw materials olfactorily must
available for his education the largest possible number of products.
have touched on the problem of the adulteration of natural products and
to be admitted that sometimes certain inexperienced buyers make trouble
themselves. What is a seller to do who offers a true natural jasmin
which the incompetent buyer refuses to place a large order saying that
jasmin is 25 per cent too expensive and that he has had offers at the
price? The seller will almost certainly submit a fresh sample which
will be 30
per cent cheaper and has been arranged accordingly. This happens more
than might be imagined.
examples would suggest that the purchase of odorants should be made by
experienced perfumer or perfumery buyer. All too often the general
of a perfumery concern tends nowadays to make the buying department for
perfumery raw materials independent of the technological side doubtless
order to avoid any understanding if one may use the phrase developing
buyer and seller. It is doubtful however whether the gains made by this
division of power outweigh the losses. Buying usually suffers when left
relatively unskilled: there is a loss of immediacy opportunity and
perfumer moreover is deprived of vital contact with an important source
information if someone else in the firm and not he habitually
sellers representatives for it is they who are in touch with the
world of all his competitors. It should never be forgotten that the
bears responsibility for the creation of the perfume and the continuity
quality and he ought therefore to live in the full atmosphere of
fashion unimpeded by an excess of ill considered restrictions.
natural odorants that are employed in perfumery can be assigned to
oils derived from the distillation of flowers leaves roots and fruits.
oils obtained by expressing fruits.
odorants obtained by the fractional distillation etc. of certain
(such as tinctures) of vegetable or animal origin.
the form of resins and balsams.
refer elsewhere to the conventional use of the smelling slip
the purpose of olfactory examination. For the comparison and selection
competitive samples of any specific essential oil or other odorant the
slip is once again indispensable.
and absolutes are sometimes loosely designated natural flower oils in
distinguish them from the distilled and expressed essential oils . They
obtained by different processes. For example the flowers leaves roots
subjected to a kind of extraction by hydrocarbon solvents which
waxes containing the odorous principles from the flowers. The
then eliminated by evaporation under reduced pressure so that the heat
affect the product so obtained which is called concrete oil or simply a
all these very delicate processes the constant care is to heat as
possible in order not to impair the product. Flowers for extraction are
gathered very early in the morning.
concrete of the flowers so treated has the appearance of a more or less
wax. It is insoluble in water and virtually insoluble in alcohol.
However it is
possible to make tinctures with it i.e. to dissolve by mixing in the
the odorous principles contained in the concrete by using enclosed
and 95° alcohol for a considerable number of days (about a month). An
product of great fineness is obtained displaying marked fidelity to the
of the flower. This is quite sensational particularly with jasmin and
great perfumes owe part of their fame to this practice which is
very great antiquity.
variation on the process was devised circa 1950 by the chemist Louis
It was based on ultrasonics and the energy which the latter liberate by
intense vibratory movements producing a series of pressures and
ringing about the bursting of the cells which liberates the esential
contained in those cells. The oils are then recovered but not
without some difficulty. One well known Grasse house has shown
interest in the process. It seems quite possible a priori that an
medium may be found for each type of product and that this will
recovery of the essential oils suspended in the supporting liquid. This
has at least the potential advantage of doing away with malodorous
of obtaining concretes or absolute oils that have not been overheated.
are generally obtained by extracting the concretes with alcohol then
eliminating the alcohol at reduced pressure. The product so obtained is
entirely soluble in alcohol and often has the consistency of honey.
concrete is subjected to extraction by alcohol by heating to the lowest
possible temperature in mixers. The product is then concentrated and
alcohol evaporated by heating to a low temperature and at low pressure.
called absolute essential oil is obtained which will be termed
the various extremely delicate operations of heating even slightly do
improve the quality and that is why in the case of jasmin the tincture
remarkable and irreplaceable bouquet. Thus every firm making natural
materials jealously guards the secret of its treatments processes and
operations which constitute the differences from the products of other
The precaution of not heating the extraction products in order to
freshness of odour has encouraged research workers to find new
few years ago a process was invented and perfected by Eugene Meunier on
of Messrs P. Robertet & Cie who registered the name of Butaflor
for all the
absolutes obtained by this method. The process is a low temperature one
consists of passing a stream of butane gas (boiling point 0 5°C)
through a kind
of tube in which the flowers are placed whose perfume is to be
absolute so obtained tends to be relatively light coloured and true to
in some cases it may not be entirely soluble in alcohol. This process
made it possible to obtain commercially interesting absolutes of lilac
of the valley.
very old process is that of the pomades. There were two ways of
of maceration in the hot state which consisted of melting an odourless
allowing the flowers to be macerated in it the fat or oil being kept at
medium temperature for the fat to be liquid without excessive heating.
absorbs the perfume. In the past forms of alcoholate were prepared by
extracting these pomades with alcohol in the cold state. Pomade
(lavages de pommade) were obtained which showed their concentration
to the number they bore.
extractions of these pomades with alcohol were carried out to obtain
concentrated solutions and the alcohol was evaporated in order to
produce the absolute
essential oils ex pomade.
all flowers can be treated by this process but only those which are not
delicate: the flowers of Cassie farnesiana rose orange blossom mimosa
of maceration in the cold state or enfleurage.
this process fat or oil is also used. It involves coating the glass
glazed wooden frames with a fat or oil. Inside these frames (termed
chassis) on the part coated with fat are placed the flowers. The frames
stacked on one another so as to obtain a hermetic seal and they are
stand for 24 hours so that the effluvia liberated dissolve in the fat
flowers that have given up their perfume are removed and replaced by
ones. This operation is repeated until the fat or grease is saturated
perfume. The perfumed fats are treated with alcohol and by increasing
extraction operations followed by chilling and filtration an alcoholic
is obtained which is subsequently concentrated by evaporation to yield
enfleurage essential oil.
flowers that have given up the greater part of their perfume in the
still contain perfume. They are treated with volatile solvents
or benzene) so that products are obtained which bear the name of
chassis ether type or absolute ex chassis benzene type.
flowers treated by this process are those which are the most delicate
in spite of all continue to live and yield perfume after they have been
These include jasmin tuberose jonquil narcissus and mignonette.
fats used are lard or vegetable fat. Pork lard is best and it is
deodorized. In these processes a small amount of fat is always carried
the alcohol. In the past this habitually gave when used in perfumes a
that was very slightly cloudy and which had to be chilled and filtered.
is at present possible to obtain extremely odourless fats some of them
synthetic. On the other hand there were once certain perfumers who were
opposed to the odour sui generis of these fats which contributed a very
suggestion of rancio (to use the special term adopted by perfumers in
part of this century).
Oils derived from Distillation
process is applied to flowers leaves stalks herbs roots and even to
are three main ways of obtaining these products:
in a still with naked flame. This was the former process. It continued
practised for a long time at artisan level in Bulgaria concurrently
steam process to obtain essential oil of rose. The essential oil of
rose obtained by this process then bore the name of Bulgarian peasant
(Rose Bulgare Paysanne) to distinguish it from that obtained by the
should be noted that the latter were introduced by the French (A.
Hasslauer et al.) and also by a few Germans. These were the processes
equipment used at Grasse with which the French had great experience.
naked flame distillation water was placed in the still along with the
ingredients to be distilled. It was heated to boiling point the steam
through a cooled coil and at the end of the coils the water and the
oil were collected. After a certain rest time the latter floats on the
(except in the case of a very few oils of higher specific gravity) and
separated from the water.
process is still used for certain plants for which distillation on the
more advantageous. These include lavender lavandin rosemary spike thyme
in this way the products treated have the advantage of being fresh and
process is to have large cylindrical stills heated by coils in which
circulates. It makes it possible to heat more regularly and to avoid
surges inevitable with naked flame stills. Water is placed in the still
the raw materials from which it is desired to obtain the essential oil.
heated and the steam is collected in more or less the same way as in
is the same as the previous one but a stream of live steam is passed to
still which carries the essential oils along more quickly. In certain
partial vacuum is produced which makes it possible to heat to a lower
temperature and to obtain finer products.
addition to leaves stems and roots citrus fruits are sometimes treated
way i.e. the peel of lemons and oranges. The essential oils obtained in
way are generally less fine and are above all used in the food and
industries. Some perfumers nevertheless prefer even for fine perfumes
distilled essential oil of West Indies lime to that of expressed lime
odour of this distilled essential oil is more characteristic finer and
interesting in use than that obtained by expression.
Oils Obtained by Expression
fruits that yield their essential oils by expression are the citrus
Hesperidaceae as they are termed in France (i.e. the fruit of the
garden of the
Hesperides islands which are supposed to have been located near the
or Canary Islands).
fruits include: lemons sweet and bitter oranges mandarins bergamots
from Italy or Africa the highly perfumed West Indian lime and the
these fruits whose essential oil is contained in the peel can be simply
squeezed out as they are. The whole of the juice of the fruit is thus
together with the floating essential oil. The drawback is that the
always acid and considerably impairs the essential oil.
the best processes are those in which the peel only is abraded to
essential oils contained in its cells. The oldest process now
not obsolete involved soaking up the essential oil with a sponge after
incisions in the rind. A number of mechanical processes have since been
and used to obtain citrus peel type essential oils economically and of
etc. from Essential Oils
products are midway between the natural products and the pure synthetic
products. An example will better show what is meant. From the natural
oil of Brazilian bois de rose is extracted linalool of which it
contains up to
90 per cent. This natural organic product has a sweet odour which is
and recalls the odour of the parent oil a slightly rosy and at the same
is a very important ingredient in perfumery which lacks the dryness and
of the products of pure chemical synthesis. That is why in our opinion
should not be assigned to the class of synthetic products but to a kind
special synthetic natural class.
problem of the pure and entire synthesis of the different aromatic
the chemical difficulties is governed by the cost of the synthetic
relation to the same product obtained by extraction from the natural
oil or by a modification of the natural product.
the example of linalyl acetate obtained from bois de rose linalobl and
synthetic linalyl acetate. It has to be admitted that for the perfumer
two linalyl acetates that having bois de rose as its origin is far
the other tends to suggest terpinyl acetate.
has often been an advantage in a complicated structural formula having
its chain existing in nature to take this part and construct the rest
However as the organic chemicals industry is developing more and more
day the possibilities of integral synthesis are becoming ever more
will not prevent the use in high class perfumery of isolates etc.
natural products. Sometimes even exceptional products are found e.g. a
bergamot linalyl acetate derived from bergamot oil and having a
subtle odour variation all of its own.
there is a whole class of products derived for different reasons from
oils and these are the deterpenated essential oils. Over forty years
perfumery chemist who caused a great stir at the time conducted
publicity for deterpenated essential oils in the sole French perfumery
that existed in those days. According to him all the essential oils
done away with and replaced by the corresponding terpene free essential
The latter are more soluble in alcohol than those which are not
it is therefore possible to concentrate more in a weakly alcoholic
But that is not the only criterion. The terpenes present in normal
oils play a part when incorporated in an alcoholic perfume that is far
negligible and appears to exalt the perfume as a whole. This is due in
least to the fact that in the scale of volatilities terpenes are an
link between the alcohol itself and the low boiling esters etc.
example has very often been cited of a perfume made with natural
and the same perfume made with deterpenated essential oils. Taking into
differences in strength that made with natural non deterpenated
is often greatly superior. Moreover what can a terpeneless oil of lemon
a perfumer when the natural essential oil contains 90 per. cent
the other hand some well produced terpeneless oils undoubtedly deserve
on the perfumer s shelves.
has been frequently stated that perfumes made with terpeneless products
deteriorate less rapidly but perfumers are not in entire agreement on
is carried out by fractional distillation at reduced pressure. It is
effected by appropriate solvents and other more recent methods.
Odorants as Tinctures
natural products are frequently employed in the form of tinctures based
their more or less prolonged maceration in 95° alcohol which is
hot or cold. Commonly found in this category is animal musk ambergris
and castoreum but other materials may also be treated in this way e.g.
patchouli leaves vetiver root oakmoss. The corresponding essential oils
absolutes are in most cases also available. Infusions are similarly
means of such treatments as processing in 95° alcohol in a heated
container fitted with reflux cooling equipment.
Vegetable Protein Meat
Meat Analogs can be defined
nutritionally equivalent to their biological counterparts however they
contain meat proiein or meat by products. They are developed to have
appearance texture and flavor of their meat counterparts. The proteins
analogs are derived from vegetable dairy and other non meat sources. On
other hand meat extenders are normally vegetable proteins added to
meats to supply nutritional and functional properties.
Foods was the modern day pioneer in the fabrication of meat analogs
introduction in June 1962 of SOYA MEATR a canned chicken analog. These
analogs were based on the Robert Boyer patent which employed the use of
soy fiber from soy isolate to impart a meaty texture.
are motivated to purchase fabricated foods for many reasons but the
factors are nutrition health convenience economy and variety. The
analog must meet the consumer s expectations in taste aroma texture and
the early 1970 s government and industry sources indicated highly
projections for sales of meat analogs. This optimistic forecast was
significant improvement by 1985 in the flavor texture and overall
composition of these products. However sales of this magnitude never
are many factors which influence the sales forecast for meat analogs.
flavor and texture of soy protein based analogs along with the inherent
flatulence factor were major drawbacks in early fabricated food
Significant improvements in the texture appearance nutrition and flavor
occurred over the last ten years and further improvements are being
However improved meat flavor for meat analogs would definitely increase
consumer acceptance. Consumers expect meat analogs to taste like their
counterparts. When this criteria is met sales of meat analogs will
significant factor in the food processing industry.
flavoring of meat analogs include the following topics: A) development
characteristic meat flavors B) properties of meat analogs as compared
and C) the application of meat flavors in meat analogs concerning
and processing. Flavoring meat analogs involves two related major
developing characteristic meat flavors and the application of these
OF CHARACTERISTIC MEAT FLAVORS
flavor of meat is attributed to a complex mixture of compounds produced
heating a heterogeneous system containing non odorous precursors which
develop volatile compounds non volatile compounds with taste properties
and synergists. An approach to the development of meat flavors involves
isolation and identification of volatile flavor compounds found in
identification of flavor precursors in meat and their role in flavor
biological processes in the development of meat flavor.
model systems that produce desirable meat type flavours.
are very complex investigations due to physical and chemical properties
and chemistry of the compounds. New analytical techniques have been
to pursue these investigations. In the last 20 years there has been a
tremendous advance in the understanding of meat flavor technology. To
majority of investigations by government universities and industry have
concerned with the basic understanding of the flavor of beef pork and
summarized the volatile compounds identified in Beef and Pork. In beef
6 acids 31 aldehydes 3 esters 1 ether 2 pyroles 25 alcohols 23 ketones
hydrocarbons 12 benzene compounds 11 lactones 8 furans 53 sulfur
37 nitrogen compounds. The compounds listed from pork are similar in
type. Chang characterized lactones furanoids sulfur compounds and
compounds which may be important contributors to meat flavor.
would think there would be more characteristic meat flavors available
type of investigation. However as compared to fruit dairy and nut type
flavor has not been found to contain a single predominant
volatile compound. In addition since the flavor of meat is the result
thermal processing the typical flavor varies depending upon the degree
length of heating. This also adds to the complexity of flavor
Just the number of volatile compounds identified poses a development
lists the aqueous meat flavor precursors which encompass fifteen
work indicates that the overall impression of cooked meat is the result
these organic precursors. Of the twenty three amino compounds
quantified in beef extract he concluded that Methionine and Cysteic
the most important amino acids contributing to meat flavor. It is
agreed that the development of volatiles responsible for typical meaty
is the result of non enzymatic browning reactions. These volatile
produced mainly from reactions of reducing sugars with amines amino
is uncertain what significant effect lipids have on the development of
aroma however it appears to be important in identifying overall
meat flavor. Flavor components are formed as a result of thermal
of the meat flavor precursors found in meat are the result of
reactions catalyzed by enzymes. Dwivedi reviewed anti and post mortem
factors relating to the development of meat flavor precursors. Post
tissue proteins degrade to release amino acids by the action of
proteases. In addition other precursors such as peptides nucleotides
carbohydrates also result from biochemical reactions. These precursors
important taste compounds. and also develop volatile compounds upon
and lipolytic enzymes have been used for decades for developing the
characteristic flavor of sausage. Free fatty acids liberated from
lipids by lipase provide the substrate for the development of carbonyl
These free fatty acids and carbonyl compounds are important in
of model systems containing precursors identified in meat and systems
containing compounds that may produce desirable meaty aromas and flavor
investigated. Shibamoto et al studied the reaction of D Glucose
Sulfide and Amnonia. Fifty one compounds were identified the main
being thiophenes furans pyrazines and thiazoles. Twenty four of these
were also identified in heated beef. By varying the levels and ratios
reactants the reaction products will vary in concentration and
This example demonstrates the utility of this approach in developing
patents have been issued covering the use of certain chemicals in meat
formulations. In addition patents covering flavor formulations
maillard and other reactions producing meaty compounds have been issued
the last 15 years.
though meat has been intensely investigated using modern technology
meat flavors have not been developed to satisfaction for meat analogs.
the reasons may be that the majority of the investigations concern beef
and poultry whereas meat analogs utilize other types of meat flavors as
in Table 2. Many of these meats are combi nations of various cuts and
meats fats and spices. In addition many home made recipes add to the
complication of characterizing these processed meats. One of the major
differences between meat and meat analogs is the development of
meat aroma upon consumer processing. This is caused by the level and
flavor added and the inherent chemical properties of meat analogs.
date the development of characteristic meat flavor includes the
combined use of
volatile compounds maillard and other selected reactions precursors and
enhancers and biological processes. Meat flavors for analogs must not
supply the characterizing flavor of the meat they must also mask the
the analog ingredients. Analogs that contain spicy flavors such as
hamburger are somewhat easy to flavor as compared to analogs that
delicate flavors like ham.
Aspects of Chocolate
The delicate flavor of a
chocolate bar is due to the
summation of skillful techniques. Fundamental knowledge has been gained
now on several unit operations which play an important role in flavor
development and in the final texture of the chocolate bars.
precursors .are developed in the cocoa beans during the fermentation
drying steps. Several analytical indices allow to follow changes in
induced by these operations: several ratios such as catechins/soluble
and soluble nitrogen/total nitrogen were shown to present useful
Varietal differences and changes in protein during pod ripening and
fermentation were characterized by detailed amino acid analysis.
changes during cocoa fermentation show a transformation of phases so
the end of the operation hydrophilic cytoplasmic constituents are
included in a
continuous lipidic phase. Classes of flavor precursors developed during
process were shown to include carbohydrates flavonoids catechins
and amino acids.
flavor of cocoa is developed during a roasting step where beans are
to a mild heat treatment. Main reactions during the roasting step
Maillard reactions Amadori rearrangements and Strecker degradations.
are particularly generated during the thermal process and their content
shown to vary according to the importance of the roasting temperature.
of thin layers of cocoa mass allow to characterize more precisely the
importance of time/temperature treatment in developing optimal cocoa
Free amino acids undergo also a Strecker degradation leading to
compounds which themselves may react to give aldol condensation
presence of 5 Methyl 2 phenyl hexenal an important flavor contributor
such wise explained. Some volatile sulphur derivatives may be
attributed to the
thermal decomposition of methyl S methioninesulphonium salt present in
cocoa. Important taste contributors to the bitterness of cocoa are also
developed by thermal cyclisation of peptides which play a synergic role
chromatographic techniques were used for characterizing the complex
mixture which contains important flavor contributors to cocoa aroma in
review we mention the use of differential gas chromatographic
allow to select constituents involved in specific flavors of cocoa
various origins. More elaborate mathematical methodology allows to
important flavor contributors by taking into consideration sensorial
data. For routine quality control simpler methods can be used one of
relies on measuring the ultraviolet absorption of steam distillates and
to characterize the degree of desodorization of cocoa butters the
milk chocolate samples and of various ingredients.
cocoa nibs are then milled the resulting cocoa liquor can be
using the same quality indices as those used for roasted cocoa beans.
liquor crystal sugar and milk solids are then mixed and refined
technological processes are used for this operation. Continuous lines
in use so that mixing comminuting and flavor development are optimized.
perspective in chocolate technology also involves multistage
obtain a smooth flavor of chocolate bar a last refining step called
applied during which some volatile constituents are lost and various
are dispersed so that the viscosity of chocolate mass is reduced the
conching time can be determined by the time at which lowest yield value
obtained. During the first 24 hours of conching strong changes in
sensory properties are observed but the particle size distribution of
particles is determined by the anterior milling and refining
particle size distribution plays a considerable role in assessing
acceptance to the consumer. Granulometric analytical methods reviewed
correlation experiments showed the importance of particle size
deter mining preferences of a taste panel.
conched chocolate mass is then submitted to a temper ing operation
which a suitable crystalline form of polymorphic cocoa butter is
operation can be analytically followed by applying a differential micro
calorimetric method. This precrystallization step will ensure a correct
hardness to moulded chocolate bars.
these physico chemical methods are however not sufficient for
overall quality of chocolate bars which can be only assessed by sensory
evaluation. Trained taste panel judgements may be expressed under the
flavor profiles. These judgements can then be submitted to
classification using for instance the principal component analysis.
statistical methods can also be applied. These mathematical
to characterize the censorial quality of chocolate bars.
Aroma of Various Teas
is one of the most popular beverages and there are many types and
teas available in the market of the world.
starting material for tea manufacture is the tender rapidly growing
of tea plant (tea flush) or tender young leaves.
teas are broadly
classified by the manufacturing process i.e. fermented tea (black tea)
fermented tea (oolong tea and pouchong tea) and non fermented tea
high acceptability of tea may be due to many factors but one of the
contributory factors seems to be its aroma.
aroma is determined by the quality of tea flush as well as the
manufacturing process. The quality of tea flush is largely influenced
season the geographical location and the variety of tea plant Camellia
amazing complexity of tea aroma components has been shown. They
aroma concentrate from black tea by capillary column gas chromatography
found that black tea aroma contains about three hundred different
order to find out the most important constituents which are responsible
tea aroma characteristics a number of research has been carried on and
investigations are gradually focused on a miner component. Thus the
number of compounds identified related with tea aroma arised to almost
to date as shown in Table 1. Here it may be said that the compound
reported year is later the amount supposed to be smaller.
such a numerous compounds have been identified from tea aroma real
components which determine the aroma character of various teas seemed
to be not
so large number.
paper deals with the aroma characteristics of several distinctive teas
Sri Lankan (Ceylon) flavory black tea Keemun black tea pouchong tea
and Japanese green tea (Sen Cha) and roasted green tea.table 1. Aroma
constituents of Tea.
process of black tea: withering à rolling à fermentation à drying.
the preliminary step to rolling resulting in a desired loss of water a
condition of the leaves which they can stand rolling without breaking.
wither is judged by loss weight (35 40%) softness and an agreeable
developed during withering.
object of the rolling is to impart the characteristic twist break the
cells and expose the juice to the air starting the oxidation of the
Generally the withered leaves are rolled twice the first rolling
50 minutes after that the leaves are sifted and the finer leaves are
into fermenting room while the coarser rolled again continuing for 40
with increasing pressure.After the second rolling the leaves are
screen and brought in fermentation process.
leaves brought into the fermenting room are spread evenly in shallow
trays in 5
cm deep and the room temperature should be kept around 25°C and the
humidity over 95%. During fermentation oxidation of the components in
leaves bring about chemical changes which largely determine the flavor
body and color of its infusion.
process has two purposes the one is stopping the fermentation and the
the reduction of water content to 4 5% at which level the tea can be
Tea (Sen Cha)
process of Sen cha: steaming à primary heating and rolling à rolling à
secondary drying à final rolling à final drying.
first step of the Sen Cha manufacturing is steaming by which the
enzyme in the leaf is inactivated and the green color of leaf can be
maintained. In the primary heating tea roller tea leaves are agitated
dehydrated by hot air introduced by fan from a furnance and taking out
loss of weight reached 48%. Then the leaves are rolled under pressure
minutes without heating and after taken out the lumps should be broken.
object of this rolling is to break the leaf cells and enable to
content of the leaves easily when brewed.
secondary drying in the tea roller (a trough placed over a heater) the
are reduced 68% of their weight for about 20 minutes.
rolling is performed in the final tea roller here the tea leaves are
under pressure and dried with the help of the heater beneath the
about 35 minutes the tea leaves is taken out from the final tea roller
leaves are dried again with hot air at about 65°C for reducing the
highest quality of pouchong tea is made only from the variety Chin shin
The tea flush is subjected first to withering by sun light for 5 20
withering indoors for 2 4 hours before the usual process of
pan fired green tea (Chinese green tea). The first step of pan fired
manufacture is parching in a pan at higher temperature about 230°C for
minutes. Then continue heating in the pan such a way that 150°C 10 min.
min. 100°C 30 min. 80°C 60 min. with repeating turn over the leaves. By
process the tea has a curly form.
AROMA COMPOSITION OF VARIOUS TEAS
Ceylon Black Tea
Sri Lanka (Ceylon) there are two well defined seasons during which
flavor is outstanding. These are Jan. / Feb. in the Dimbula District
July/Aug. /Sept. in the Uva District.
of the Top Note Aroma. Generally tea is evaluated its quality first by
of aroma which arises from tea infusion.
unblended black tea produced during the flavory season in Uva District
for our investigation.
concentrate which had a typical topnote or first perceptible
note of aroma from the tea infusion was prepared from the tea by
short time steam distillation (15 min.) followed by isopentane
constituents were identified by combined gas chromatography mass
(GC MS) and IR.
total of 57 compounds wore identified and approximate composition of
topnote aroma was determined as shown in Table 2.
constituents listed in Table 2 twelve miner components were recognized
there are still unidentified important components which will contribute
topnote aroma of flavory Ceylon tea composite mixture of identified
prepared based on the quantitative data in Table 2 seemed to improve
of commercial instant black tea to some extent.
is the result of the
transformation of a natural product the grape by alcoholic
fermentation. It is
quite remarkable to note that with this one term we group a variety of
whose organoleptic characteristics or flavor are extremely different
instance there is little resemblance between a Champagne and a fine
red wine or between a Sherry a Port wine and a Moselle wine.
characteristic of vinicultural production unlike that of any other food
drink is the vast hierarchy of quality and price that exists
the various types of production on one hand and wines of the same type
diversity of course expresses differences in chemical composition
for the differences in odor and taste but they are not always easily
distinguished by classical analyses. PEYNAUD points out the example of
wines having pratically the same basic analysis (alcohol acidity
although the price of one (Medoc grand cru classé) was twenty times
the other (ordinary table wine) an even larger scale of prices can
order to interpret the differences in odor and in taste which justifies
large price range it is necessary to explain the composition of wine
causes of its modification in more detail. Numerous natural factors are
involved in the constitution of wine: a) particular properties of the
the state of maturity c) eventual intervention of parasites which
the grape particularly Botrytis cinerea the fungus which causes rot d)
conditions of the alcoholic fermentation by yeast e) in certain cases
intervention of malic acid fermentation by lactic acid bacteria f) and
interventions always to be feared of chemical or bacteriological
we understand the complexity of the chemical composition of wine a
which has probably given rise to a greater amount of research and
study than any other food or drink. Although our knowledge is still
fragmentary we will try to indicate the current ideas concerning the
aroma of wine.
THE TASTE OF WINE
equilibrium of tastes
four basic tastes are found in wine a) the acid taste comes from the
organic acids whose free functions correspond to 100 meq/1 (N/10) b) the sweet taste which is
found even in
wines which contain no sugar is due to the alcohol and glycerol (8 to
10 g/l) c) the
salty taste is due to 2 to 4 g/l of
mineral salts d) the bitter taste comes primarily from the phenolic
and tannins (2 to 4 g/l in red wine).
quality of wine depends on the harmony of these different tastes one
dominate the others. In particular the acid and bitter tastes should be
balanced by the sweet taste the only one which is pleasant by itself.
which contain no sugar the alcohol plays an important role a solution
of 30 g/l
of ethanol has a sweet taste much like a solution of 20 g/l of
slightly alcoholic solution of saccharose is sweeter than a similar
red wine a demonstration can be given by separating the alcohol through
distillation or by steam distillation the distillate has a mellow taste
sweet which couples with the vinosity of the alcohol the stongly acidic
bitter residue is entirely undrinkable.
equilibrium helps explain why red wine rich in tannins and thus in
tolerate as high a level of acidity as can white wine whose level of
also has a relatively high level of acidity with a pH between 2.8 and
3.8 it is
the most acidic of all fermented drinks this acidity is linked to a
strong acid found in the grape tartaric acid. Such acidity is tolerable
because it is counterbalanced by the sweet taste of the alcohol since
also the most alcoholic of all fermented drinks reciprocally the
tolerable because of wine s high acidity. Moreover wine owes its
microbiological stability to its acidity and alcohol content which
certain conservation without the use of highly specific techniques.
follows from the preceeding ideas that wines especially red wines must
supple that is they should not have an excessively bitter or acid
taste. It was
thus found necessary to define a suppleness index which is explained
examples in table 1 an increase in the value of the index corresponds
increase in the sensations of volume softness and fullness of body
highly desirable in red wines.
suppleness index constitutes a relatively unique attempt to translate
organoleptic qualities by a relation which combines several elements of
chemical composition. The index could be improved upon as it remains
imprecise yet little work is being done in this field. Of course it is
that an increase of alcohol or a decrease of acidity would improve
every case these variations rapidly become excessive and the suppleness
is valid only within a certain compositional range. In addition the
employed are certainly not the best possible an increase in acidity of
probably has more effect on the decrease of sup pleness than a
alcohol of 1° GL. Also the total quantity of acid is not the only
involved in wine flavor the pH is involved as well as the nature of
instance succinic acid has a characteristic vinous taste.
hardness of red wines which is the opposite of suppleness depends upon
additional compositional elements particularly the level of acetic acid
andethyl acetate. When present in excessive quantities these compounds
indication of bacterial development and give wines particular
characteristics which reduce their quality. Even below the organoleptic
threshold (on the order of 1 g/1 for acetic acid and 150 mg/1 for ethyl
acetate) these compounds especially the latter intervene in sensory
on the aftertaste they reinforce the impressions of hardness and
suppleness index should take these compounds into account as well.
of phenolic compound structure
Suppleness Index and Examples of its Application
important element in the suppleness of red wines as well as in their
composition is the presence of phenolic compounds or more specifically
these compounds are involved in the taste not only by their quantity
by their nature which is not taken into account by the suppleness index.
are formed by the condensation of 2 to 10 elementary flavan molecules
(catechins). The polymerization level affects the tannins capacity to
with the proteins this capacity governs all of their properties in
results from a loss of the saliva s lubricating effect by denatuation
proteins. Thus as an example a tannin composed of 2 flavan dimers will
the same properties organoleptic in particular as a tannin composed of
tetramer even though the total weight remains the same.
polymerization of flavans can set off several mechanisms which lead to
with different properties. Other molecules as well (anthocyanins
polysaccharides) can intervene in the structure of these tannins table
a recent classification developed by GLORIES. Each class of phenolic
has its own organoleptic properties thus explaining the enologist s
which differentiates the good tannins which give both body and a
mellowness to the wine and the bad tannins which give wine an agressive
astringency. A precise chemical interpretation of these sensory
remains to be done they are related to the different tannin structures
cannot be distinguished by traditional analytical methods. High quality
varieties cultivated in reputed vineyards are distinctive precisely
they produce grapes rich in good tannins this characteristic dominates
tasting of fine red wines the variations between vintage years as well
a modification of tannins linked to the climatic conditions during
SULFUR CONTAINING COMPOUNDS
Patents 4 080 367 March 21 1978 and 4 134 901 January 16 1979 both
Lever Brothers Company describe food flavoring substances which can
food a savory flavor of roast or fried meat. These compounds have the
formulas in which Y is either a sulfur or oxygen atom and R1 and R2 are
hydrogen or an alkyl or hydroxy alkyl group having 1 to 9 carbon atoms.
of compounds of this class are: 4 mercapto 5 methyl 2 3 dihydrothio
phene 3 one
and 4 mercapto 5 ethyl 2 3 dihydrofuran 3 one.
of compounds of this class are: 3 mercapto 5 methyl 4 5 dihydrofuran
mercapto 2 5 dimethyl 4 5 dihydrothiophene.
of compounds of this class are: 4 mercapto 5 methyl tetrahydrothio
phene 3 one
and 4 mercapto 2 5 dimethyl tetrahydrofuran 3 one.
of compounds of this class are: 3 mercapto 2 methyl tetrahydrothiophene
and trans) and 3 mercapto 5 ethyl tetrahydrofuran (cis and trans).
of compounds of this class are: 3 mercapto 2 methyl 2 3
dihydrothiophene and 3
mercapto 2 5 dimethyl 2 3 dihydrofuran.
flavoring characteristics of compounds satisfying the above five
formulae and their tautomers were found to he particularly interesting
case where R1 and R2 represent a hydrogen atom a methyl group or a
like structure (1) except that the 4 position has a hydroxyl rather
mercapto group which may be used as starting furanone compounds to be
with hydrogen sulfide are for example 4 hydroxy 5 methyl 2 3
dihydrofuran 3 one
4 hydroxy 2 5 dimethyl 2 3 dihydrofuran 3 one and 4 hydroxy 2 methyl 5
3 dihydrofuran 3 one. Preferred examples of the pyrones which may be
with hydrogen sulfide are: 3 hydroxy 2 methyl 4 pyrone (maltol) and 3
ethyl 4 pyrone.
an illustration of suitable quantities of the flavoring substances that
added to specified types of foodstuff as little as 1 to 10 ppm w/w is
sufficient to impart a pleasant roast meat flavor to soups which are
otherwise lightly flavored. On the other hand when incorporating a
roast meat flavor to already flavored foodstuffs such as those based on
protein it may be necessary to incorporate larger amounts for example
to 8 000 ppm w/w of the flavoring substance in order to obtain a
1: Preparation of 4 Hydroxy 5 Methyl 2 3 Dihydrothiophene 3 one 140 g
available 1 butyn 3 ol (BP 107°C at atmospheric pressure) were treated
aqueous solution with 200 g of a 30% formaldehyde solution in the
10 g CuCI and refluxed for 50 hr. The resulting 156 g (70%) of 2 pentyn
diol (BP 115°C at 2.5 mm Hg) were isolated by evaporating off the water
distilling the residue.
g (0.5 mol) of 2 pentyn 1 4 diol were dissolved in 250 ml of dry
solution was stirred and cooled to 10°C in an ice salt mixture. With
cold solution of 286 g (1.5 mols) of p toluene sulfonyl chloride in 550
dry dichloro methane was added dropwise under exclusion of atmospheric
from the dropping funnel in such a manner that the temperature did not
After completion of the addition (about 1.5 hr) stirring at 0ºC was
for 5 hr and water (30 ml) was added in portions at intervals of 5 min
stirring and cooling so that the temperature did not rise above 5°C.
g of the yellow oil thus obtained (pentane 2 3 dione 1 4 dithioacetate)
dissolved in 1 500 ml of 0.5 N aqueous hydrochloric acid and stirred
for 1.5 hr
at 95°C. After cooling the reaction mixture was extracted five times
chloroform the combined extracts were washed with water dried with
sodium sulfate and evaporated to dryness affording a syrup which
on standing. After recrystallization from dichloromethane white
crystals of 4
hydroxy 5 methyl 2 3 dihydro thiophene 3 one were obtained MP 152° to
2: A_beef flavored composition was prepared by adding 250 ml of water
mixture of 5.7 g of 4 hydroxy 5 methyl 2 3 dihydrofuran 3 one and 25.0
cysteine and heating the mixture at about 100°C for 2½ hr. The
mixture was cooled and quantities of between 0.2 and 2.0 ml of the
mixture were sprayed over 100 g portions of dehydrated textured
protein containing no meat. An excellent roast meat flavor was thereby
to this material as assessed by eleven out of a total panel of twelve
maltose was added to a portion of the flavored mixture which resulted
reaction described above in an amount which provided a composition
about 70 pbw of dextrin maltose to each part of the substance
calculated on a
solid basis. The composition was freeze dried and a beef flavored
3: A mixture of 1.5 g of 4 hydroxy 5 methyl 2 3 dihydrofuran 3 one and
1.5 g of
cysteine in 30 ml of water was heated at about 100°C for 2½ hr. To the
resulting solution was added 33 g of maltodextrin. The solution thus
was carefully freeze dried. The powder obtained was used as a good beef
in soup or gravy.
4: 6.3 g of 3 hydroxy 2 methyl 4 pyrone 10.5 g of sodium sulfide
and 100 ml of water were heated together in a round bottomed flask at
the reaction mixture was added 117 g of maltodextrin. The resulting
was spray dried immediately. The powder thus obtained proved to have a
5: A mixture of 5 g 4 hydroxy 5 methyl 2 3 dihydrothiophene 3 one (cf
1) 0.5 g of hydrogen sulfide and 50 ml of water were heated in an
4 hr at 100°C and was subsequently allowed to cool. A product with a
meat flavor was obtained which was diluted to a volume of 1 liter
liquid meat flavor.
liter of water was added to the mixture and the whole was boiled for 5
soup so obtained was divided in two portions of 500 ml. In the first
150 mg of maltodextrin was dissolved and in the second portion 150 mg
flavor powder prepared according to Example 3.
soups were assessed in a paired comparison test by a panel consisting
persons. The soup containing the flavor powder had a characteristic
and was preferred by 7 out of the 8 testers.
Furyl Alkyl Disulfides
of sweet meat roasted meat liver flavors and aromas and hydrolyzed
protein like flavors and aromas has been the subject of the long and
search by those engaged in the production of foodstuffs e.g. luncheon
as liverwurst sausages. The severe shortage of foods especially protein
many parts of the world has given rise to the need for utilizing
sources of proteins and making such proteins as palatable and as meat
possible. Hence materials which will closely simulate or exactly
flavor and aroma of roasted meat products (e.g. roast beef like) and
products are required.
there are a great many meat containing or meat based foods presently
distributed in a preserved form. Examples include condensed soups dry
mixes dry meat freeze dried or lyophilized meats packaged gravies and
While these products contain meat or meat extracts the fragrance taste
other organoleptic factors are very often impaired by the processing
and it is desirable to supplement or enhance the flavors of these
foods with versatile materials which have sweet meat roasted meat
taste and aroma nuances.
4.098 310 July 4 1978 assigned to International Flavors &
have provided certain 3 furyl alkyl disulfides for altering the
properties of foodstuffs. These compounds have the formula:
Patent 4 066 710 January 3 1978 assigned to Givaudan Corporation
octadiene olfactory derivatives having the general formula.
the foregoing reaction scheme 2 7 dimethyl 1 3 7 octatriene of formula
converted into the sulfone of formula III using an excess of sulfur
the presence of about 1% of a polymerization inhibitor for example
3 tert butyl 4 methoxyphenol 2 6 di (tert butyl) 4 methylphenol (BHT)
After removal of the excess sulfur dioxide this sulfone of formula III
hydrated at the terminal double bond for example by the action of 40 to
aqueous sulfuric acid expediently at temperatures of 10° to 25°C. The
product of formula IV is neutralized (e.g. with sodium hydroxide) and
with a solvent (e.g. benzene).
removal of the SO2 protecting group and concommi tantly the
the conjugated double bond can be carried out by heating the compound
formula IV expediently in a vacuum and at temperatures 120° to 130°C.
has proved advantageous to carry out the heating of the compound of
in the presence of 1 to 2% of a high boiling organic base for example
ethanolamine or a tertiary amine such as a trialkylamine (e.g.
Inorganic compounds which have a weak basic reaction (e.g. calcium
can also be used.
esterification of the resulting alcohol (2 7 dimethyl 5 7 octadien 2
ol) can be
carried out according to known methods expediently by reacting the
a compound yielding the desired C1 5 alkanoyl group especially using an
appropriate acid anhydride such as acetic anhydride in the presence of
(e.g. pyridine sodium acetate etc). A corresponding acid halide can
be used for this esterification.
octadiene derivatives of formula I possess particular odorant
can accordingly be used in the perfume industry for the manufacture of
and perfume products for example for the perfuming of soaps solid and
detergents aerosols and cosmetic products of all kinds such as toilet
face milks make ups lipsticks bath salts and bath oils. In the finished
perfumes or perfumed products the content of the octadiene derivatives
within wide limits for example between 1% (detergents) and 20%
In perfume bases or concentrates the octadiene derivatives can of
be present in amounts greater than 20%.
octadiene derivatives provide in general a flowery especially lavender
without a fatty note. The free alcohol namely the octadiene derivative
formula I in which R represents a hydrogen atom possesses outstanding
qualities the odor thereof being pleasantly flowery (reminiscent of
like piquant earthy slightly metallic and long lasting. The
contain this alcohol have a powerful fresh action the alcohol being
suitable for flowery woody or hesperidine notes.
octadiene derivative of formula I in which R represents an acetyl group
possesses a natural flowery fruity green slightly woody odor which is
reminiscent of grapefruit and neroli and which is vetiverlike in the
background. Compositions containing this octadiene derivative
a very natural action.
ethers of formula I especially the methyl ether are readily volatile
and they can accordingly be used in perfume compositions especially for
octadiene derivatives of formula I can be advantageously incorporated
odorant compositions of the flowery type. Such compositions thereby
strength and cohesion and are thus modified in an advantageous manner.
following examples illustrate typical odorant compositions containing
octadiene derivatives provided by this process.
Patent 4 077 916 March 7 1978 assigned to Fritzsche Dodge &
have found that desirable perfume compositions can be made which
0.1 to 1% by weight hexyloxy acetronitrile and at least 1% by weight of
perfume component which modifies the olfactory properties of the
hexyloxyacetonitrile. The hexyloxyacetonitrile may be incorporated in
perfume composition in the form of a solution of dipropylene glycol.
compositions contain at least 0.1% by weight of hexyloxyacetaldehyde
hexyloxyacetonitrile utilized in these perfume composi tions is unique
olfactory properties. This nitrile has a flowery herbaceous slightly
reminiscent of irone. One of its outstanding characteristics is its
odor. Thus it is readily perceived and recognizable even from a
lasting power as determined from a smelling blotter is limited to 7 to
Accordingly it can be used advantageously to give top notes to perfume
compositions. It blends well with other perfume components to improve
character to the total odor profile.
hexyloxyacetonitrile may be used in a great variety of perfume
such as rose jasmine chypre lavender and phantasy bouquet. In such
it may be used in various concentrations to achieve a desired effect.
Consequently hexylo xyacetonitrile is a valuable addition to the
hexyloxyacetonitrile may be produced by the method described in U.S.
132 179 which employs the hexylo xyacetonitrile as a pharmaceutical
3 132 179 describes a procedure for the production of hexyloxyace
involving a two step method chloro methylating n hexanol to chloro
hexyl ether and reacting the ether with cuprous cyanide in accordance
following reaction scheme:
the hexyloxyacetonitrile may be produced by liberating hexyloxy
from one of its acetals such as its dimethylacetal reacting the
hexyloxyacetaldehyde with hydroxy lamine to obtain hexyloxyacetaldehyde
dehydrating hexyloxyacetaldehyde oxime for example with acetic
obtain the hexyloxyacetonitrile.
Patent 4 092 362 May 30 1978 describes a process for the production of
pentyl 3 (2 oxopropyl) 1 cyclopentanone and also perfume formulations
containing this substance.
n pentyl 3
(2 oxopropyl) 1 cyclopentanone is a valuable odoriferous substance
particularly fragrant magnolialike aroma. The production of 2 n pentyl
oxopropyl) 1 Cyclopentanone is accomplished by hydrolyzing and
a compound of the formula
hydrolysis and decarboxylation is conveniently carried out at a
from 120° to 300°C preferably from 140° to 250°C under substantially
reaction is conveniently effected using the same weight of water as of
pentyl 3 (2 oxopropyl) 1 Cyclopentanone. The reaction is normally
an autoclave from which the air is first purged.
reaction conditions for this step are those of a conventional Michael
condensation. The group R is conveniently an alkyl group and preferably
alkyl group having from 1 to 5 carbon atoms for example methyl or
ethyl. 2 n
pentyl 3 (2 oxopropyl) 1 cyclopentanone and its stereoisomers have a
strong odor of magnolia. Thus the compound can be used for the
perfumes as well as for the preparation of perfumed products for
and liquid detergents synthetic washing agents aerosols or cosmetic
all kinds. These odorant compositions may conveniently contain from 1
to 20% by
weight preferably 5 to 10% by weight of 2 n pentyl 3 (2 oxopropyl) 1
Substituted 1 Alkenynyl Cyclohexanols
Patent 4 088 681 May 9 1978 assigned to BASF Aktiengesellschaft Germany
obtained the 1 alkenynyl cyclohexanols of the general formula:
compounds of Formula (1) have a fresh woody and tart coniferous odor
and can be
used as constituents of scent compositions or to improve the odor of
products. Furthermore they offer a new and economical method of
obtaining the b
damascones which are popular scents since they can be converted simply
heating in the presence of acids to the corresponding b damascones.
the process for the manufacture of these substituted 1 alkenynyl
of Formula (1) cyclohexanones of the general Formula (2):
cyclohexanones of Formula (2) required as starting materials for the
conventional compounds which may be manufactured by alkylating
hydrogenating cyclohexanones which in turn may be manufactured from
ketones and a b unsaturated carbonyl compounds.
of Formula (3) which are preferable for use in the process are
enynes of Formula (3) need not be employed as such. Instead of using
in the presence of a strongly basic condensing agent the active salts
enyne may be used directly. This is very advisable for example when
unsubstituted enyne of the Formula (3) since vinylacetylene itself is
to handle. In that case sodium vinylacetylide for example is used it
obtained simply by the action of sodium on 1 4 dichloro 2 butene in
1: A solution of CH3MgCI in tetrahydrofuran (THF) is prepared by
chloride into a suspension of 19 g of Mg filings in 500 ml of (THF). 50
methylbutenyne are added dropwise thereto in the course of 50 minutes
The reaction mixture is then stirred until the evolution of gas has
g of 2 3 6 trimethylcyclohexanone are then added dropwise at room
and while cooling and the reaction mixture is left overnight while
stirred in order to complete the reaction.
ml of water are then added dropwise and the organic phase is decanted
and subjected to fractional distillation. 93.5 g (61% of theory) of 2 3
trimethyl 1 (3 methyl but 1 yn 3 en 1 yl) cyclohexanol of boiling point
72°C/0.1 mm Hg are obtained. The spectroscopic data confirm the
note: fresh herbaceous.
2: 28 g of 2 2 6 trimethyl cyclohexanone are added dropwise to a
sodium vinylacetylide (prepared from 25 g of 1 4 dichlorobut 2 ene and
15 g of
Na in liquid ammonia) in 200 ml of THF while cooling and the reaction
is stirred overnight at room temperature. 50 ml of water are then added
aqueous phase is extracted with ether and the resulting organic phase
and concentrated. Subsequent fractional distillation gives 5.5 g of
trimethylcylohexanone and 20.7 g (corresponding to 68% of theory based
ketone converted) of 2 2 6 trimethyl 1 (but 1 yn
3 en 1 yl) cyclohexanol of boiling point
62° to 63°C/0.3 mm Hg and refractive index nD25 1.4982. Fragrance note:
Patent 4 119 575 October 10 1978 assigned to Monsanto Company have
found that a
specific class of compounds having characteristic aromas which are
the preparation of fragrances are represented by the structural
represents hydrogen or alkyl having from 1 to 6 carbon atoms D and E
independently represent hydrogen or alkyl having from 1 to 6 carbon
that the sum of the carbon atoms in D and E does not exceed 6 provided
the bicyclo compounds at least one of A B C D or E must be an alkyl m
integer 1 through 8 F and G represent hydrogen or alkyl having from 1
carbon atoms X represents l (CH2)p J wherein p is an integer 0 through
2 and I
and J each independently represent hydrogen or methyl provided that if
p is 0
then m must be greater than 2 provided that the sum of the carbon and
atoms in the compound is no greater than 23.
1: 4 4 6 Trimethylbicyclo(4.2.0) Octane 2 ol – To a 2 liter 3 necked
fitted with a mechanical stirrer addition funnel reflux condenser and
tube was added 15 g (0.39 mol) of sodium borohydride and 500 ml 2
this solution was slowly added 218.6 g (1.317 mols) of 4 4 6
[4.2.0] octane 2 one in 50 ml of 2 propanol. After 2 hours about 200 ml
water was added. The mixture was stirred an additional 1 hour then
about 35 ml
concentrated hydrochloric acid was added. After another 1 hour of
ml of toluene and 500 ml of water were added.
layers were separated and the organic layer was washed three times with
of water. The combined water layers were extracted with toluene. The
layers were combined and dried over potassium carbonate. The solution
concentrated in vacuo and the residue distilled through a 25 cm Vigreux
to yield 215.8 g (1.284 mols 97.5% yield) of 4 4 6 trimethylbicyclo
octane 2 ol IR: 3360 cm 1. The aroma of the compound had camphor minty
and woody notes.
2: 5 5 7 Trimethyltricyclo [6.4.0.02 7] Dodecane 3 ol To
7.0g (0.19 mol) of sodium borohydride in
400 ml of isopropyl alcohol in a 1 liter round bottomed flask equipped
magnetic stirrer reflux condenser and drying tube is added 140 g (0.636
5 5 7 trimethyltricyclo[6.4.0.02 7] dodecane 3 one in 100 ml of
alcohol. The mixture is stirred for about 15 hours and then 300 ml of a
saturated aqueous sodium chloride solution containing 70 ml of
hydrochloric acid is cautiously added. The entire mixture is
transferred to a 1
liter separatory funnel and the layers are separated.
aqueous layer is extracted three times with 100 ml of petroleum ether.
organic layers are combined extracted three times with 100 ml of water
over magnesium sulfate and concentrated in vacuo to yield the product
viscous oil. 127.5 g of 5 5 7 trimethyltricyclo [6.4.0.02 7] Idodecane
3 ol was
recovered (0.572 mol 90% yield). IR: 3380 cm–1 BP 104º to 110°C/0.2 mm.
compound had a sandalwood aroma.
and perfumed products
are part and parcel of our everyday life. The demand worldwide for
enormous and constantly on the increase. At present over 300000 tonnes
chemicals and perfume oils valued at over 5000 million US dollars are
cosmetics washing and cleansing agents and other products. The perfume
has become a major business.
in earlier times perfumes were blended and their virtues extolled by
apothecaries perfumers or even charlatans since the mid 19th century
production of perfumes has gradually become manufacturing in character
now largely automatic and computer controlled.
PERFUME OIL FORMULA
oils are homogeneous clear mostly yellow tinted and often very complex
of natural and synthetic fragrances. Currently about 20 30% of the
perfume oils in terms of quantity is covered by natural substances and
by synthetic products. In terms of numbers there are well over 3000
liquid and non crystalline fragrances. Perfume oils generally consist
of 20 to
200 different components.
with earlier times it is far more expensive to mix perfume oils because
increased variety of substances and the vast number of complex perfume
formulas from the many products to be perfumed.
all perfume houses the perfume oil formulas are among the best kept
represent the know how. They play a major role in the success of the
Therefore access to the formulas is strictly controlled and numerous
provisions are incorporated. Earlier formulas were kept in safes but
now in the
age of computers formula safety is provided by card readers passwords
and the like. The metering and mixing processes naturally represent a
the security system. However careful selection of mixing staff and
coding of the individual fragrances and formulas minimize the risk. The
expanding use of computer control in compounding also increases formula
MANUFACTURE OF PERFUME OILS
manufacture of perfume oils means metering of the individual components
accordance with the formula followed by blending for homogenization.
view of the wide variety of individual substances and perfume oil
latter should be devised in such a way as to provide a logical sequence
products to be metered one after the other. The following method has
products with low volatility in liquid form
more volatile substances (aldehydes esters etc.)
of crystalline substances and resins (in some cases it may be wise to
substances at the beginning).
the current state of the art there are basically two different types of
metering volumetric and gravimetric metering.
metering devices work on the principle of displacement. The metering
quantity is not measured out produced by reproducible drive parameters.
is usually a relatively simple relationship between metering flow and
of the many volumetric metering devices include oval wheel meters and
pumps for liquids and screw type metering devices and star feeder
gravimetric processes the metering flow weight is constantly measured
density fluctuations have an effect in all metering methods with mass
measurement gravimetric metering is the most accurate.
appliances may fit the bill in a large number of cases especially when
special demands are made. However gravimetric methods have so far been
preferred for metering perfume oil components.
the production of perfume oils accurate metering of the individual
quality components is the decisive criterion for quality and hence a
of constant product composition.
is therefore the essential factor for quality assurance and materials
individual components are weighed by hand. In the past mechanical
(indicator scales) were used which did not permit data input and
recent years however electronic scales have taken over. Depending on
procedure the weighing system is fixed or mobile.
are installed and the individual components are brought from storage to
scales. Streamlining is provided in the form of rows of battery tanks
frequently used aroma chemicals with feed pipes to the weighing station
(product to scales).
are mobile and are moved to the individual storage containers which are
suitably arranged in battery tank rows (scales to product).
Automatic Metering on a Production Scale
complexity leads automatically to thoughts of how the conventional
process can be made easier.
first step towards automation
was to control the weighing system with punched cards. The aroma
flowed from the storage containers to the central metering stations and
metering was controlled in accordance with the given formula by punched
on which the component data were printed in the form of punch holes.
process has now been superseded by the rapid development of
electronic scales thus form the heart of the system and together with
mechanisms and computers provide the basis for a wide variety of tasks
well beyond the simple recording of weight. The use of electronic
systems can be seen from two main viewpoints. On the one hand weight
respective operating data are to be determined and further processed.
other there is the weight dependent control of the metering processes.
a basic parameter weight guarantees
composition of the individual substances in terms of quantity
monitoring of material consumption
control of sequences.
parameters for the design
of an automatic metering station are the required throughput (size and
of batches) and the requisite weighing accuracy for the individual
The time needed to make up a batch is known as the lead time which is
determined by the number and duration of weighing operations and the
control is the brain of the installation. It controls and monitors the
sequence and organizes the logging.
of automated equipment will depend by and large on data volume the
memory capacity and tae operating system.
process control and interlock circuits in metering installations are
achieved with the aid of programmable logic controllers (PLC) process
with and without external data memory ate used for formula management
dialogue and extensive recording.
on the production standard there are quite different ideas on equipment
and operating systems for weighing devices with integrated or
main function groups of metering control are:
comparison for coarse/fine metering per component with tolerance
metering time monitoring
functions data formulas
interfaces for peripheral equipment e.g. electronic data processing
Not so long ago it was
fashionable in some circles
to decry flower perfumes. Why it was asked should a woman want to smell
flowers? The exclusion of flower perfumes from perfumery has been
over a long period... The flower perfume is dead one writer asserted.
observations however tended to modify this initial impression because
on to praise some forgotten garden scents gave
suggestions for their formulation and
recommended their potential use as background odours in more
any extravagant statements to the contrary flowers and their perfumes
of very considerable and even basic importance to the perfumer. In the
place they are a stimulus a point of reference and a source of pleasure
invaluable information. In the second some of them are still
materials despite any disadvantage that may attach to them in respect
scarcity or cost. And in the third place many flower notes or floral
form part of the essential structure of even the most advanced and up
fantasy perfumes. The fashionable woman may not wish to smell like a
neither is she improved by smelling like a crude mixture of synthetic
or like a civet cat a musk deer or a dish of overripe peaches. The
perfume is after all a balanced blend of rather widely different
in it the floral note still plays a vital and even a dominant part.
shall be giving in this chapter for each flower mentioned a list of
constituents used in its reproduction including some that may be
thought of as
tricks of the trade although the main object will always be to approach
true note of each flower. Secondly we shall give one two or more
formulae by way of illustration. Here it is necessary to point out that
formulae can only be considered as the sum of the actual materials used
preparing them in the first place and that subsequent reproduction must
olfactory adjustments in order to give the desired result.
shall start with the more familiar perfumes based on flower notes.
notes vary considerably one from another. In addition to the basic
mentioned below under Red Rose. Damascene Rose and Centifolia Rose we
important auxiliary notes in the naturally occurring esters as well as
in a few
aldehydes and acetals. Many other odorants also enter in relatively
amounts but with significant effect into the composition of specialised
notes e.g. those of the tea rose Banksiana Zephyrine Drouhin and
Red Rose. This is usually
considered to be the
truest and finest type of rose odour. Its main constituents are
alcohol alpha ionone (as used by Coty in his Rose Jacqueminot) and the
useful nerol. A more flowery effect is obtained by the addition of rose
absolute and Bulgarian otto. Zdravetz or Bulgarian geranium oil can
obtainable impart a much appreciated green note.
damascena. Among natural essential oils this is represented by
The basis of this odour is given by rhodinot phenylethyl alcohol
palmarosa oil and cinnamic alcohol always in association with certain
essential oils and esters.
centifolia. The main constituents here are citronellol geraniol
alcohol and rhodinol together with smaller amounts of adjuncts which
give it a
slightly sharp note such as C9 aldehyde citral etc.
Rose. The basic components are citronellol phenylethyl alcohol and
The accessories that impart its special character include guaiyl
and tuberose absolute.
Marechal Niel. In nature this is a yellow rose with a very special
Basically one uses geraniol ex palmarosa oil citronellol and synthetic
in association with isoeugenol benzoin and sandalwood oil etc.
Rose. Here the base is rhodinol phenylethyl alcohol benzyl alcohol and
(to give it the slightly acidulated note by which it is identified).
is rounded off with a little bergamot phenylethyl acetate etc.
all matters relating to rose perfumes one has to take into
part played by Bulgarian Rose. This note is often required but
the widespread use of Bulgarian oil of rose in its pure state is
limited by considerations
of cost. This necessitates research into compositions de coupage i.e.
or extenders and these must be the best possible for the purpose. By
certain raw materials judiciously one can in fact arrive at some very
interesting extenders which will blend well with the natural oil giving
excellent quality of end product at a reasonable price. The raw
question are relatively few in number. One thinks of: phenylethyl
of geranium such as the Geranium incolore de Grasse geraniol rhodinol 1
citronellol and very small quantities of nerol and farnesol.
formula is given below. This is a convenient point to emphasise that no
can be better than the type and quality of its individual constituents.
therefore essential for perfumers to make their own trials and adjust
final formulae accordingly.
readers may be surprised to note the recurrence in certain of these
branded specialities usually made by some of the leading supply houses.
no apologies for these inclusions because they are in fact justified.
used because they contain new synthetic bodies that are not obtainable
market in the pure state while others are the result of the highly
blending of standard ingredients that it would be extremely difficult
consuming to copy.
this way one has at hand three different rose formulae all of a
approaching that of the Bulgarian Rose but each at a different price
Formulation over a reasonably wide price range is thus facilitated.
socialities are cited under the names of specific firms this simply
no one firm makes and criers exactly the same end product as the
each case one must take into account the fact that chemicals included
process as trace impurities are not likely to be present in exactly the
pattern or proportions in a competitive product.
of special shades of odour even among standard chemicals are provided
example by Givaudan s Laurine which is a hydroxycitronellal with a note
own often in great
demand and Lorcna
of Firmcnich which though a nerol is
yet distinguishable from other nerols.
footnote to rose compounding: modern perfumery now also makes use with
restraint of rose oxide.
and jasmin are still the most important flower notes used in perfumery.
or together they provide a conventional floral background for a great
of perfumes. Oil of jasmin has been the subject of much analytical
on this basis it is possible to devise a wide range of formulae for
Among the basic components one may note benzyl acetate amyl and hexyl
aldehydes benzyl alcohol formate salicylate and other esters indole and
derivatives phenylethyl alcohol dimethyl benzyl carbinyl acetate
linalool linalyl acetate ester? of propionic and butyric acids Peru
To sweeten formulae for artificial jasmins that may be somewhat crude
synthetic use can be made of jasmin absolute chassis which is the
obtained by petroleum ether or benzene extraction from jasmin flowers
previously been treated by the enfleurage process but which have
retained some of their perfume. This must not be confused with the
absolute of jasmin d enfleurage.
is a principle in fine perfumery that natural materials should be used
sweeten and soften the odours of synthetic blends. When costing
prevent the more liberal use of naturals the result of judiciously
incorporating even small quantities will usually prove conclusive.
composition has a rather fresh note that facilitates its use in
combinations both with other jasmin components and in perfumes where a
and fresh jasmin note contributes to the overall odour.
Production of Natural Perfumes
The perfume in the plant
perfumes one of the most marvelous phenomena of plant metabolism
their highest degree of excellence in the fragrance exhaled by fresh
This fragrance is due to the minute traces of essential oil which exist
petals sometimes in the free state as in rose and lavender and
the form of a glucoside which under favourable conditions is decomposed
presence of an enzyme or ferment as in jasmin and tuberose. The
existence of a
volatile oil however is by no means confined to the inflorescence but
frequently occurs in other parts of the vegetable organism.
example it is found in the
of cassie carnation clove hyacinth heliotrope mimosa jasmin jonquille
blossom rose reseda violet and ylang ylang.
and leaves of lavender rosemary peppermint and violet.
and stems of geranium patchouli petitgrain verbena and cinnamon.
of canella cinnamon and cassia.
of ceda linaloe and santal.
of angelica sassafras vetivert.
of ginger orris and calamus.
of bergamot lemon lime and orange.
of bitter almonds anise (both kinds) fennel and nutmeg.
or Oleo resinous exudations from labdanum myrrh olibanum Peru balsam
again different varieties of plants produce aromatic bodies of slightly
dissimilar odour as is shown by the numerous roses such as the red rose
white rose and the Marechal Niel while yet again the same plant grown
different conditions and in different soil will often yield an
essential oil of
entirely different bouquet as is demonstrated by the lavender of
Norfolk and of
France or by the geranium of Vallauris and of Bourbon.
these remarkable variations present a problem which has for many years
studied by numerous distinguished scientists among whom may be
mentioned Mer Mesnard
Maquenne Tschirch Dr Eugene Charabot and his co workers Messrs. Gatin
theories advanced by some of these earlier workers concerning the
the essential oil in the plant is worthy of note.
starches and cellulose were the starting point in resin formation
that of essential oils.
one of the greatest authorities on resins agree that the formation of
preceded that of the resins in the cell but that they were produced
materials accumulated in the membrane of the cells bordering on the
an earlier date however was of the opinion that essential oils were
products of chlorophyll. In the flower they are localised in the cells
internal surface of the epidermis where by photosynthesis the
converted into essential oils etc.
more recently thought perseite and other polyhydric alcohols containing
than six OH groups were the starting point in the formation of aromatic
these workers considered the essential oils to be excretory products
the metabolism of substances which functioned in the life of the plant.
considered further that their property of odour had a distinct
the functions of insects and of animals but very little to that of life
and Laloue in the course of experiments conducted over a number of
able to show that in many cases the essential oil did in fact originate
chloroplast and resulted from the assimilative work of the chlorophyll.
the formation of individual constituents of essential oils the
the generally accepted views:
formed first in the chloroplast.
by the action of acids on the alcohols in the chloroplast.
by dehydration of alcohols in the chloroplast.
alcohols by isomerization.
from the decomposition of proteins or from the oxidation of
from the rapid oxidation of alcohols principally in the inflorescence.
hastened during fecundation and growth of fruit.
probably in the same way as the aldehydes.
either from the splitting up of proteins or of aromatic acids.
problem of the evolution of these odoriferous constituents of the
kingdom embraces the following points:
formation and circulation of the odoriferous consti tuents.
evolution and the mechanism of that evolution.
of the perfumes themselves.
physiological influence on the plant.
a communication to the Academie d Agriculture de France Dr Charabot
these points most clearly by considering the perfume first in the case
whole plant and then in the case of the flower only.
says: When the plant is examined the odoriferous materials only appear
young organs and continue to form and accumulate with decreasing
blossom time by diffusion they go from the leaf to the stalk and thence
During the process of
fecundation a certain
quantity of essential oil is consumed by the inflorescence and as a
consequence the gathering of perfume producing plants should be made
before fertilisation is accomplished. Once this process is complete the
fragrant principles redescend into the stem and diffuse into the other
migration being stimulated by drying of the inflorescences which
osmotic pressure and partially precipitates the less soluble products.
In considering the flower
only it is known
that certain varieties (after collection) produce fragrant bodies when
in such a condition that their vital functions may still be exercised
other cases the flower contains all its odoriferous principles in the
state and it is impossible for it to produce new fragrant materials
it be still living.
conclusions arrived at by Dr Charabot after a study of the evolution of
odoriferous compounds and of their mechanism are as follows: The esters
frequently found in essential oils are formed in a particularly active
in the green part of the plant by the action of acids on the alcohols.
phenomenon characteristic of the chlorophyll region is influenced by an
a diastase of reversible action which functions as a dehydrating body.
influences capable of modifying the plant in order to adapt it to an
chlorophyllic action at the same time aid the formation of esters this
favourable to the mechanical elimination of water.
Thus the functions of
chlorophyll tend to
acquire a new significance not only do they assure the fixation of
acid gas by the vegetable tissues not only do they in assisting
the circulation of the liquids which bring and distribute the materials
necessary to the mineral nutrition of the plant but they also during
assimilation of carbon actively assist condensation enabling the
of a simple chemical body into one of those innumerable complex
study of which has puzzled the shrewdest chemist.
When the alcohol is in the
proper state to
easily lose the elements of water it gives birth to the esters and the
corresponding hydrocarbon at the same time or briefly put the first
transformation takes place in the chlorophyll region by way of
On the appearance of the
flowers (those organs
in which the fixation of oxygen by the tissues is particularly intense)
possible that the alcohols and their esters are converted into other
products the aldehydes or ketones with at the same time the liberation
energy necessary for fecundation.
A large number of
odoriferous materials varying
greatly in their functions and their chemical structure may be produced
splitting up of glucosides. When the generality of such a mechanism is
it is easy to give an explanation of the observed facts relating to the
formation of odoriferous materials and to their sudden appearance in
that part of the vegetable organism. If the glucoside which is formed
green part of the plant immediately encounters a medium whose
favourable to its decomposition the essential oil appears there at once
begins to circulate to perform evolutions and to play its part. In
other cases the
glucoside will only meet the ferment capable of splitting it up in the
Only after having circulated in the plant and reached the flower being
more or less the whole way will the glucoside be able to liberate the
constituents of the essential oil. The flower only will then be
The formation in certain flowers of new quantities of essential oil in
proportion to the quantity of essence removed is explained by the
chemical equilibrium resulting from the reversible reaction.
The production of essence
ceases when the
state of equilibrium is attained. But when the odoriferous material is
in proportion to its formation the reaction of division can go on until
whole of the glucoside is decomposed. From these conclusions it will be
understand their application in the extraction of flower perfumes
regard to the physiological influence of the aromatic materials it was
formerly that they were of little use in the vegetable organism. It has
noticed by Dr Charabot and his co workers that on the contrary they can
employed by the plant especially when the latter is sheltered from the
and does not assimilate the carbonic acid gas of the air with the same
They participate in a normal manner in the work of fecundation and of
of the seeds during which time they are partially consumed. Other
put forward to account for the part played by the essential oils in the
the plant are as follows:
and Ravenna think they may act as hormones and thus act as excitants in
fecundation of the flower.
considers them to be waste products because they are generally toxic
lower organisms and for higher plants. Tschirch thinks they are waste
from which the resins are formed and are therefore incapable of
again in the plant.
takes the view that odour is more effective than colour for attracting
laden insects but that the essential oil has other functions is not
suggestion that the volatile oil may be a protecting agent against
parasites will not hold water because unfortunately odoriferous species
just as much subject to invasion as non odorous plants.
leaving the subject of plant metabolism let us take a concrete example
of the marvelous
changes which occur in the composition of an essential oil namely that
produced by the orange plant. If an essential oil is distilled from the
inflorescences when they are in full flower and before fecundation has
place the product will have a comparatively high content of esters and
oxygenated bodies and be relatively low in terpenes.
the orange flowers are fertilised and the fruit allowed to develop
essential oil is obtained on distillation that contains much less
constituents and a larger proportion of terpenes than the oil distilled
the fresh flowers.
supposing the fruit is allowed to become fully grown and the essential
expressed from the mature peel it will be found that the oxygenated
constituents have decreased to an almost negligible percentage and
has been taken by terpenes.
on Flower Perfumes
is the name of an extensive genus of trees and shrubs of the N.O.
in habit from heath like shrubs to lofty trees and widely spread
tropical and sub tropical regions of both hemispheres. The
the form of compact globose heads or spikes of various colours
generally white pink
or yellow the latter being the predominant colour in the Australian
India the genus is represented by about eighteen species of trees of
sizes distributed throughout the country some attaining a height of 100
in the forests of Pegu and Prome. In Western Asia and Africa the genus
represented by gum yielding species such as A Arabica and A Senegal
small sized thorny trees of forbidding aspect and frequently occupying
tracts of desert country. Other species of acacia are also common in
Indies and tropical America where they are valued for their timber. In
Australia this genus is profuse and as many as 300 different species
recorded several of which are of great commercial value as the bark is
tanning. Among the more important of these are Acacia decurrens known
black wattle in Victoria and Tasmania A. dealbata the silver wattle and
pycnantba the broad leaf wattle. In southern Europe and western Syria
is represented by A. Julibrissin and A. Farnesiana. In this country the
of France and northern America the trees generally but erroneously
as acacia are Robinia pseudacacia having aromatic white flowers which
during May and June and impart a pleasant odour to the avenues and
adorn. Originally a North American species the tree was introduced into
some 250 years ago and is today much admired. It attains a height of 40
feet and averages 2½ feet in diameter.
acacias possess sweet scented flowers and of these (with the exception
Farnesiana and A. dealbata which will be dealt with in separate
more important are A. biflora and A. bastulata. The odour of the former
the coconut while that of the latter resembles hawthorn but as far as
neither have been turned to practical account for the extraction of
perfume in Europe. In Australia however there is a perfume known as
obtained from the flowers collected after sundown. It is prepared by
them in olive oil which when saturated is extracted with strong
odour of the flowers of Robinia approximates more nearly to that of the
bastulata and will therefore be taken as the standard flower for its
flowers of Robinia pseudacacia have been subjected to an examination by
who extracted the blossoms with a readily volatile solvent and obtained
dark coloured oil with a peculiar basic odour which when diluted repro
natural flower fragrance. This oil contained 9 per cent of ester
methyl anthranilate. In alcoholic solution it gave a clearly
fluorescence and on dilution with ethereal sulphuric acid yielded this
substance. The following further constituents were also identified:
benzyl alcohol linalol and a terpineol. In addition aldehydes and
a decided odour of peach and probably also nerol are present.
perfumes as distinct from those of cassie and mimosa are characterised
intense flowery fragrance that is reminiscent of a blend of hawthorn
orange blossom. A rich bouquet may be obtained by combining these
compounded oils or if a basic note is required on which to build the
may be secured by mixing anisic aldehyde with methyl anthranilate in
of 4 to 6. But since the latter is rather harsh a part of it may be
with advantage by methyl naphthyl ketone in which case the note may be
off by the following vital constituents:
notes. Benzyl acetate Linalol Terpineol Bergamot Methyl cinnamate and
petitgrain. Middle notes. Clove Ylang Jasmin Rose and Neroly. Basic
ketone Santal and Vetivert.
Greek philosopher Theophrastus in his Enquiry into Plants VI 6 2 states
the gillyflower (? stock) is sweet scented but that the carnation and
wallflower are scentless from which it is evident that this flower was
the fourth century B.C. There appears to be no clear record of the
of the carnation into Britain some writers stating that it came from
others that it was imported from Italy and the shores of the
There is no doubt however that the spicy fragrance of the flower has
appreciated for centuries throughout Europe and was very much favoured
time of Queen Elizabeth.
clove pink Diantbus caryopbylus of which the carnation is a variety is
leaved herbaceous plant of the N.O. Caryophyllaceae. The origin of the
is worthy of mention. It is derived from the French word clou English
clout a nail from
the imaginary resemblance of the
clove flower to the head of a nail. Tournefort a French botanist who
1708 is supposed to have given it the specific name Caryopbyllus on
its similarity to some of the short leaved species of the genus C arex
allies. The word Caryopbyllus is also applied to the molucca clove
there is no likeness between the two nevertheless Tournefort s name of
Caryopbyllus aromaticus was adopted by early botanists for this well
spice. This consists of the dried unexpanded flower buds of a tree of
Myrtaceae which is now known as Eugenia caryopbyllata.
are over fifty species of Dianthus with numerous varieties believed by
horticulturists to exceed 2000 and including carnations pinks picotees
sweet williams. Some of the well defined species are:
beautiful but inodorous.
Barbatus the sweet william.
Hortensis the garden pink.
Plumarius tiit pheasant s
Deltoides am D. Caesius both
are grouped by florists according to markings of the flower as follows
spotted or striped with several shades (usually three).
markings on coloured grounds.
two colours striped longitudinally.
with tinted petal edges.
referring to the catalogues of any of the well known horticulturists
be found hundreds of these varieties of carnations and like roses they
known by all sorts of fancy names. From the point of view of odour
carnations are generally to be preferred to red ones. Along the French
Italian Rivieras very large tracts of land are devoted to the
these exquisite flowers. Visitors will have noticed them in particular
Nice and Antibes and also near Venti miglia Bordighera and San Remo.
blossoms begin to appear as early as September and continue until July.
major portion of them are sold as cut flowers and sent to Paris and
an indication of the importance of this business it is interesting to
a substantial number of carnations are sold annually by French growers
lesser amount by the Italians.
carnation has developed its rich spicy odour with cultivation although
it is a
peculiar fact that horticulture is responsible for many beautiful forms
are almost devoid of perfume. In the wild state it seldom possesses
these qualities and is occasionally found growing on dry soil.
as stated above large quantities of carnations are grown in the south
by far the greater proportions are sold for decorative purposes. In
parts of the Var near Grasse the flowers are grown especially for
purposes. Those of importance are white pink and red and yellow and
harvest takes place in June and the blossoms are picked after exposure
three hours of brilliant sunshine. The perfume is then at its maximum
fragrance. It is extracted nowadays almost exclusively by means of
solvents. About 500 kilos of flowers yield 1 kilo of concrete. This has
high wax content and the yield of absolute is in the region of 10 per
only. This has a waxy odour of heavy carnation type and is eminently
sophisticated perfumes. In Holland a quantity of carnations are grown
perfumery purposes and are extracted by volatile solvents.
distillation 1000 kilos of carnation flowers yield 30 grams (0.003 per
a pale green solid having an intense odour resembling that of the nine
carbon atom aldehydes. On extreme dilution this develops the true
chemistry of carnation flower oil has not received much attention
owing to its meagre yield. However it has been studied by Glichitch who
isolated from the distilled extract 31 per cent of stearophene which
to be identical with heptacosane. He removed traces of an aldehyde when
residual oil had an odour reminiscent of cinnamyl and citronellyl
Treff and Wittrisch experimented upon clove pink blossoms grown at
Saxony. They extracted 2.840 kg of flowers with petroleum ether and
yield of 8.0 kg = 0.289 per cent of solid extract. This was treated
alcohol to remove inodorous matter yielding 2.5 kg 0.088 per cent of
extract. This was finally steam distilled to yield 122.65 grams =
are based largely upon the isolates and synthetics derived from clove
which eugenol is much favoured owing to its fragrant peppery character.
Salicylates are also indispensable constituents and the vital natural
ingredients are the rose alcohols ylang and Peru balsam reinforced with
orris absolute or carrot seed oil.
Farnesiana is a small tree whose origin appears to be uncertain. It is
be a native of San Domingo and became naturalised in Europe in the
at Rome about 1656 but this date is probably incorrect since it is
by the author of a book published in Rome in 1625 entitled Albini Hort.
Fantesiana. About 1764 Linnaeus in Honrt Upalensis described and named
Mimosa Farnesiana which was afterwards by Willdenow placed in his genus
waters have been in use since the days
of Theophrastus and are believed to have hygienic qualities not
ordinary handkerchief perfumes. It is difficult to explain their
since they are generally made with weak alcohol but as the diluent
consists of rose or orange flower water it may be that this to some
any rate accounts for their designation.
distinction is however
noticeable in nearly all modern formulae
and this is the
absence of any flower extract the principal constituents being either
distillation or expression products. In the formulae which follow it
noticed that the citrus oils play an important part even in lavender
the best effects are obtained by the liberal use of bergamot oil in conjunction with of course
either English or
French lavender oil.
water was probably the earliest
member of this series and is said
to have been used by the ancient Greeks as a tonic
for the hair. In later years it was prepared by distilling a
mixture of honey gum arabic and water and was
employed as a lotion for the face which it made white and fair . Nearly
modern formulae are based on the product originated by George Wilson
manufactured it for King James II.
the musk and
ambergris in a glass mortar and afterwards put
all together into a large matrass and let them circulate three
days and three nights in a gentle heat let them cool. Filter and keep the water in bottles
water was popularised by Sir Erasmus Wilson who prescribed it
as a hair wash. The following formula will make a pleasantly perfumed product
such as is in demand today:
This may be prepared as described under eau de
Cologne when an
excellent product will result but if distilling apparatus is not
whole should be macerated at least six months and afterwards filtered.
water is another eau
and was prepared mainly from rosemary. The fresh herb was
taken and distilled
with spirit variations
being sometimes made by
the addition of lemon lavender or orris. There is very little call for
this product today but as it may be of interest
formula is appended:
Eau de Cologne
all the toilet waters sold to the public none
are so popular as eau de Cologne for it is known universally. There
be some doubt as to the actual origin of this
perfume and according to one version ir was invented at Milan by Paul
Feminis who manufactured it at Cologne in 1690. This gentleman is
have given the formula to his nephew Jean
Farina who commenced to make
it at Paris in 1806 and the manufacture of this particular eau de
supposed to be continued there today by a well known firm. Another
probably the correct one appeared in a
well known English periodical many years ago. According to this account J.
M. Farina who
was the veritable
inventor of what he called Kolnisches Water or as it is much
elegantly designated in its French synonym eau de Cologne was an Italian by
birth born at Santa Maria Maggiore in the
valley of Vigezza district.Domo d Ossola in the year 1685. He had
emigrated to Cologne however and became a naturalised German changing
name to Johann at a somewhat
Certainly he was in business opposite
the Julich s Place in the year 1709 for his commercial books back to that date
in the possession of
the firm. Kolnisches Wasser is among the entries at that period so that
perfume has been in existence certainly
since that date. In 1726 the trade was flourishing for in that
sent for his brother John Baptist from Italy who became his partner. The
latter died in 1732
and John Maria who was unmarried found himself again
alone. Then he sent
for the son of John
Baptist who was
own godson and was luckily
named John Maria from Italy and gave him
a partnership. In 1766 the original old gentleman died
and left the
to this John Maria the
second. This one lived till 1792 after which his three sons John
Maria and Charles Antony Hieronymus reigned in his stead.
The middle one
of these who was
obviously intended to be
the survivor of them all perversely died first and so for
a moment the
famous name was lost to the firm. But the other brothers both named
eldest sons John Maria/
and these ultimately succeeded to the proprietorship
of the business. The son of John Baptist died in 1833 but the other
became head of the house. His son who was also named John
Maria was actively
associated with the senior Mr.
Farina in the conduct of the business. The word Farina appears on
of eau de Cologne and this is not surprising
since the name is a common one in Italy. At the present time
there are two or three perfumers in Cologne who claim to be
the original makers of this favourite toilet water. There is
about all the old
fashioned eau de Colognes which is that they represent a type
or less citrus bouquets blended with rosemary or
lavender. They possess
a refreshing and incomparable fragrance which is typical of all the
purity and source of
the alcohol employed as a solvent for the
oils is a factor which contributes materially to the odour of the finished perfume and a
perfectly neutral and
highly rectified potato spirit is undoubtedly the most
useful for this
purpose. If this should not be available a treble distilled molasses or
alcohol will make a good substitute. The mere traces of oenanthic ether
are present in these specially prepared raw materials appear to blend
the oils and slightly modify their
odour. The oils used
selected from the few rather than the many possibles and
may include neroli petitgrain lemon orange
and bergamot with the judicious additions of lavender and either
also plays a most important role
in the manufacture of de luxe products
but the oil of neroli should always be added afterwards. This process
very subtle influence upon the fragrance of the constituents and an
different and finer product results. The reasons for this peculiar
only be conjectured but that some molecular reconstruction of the essential oils takes place
appears to be most
probable. When distilling apparatus is not
available the oils should be dissolved in the strong alcohol and the
little by little. The mixture is then placed aside in tanks when
terpenes are precipitated. This process may be hastened by freezing and
immediate filtration yields a brilliantly clear liquid which will not
under any conditions. A reference to the odour classification which follows will
suggest other basic notes together with a long
list of all aromatics that may be used in the creation of this complex.
are a few firms who still use rectified spirit for their toilet waters
the availability of better quality alcohol in Britain a different
has been placed upon the manufacture of all perfumery. For the
formulae the oils are merely added direct to the alcohol. Since the
is of minor importance maturing of the finished product for any period
which closely resemble the original
may be made as follows:
Flavourings and their
requirement for liquid refreshment is as longstanding as the origins of
homo sapiens. An examination of Figure 1 shows that at relatively low
fluid loss e.g. 3% impaired performance results. A 20 30% reduction in
for hard muscular work occurs with a moisture/fluid loss of 4% heat
at 5% hallucinations at 7% and circulatory collapse and/or heat stroke
fluid loss. The required fluid intake for
the average person in the arid areas surrounding the Red Sea is a
litres per day.
With the very existence of life depending on our
fluid intake why do
we not simply take water alone? The first reason is that water alone is
readily taken into human body systems as it requires a certain level of
carbohydrate and salt for rapid transfer across the brush border of the
The second reason is that water alone is uninteresting and unquenching
The importance of fluid intake at the correct
osmotic pressure (a
measure of tonicity and hence compatability with body fluids the
being isotonicity) is at the very origin of hum nutrition. What was the
for the original manufacture of local wines ut alcohol contents of
approximately 5% in the tropical subtropical and arid areas of the
was simply to use the preservation properties of alcohol as a means of
grape juice from degrading to a non potable state. In the process
fluid (water) was held in a microbiologically stable and acceptable
suitable for use over extended periods of time. This was the origin of
category of food products that has the universally accepted
early days of wine production it was found that by using different
and fruit juices in varying proportions a multitude of completely
tastes was achievable. The occasional use of only small quantities of
fruits vegetables or herbs with strong characters (e.g. mango or thyme)
blend of juices to be fermented would result in a completely different
the finished wine. This was probably the first
regular use of the application of food flavourings to
substance which when added to a beverage in quantities lower than 50%
total volume causes the flavour of the whole product to assume its own
character may technically be called a flavouring. However we will
flavourings only in passing and concentrate our discussions on intense
low volume use flavours one of the problems when trying to discuss the
composition and appli cation of food flavourings to beverages is the
diversity of beverage industries around the world. An overview of some
major sectors of these industries is presented in this chapter.
composition of either naturally occurring
or synthetically produced flavouring
material must now be examined closely for compatibility with the
category of beverage that requires flavouring. For example some of the
effective and readily available
materials are citrus
essential oils released from the peel of citrus fruits during
processing for juice extraction. These oils as obtained
from the fruit
are almost insoluble in aqueous and aqueous sugar containing beverages
generally soluble in high alcohol containing
beverages and have limited solubility (but greater miscibility)
in aqueous beverages with sugar
contents higher than 60%. These solubility/miscibility
characteristics are predictable from an examination of the composition
shows a very high water insoluble tcrpcnc content. The
both lemon and orange oils is given together with information on
extraction requirements in
composition for the natural whole citrus oil which has been
neither solubilised nor processed is thus
a high alcohol containing beverage with a high sugar content. This is
called a liqueur. Many famous
names in this
beverage category are renowned for their strong fresh authentic citrus
would be almost
impossible to obtain via any
other flavour route since the other methods which we shall consider for
of these and other such essential oils result in a diminution in authenticity of character
compensated for in other ways.
Types of Flavourings for
as there are broad
compositional categories for
beverages so it is with flavourings
for beverages. They result from either the form in which the concentrated natural or
exists or result from the method or
methods used to extract or manufacture the flavouring.
the flavourist is
compounding a flavour he will start with an array of flavouring
either natural or synthetic origin. These components will have
physical performance characteristics of dispersibility and solubility
as individual flavour effects and interactive properties with other
For natural flavouring materials these properties will in part be the
the method of extraction and solvents used and will fall into
three broad categories or types which then
result in two basic performance
type by solvent
of (a) and (b) for
performance reasons and generally operating at the limits
The synthetic components
will also carry with
them performance characteristics which may be categorised in a similar
Solubilisation and Concentration of Flavourings
water (a lone) soluble flavourings are by far the smallest category for
flavouring of beverages it would seem sensible to consider these before
soluble and mixed solvent flavourings. Their acceptability and ease of
the aqueous non alcoholic beverage category and industry (as defined in
chapter) would make them the preferred route for flavour application if
not for the limitation they impose on flavour range and intensity. The
and most widespread extraction and use of water soluble flavourings is
of Coffee Flavour and Manufacture of the
is prepared in a series of column extractors in which the finely ground
beans are extracted with counter currents of water under pressure at
(350°F) for a period of about 4 h. This results in an almost complete
of soluble solids from beans and gives about 45 50% of extract. The
concentrate is then either spray dried to give the familiar free
or freeze dried and agglomerated to give a product looking more like
coffee. To improve the freshly perked or filtered coffee aroma about
recovered coffee oil is incorporated into the product by either
the surface of the powder or by incorporation into the concentrate
freeze drying. The resulting products are packed under inert gas into
jars to protect flavour freshness and intensity during storage prior to
this example of what
appears on the surface to be a fully water extracted and soluble
system we can already see that certain very important and significant
(taste and in particular aroma) components are lost if only the water
alone is used. This is because when any flavour extraction is carried
temperatures of 100°C and above (at atmospheric pressure) any essential
and dependent upon temperature resinous materials will be volatilised
carried over in the steam released. The effectiveness of this volati
must be compensated for when formulating the finished beverage will be
dependent upon the particle size of the material under extraction since
has to be small enough to allow good steam penetration. This can be
more clearly in the next most commonly perceived water soluble or
of flavourings concentrated fruit compounds and flavouring extracts
flavour of the fruit is divided unequally between the juice and the
and oil components.
Flavourings Extracted from
are the matured
ovary of the plant or tree and may be with or without seeds
and sometimes with the flower still
attached. The wall of the fruit developed
from the wall of the ovary is called the pericarp and may be either dry
fleshy it is this edible fleshy part which forms most of the varieties
we call fruits
. Nuts are also fruits and they will be covered separately
for their application to beverages and in particular the
cola nut extracts
Botanically fruits may be classified as in Appendix II.
is the type of classification and way of
thinking about fruits that a beverage
formulator will pursue as it follows the perception and requirements of
consumer. A flavourist however will be more interested in the value
and intensity of the flavouring materials as library items from which
when compounding flavourings. He or she may be less interested in the
replication of the whole fruit flavour in the finished beverage this
being the job
the applications technologist. The processing of fruit for the purpose
extracting juice is a complex area of technology involving the use of
different expression techniques de activation of natural enzymes
processing and flavour retention collection and recovery techniques. A very full
account of fruit
processing has been also been given by Tressler and Joslyn and will
covered in outline here as far as it
relates to flavour extraction formulation beverage application and
little flavouring which
may be obtained from natural materials for beverages can be extracted
dissolved by water alone. In citrus fruits the juice cannot possibly be
characteristic of the whole fruit since so much of the character is
in the oil component in the peel.
so called berry fruits
the method of hot enzyming and extraction ensures that the volatile
components will be lost during concentration in the steam/water phase
steps are taken to recover them. The characteristic volatile aroma that
responsible for the flavour profile of most freshly pressed juices
is present at levels typically around
only 700 parts per million and considerably less in heat treated
juices. In the
extraction of flavouring materials from the juicing process it is
no components of potential
value are wasted
and that the valuable non aqueous phase materials are collected. These
components are insoluble and form an unstable emulsion when applied to
Extraction and Use of Oil
is restricted to the
beverages and where necessary
(e.g. cola nut extract) specific methods of extraction
which result in
products compatible with aqueous and aqueous sugar
containing beverages in addition to beverages containing less than 20%
principal ingredient in all confectionery is sugar
(sucrose) which in its refined
form has little flavour
apart from its inherent sweetness. Raw (unrefined)
sugar has its own particular flavour. Other important carbohydrates
confectionery are corn syrup invert sugar and dextrose which are added
to control or prevent crystallisation. The texture of the confection
altered by their use and this property is used by confectioners to manufacture many varied
ingredients such as gums pectin gelatine starch milk
butter other fats and cocoa do most to give special textures although
not be forgotten that air
and water probably
have the greatest effect
in confectionery. Other ingredients which also play a part include
nuts coconut raw sugar (molasses) malt extract dried fruit fruit and
juices. These ingredients are added usually for their flavouring
for their contribution to the eating quality mouthfeel or nutritional
a confection. Some products owe their total appeal to these added
The flavour industry also provides extracts concentrates and
suit requirements for all these confectionery types.
and cooking (or heating) times also play an
important role in determining final taste and texture as they have a
significant effect on flavour and flavour develop ment.
1. shows temperature bands for producing various
confectionery types. The apparently large range is normal and takes
account recipe differences and texture required. Lower boiling
enable crystallisation to occur and a variation even as small as 0.5°C
a significant difference to the texture of most types of confectionery.
composition and procedures for the various types
are outlined but no account has been taken of water since it is used
dissolve sugar or other ingredients or to disperse gums. It is then
boiling or drying. The role of flavourings is also discussed.
Basic Confectionery Types, Recipes, Inherent Flavours
Boilings (Hard Candy)
a collective U.S. name for sugar confectionery whereas in the United
describes a special crystallised type.
natural colourings are used generally many times more
is dissolved in water and corn syrup added. The
mixture is boiled to the required temperature for example 147°C for a
sugar/corn syrup mix and cooled. Acid flavouring and colouring are then
and the resultant material moulded by various means to make the
confection. In large scale production liquid
syrup is metered into sugar solution and cooked in a microfilm cooker
called because a thin film of syrup is heated and brought to the
solids content under reduced pressure in the shortest possible time).
from being energy efficient no browning occurs and therefore little or
cooked flavour is apparent. This syrup is fed into a mixing chamber
calculated quantities of flavouring colouring and acid are added by
dosing pumps. The ingredients are then mixed and formed into a ribbon
cooling. The mass is finally transferred onto sizing rollers prior to
to a rope and moulding. On a small scale the batch is boiled in a pan
also have a facility to remove final amounts of water by vacuum. At the
temperature required the product is transferred to a cooling table
(confectioners slab which has the facility to have hot or cold water
through it) where the batch is cooled. When the correct temperature is
determined by the viscosity of the mass rather than any other factor
flavouring colouring and acid are added folded in and the confection
as before or passed through drop rollers. Drop here means the shape of
sweet (e.g. pear drops).
type of high boiling (candy) which should be
mentioned is the deposited type where the cooked flavoured acidified
coloured syrup is held at high temperature in special hoppers and
into metal moulds prior to cooling and wrapping. The acid used has to
buffered to prevent inversion of sugar whilst the colouring and
must be specially selected lo withstand the extra heating necessary.
sugar is produced by the addition of acid into the boil or by long slow
cooking. Excessive inversion leads to stickiness or even a product that
not solidify. While some confections
have invert sugar
added because it controls the crystallisation of super saturated
solutions it is usually added as commercially available material or as
syrup treacle or honey. Any additional
of invert sugar during cooking needs very careful control and buffer salts are added to
adjust the pH and
consequently the rate of inversion.
the same recipe pulled
sugar work (seaside rock figured
lollypops satins) can be made. Their manufacture necessitates pulling
previously boiled flavoured coloured and acidified sugar/corn syrup
a machine or over a hook to incorporate air. When moulding (to make
shapes or to build up letters) is complete the batch has to be kept hot
considerable time and this inevitably leads to deterioration of the
For this reason heat stable flavourings or lower quality products
topnotes which would be lost may be utilised. One way of introducing
flavours into boiled sugar is to prepare delicately flavoured centres.
pulps may be used to produce jams nut pastes may be prepared or whole
as well as all kinds of fillings based on chocolate. They are
the boiled sugar rope by means of a centre pump. The high boiled casing
protects and encloses the lower boiled portion enabling its finer
flavour to be
retained.Very many different confections are made using these same
ingredients some boiled to the higher temperature range (e.g. satins)
those boiled to lower temperatures are allowed to crystallise (e.g.
Looking at variations on
plain boiled sugar as described the addition
of fat is perhaps the most obvious. Traditionally this fat was butter
imparts a smooth mouthfeel excellent taste and is self emulsifying.
Butterscotch is made by the addition of 4% or more of butter solids and
flavour of this product is developed by exposing the raw materials to
temperature of manufacture.
method: Sugars and corn syrup are
dissolved and boiled together until a temperature of about 145°C is
Butter is then added and gently incorporated to preserve as much of its
as possible. The batch
is then boiled to the final
temperature of 145 160°C. Where higher temperatures
are preferred special arrangements for direct heating (gas) may
have to be made
since they are often too high for
steam heated equipment. The mass is then cooled and flavouring
the product is cut and wrapped. Generally lemon usually in the form of
oil is added since it is said to neutralise the greasy effect of fat.
flavourings are often used to enhance the character of
the product and
butter flavourings are popular too as they increase the overall buttery
Flavourings of commerce
intended for this
confection generally contain all these components in carefully balanced
on butterscotch recipes would be to alter the
proportion of white to brown sugar (or the replacement caramelised
are available). If the higher boiling temperatures are used to achieve
special cooked flavour and texture invert sugar has to be either added
during production in replacement for all or part of the corn syrup. The
inclusion of invert sugar in one
form or another results in
a much less viscous batch and higher temperatures are required to reach
same solids content. The amount of butter
may be varied or replaced totally or partially with other fats. Butter
natural emulsifying agents present so if other fats are used an
lecithin or glyceryl monostearate (GMS) has to be added in order to
proper dispersion of fat through the batch.
Incorporation of air either by means of pulling or the addition of frappe will result in Buttermint
types or Mintoes two
typical compositions are as follows.
of manufacture: Sugar syrup and corn syrup
are heated to about 130°C when butter (or other fats with emulsifiers)
added. The mass is reboiled to 138°C allowed to cool and peppermint oil
into the batch which is then pulled to the correct consistency spun
into a rope
formed and wrapped. Frappe is made by beating egg albumen (10%) or
(5%) into previously warmed corn syrup. Both these materials have to be
dispersed in minimal amounts of water before addition.
method: Sugar and corn syrups are
warmed to 140°C. Fat and lecithin are then added and when dispersed the
and peppermint oil are carefully stirred in. The mass is allowed to
finished as usual. The heat of the batch will expand air entrapped in
frappe and care must be taken to avoid its loss by excessive handling.
inconsistent batches it is necessary
to control the
temperatures used as well as manufacture of the frappe.
quality of peppermint oil used in this type of
product is important an oil
without harsh top notes will
enhance the smooth character of the confection. This may be a
natural American oil
(e.g. from Mentha piperita) or an oil
from China or Brazil (Mentha
arvensis) which will have been dementholised
at source and subsequently rectified to remove the harsher top notes
undesirable residues. Alternatively a mixture of the two may be used.
Most essential oil and flavour houses have suitable blends to offer. Butter flavourings may also
be added especially
when not all the fat used is butter. These are often made with a
background which accentuates the smooth character of the confection
with diacetyl and butyric acid. Both these substances are
present in butter and increasing the proportion of them boosts the
flavour considerably and replaces processing
losses. It should be noted they are available as both natural and
materials. Butter esters i.e.
from butter may also be used Composite flavourings based
on peppermint vanilla
and butter are also available.
products are in general based on three major ingredients and a number
of minor but
nevertheless extremely important components.
is in most cases the major ingredient and is
usually derived from wheat. It
may be whole wheat as in the
case of wholemeal flour or part of the wheat berry as in white flour.
It can be
of different grades depending on its protein content: high protein (11%
bread making and low (approx 9%) for cakes
and biscuits. In addition flour can be treated in various ways to
amount of damaged starch cells a factor which in turn increases its
power. It is also possible to treat flour
with oxidising agents (typically ascorbic acid) either to
apparent strength of the protein fraction or
as is the case in the Chorleywood Breadmaking Process to reduce the
required for fermentation when used in conjunction with mechanical
It is also a requirement in law that white flour is nutritionally
with calcium and iron plus vitamins. None of these processes have
likely to. cause major flavour problems. Anyone interested in understanding more about
flour and its properties
should read Modern Cereal Chemistry
or some of the other
major works on the subject.
are of course other cereals that can be used rye oats
and maize being the
most common. Rye is of particular
interest in that it was normal in continental practice to produce a rye
a long period of fermentation which gives the product a particular
helps to improve keeping properties of the bread. It is possible to
this effect and its shelf life improvement
by the use of flavourings and chemical additions. By this means the
inherent in long fermentation periods of the culture of undesirable
microbiological organisms is avoided. The practice of sour dough
systems is now
little used as it is being replaced by
flavourings or specially prepared dried sours made under strictly
are the second major ingredient to be found in
most bakery formulae. There are many different sugars that can be used.
is the most common both in granular form or as a
ground powder it is also available in its partly refined stage as brown
best known of which is probably demerara.
or its partly refined stage golden syrup is
another sweetening ingredient manufactured as a by product of sugar
it is used not only for its sweetening property but as a flavouring in
is produced by the acid or enzymic conversion
of starch derived from maize or as a by product of protein extraction
wheat flour. It is typically available either
as a component of liquid glucose syrup or as a powder (dextrose
syrup is supplied
with different levels of
conversion of starch to sugars which is measured as dextrose equivalent
The syrup is sold within a range of solids (72 84%) depending on its
sugar is a product of acid or enzyme treatment in
this case the substrate is sucrose. It has many properties similar to
and is often used in formulae for its ability to act as a humectant. We
also consider honey in this group it is used as a flavouring ingredient
as a sweetener. There are many honey types all of which have different
characterised by the flowers visited by the bee at the time the honey
bulk sweeteners fructose and polyols such as
sorbitol are used to make products suitable for diabetics as they do
require the human digestive system to provide insulin.
are the third major ingredient. They are derived from animal and vegetable sources and have
to undergo several
purification steps before being suitable for bakery use. The processes
filtration colour and flavour removal fractionation and hydrogenation
manufacturer to produce tailor made fats for the particular
very special flavour characteristics of butter that are changed during
baking process must also be considered. These are the target of much
in the flavour industry the results of which have produced some
flavourings which can add a special note to many baked products.
are one of the minor but very important ingredients in bakery formulations and are
normally added in one or
more of many forms including egg milk
and water. The
prime function of liquid
to bind all the various additions of the formulae holding
in the early stages of the baking
Later as the temperature rises a secondary function of the protein
egg coagulates to produce structure. Free liquid then enters the
grain of the flour and allows gelatinisation to take place again adding to the structure of
the product. The
retention of moisture in the finished item is important in its taste
when eaten. Lack of moisture can for example make a cake unacceptable
too much of it can make a biscuit equally unpleasant to eat.
producing the effect of aeration are another minor but important ingredient.
aeration although not strictly an added ingredient can be produced by beating or
whisking and here egg has
a very important role in baked products in that it can hold air in its
structure. Fat of the correct type will entrap air when beaten.
also be produced by chemical and biochemical components.
aeration is possible using ammonium carbonate which
on heating decomposes to produce ammonia carbon dioxide and water.
Unfortunately ammonia tends to re dissolve into any available water in
product and is therefore not acceptable in high moisture products such
It does form a very useful aerating ingredient for biscuits and low
items. Sodium bicarbonate
upon heating will release
some carbon dioxide however the reaction can be made to produce more
dioxide when used in conjunction
variety of acids. Although chemical residues remain after both
they are considered acceptable tastes in powder aerated products. The common acids
delta lactone is preferred in that it produces
the minimum after taste. Biochemical aeration by the use of yeast
specially cultivated variety (Saccharomyces cerevisiae) is
source of biochemical aeration although it is possible to take
advantage of the
yeast spores floating in the air or found on the surface of fruits.
obvious risks in using these so called wild yeasts as they can be a
unreliable source of aeration and so are little used.
breaks down the available carbohydrates by the use
of enzymes in a fermentation process which produces carbon dioxide gas
large range of other organic chemicals including ethyl alcohol pyruvic
acetaldehyde some of which can then go on to further reactions. Many of
chemicals produced have flavour and it is this complex combination
bread its unique taste.
hear that you are experts in dairy flavourings. Well I
need a cheese flavouring of general Cheddar type with a hint of Blue a
buttery creamy background and perhaps a slight Swiss fruitiness. I want
it in a low fat cheese sauce for a low calorie fish and pasta frozen
designed for both microwave and conventional oven preparation. The
must be a powder with no added flavour enhancers like monosodium
it cannot be artificial in fact the Marketing Department would prefer
it to be
totally natural. And by the way the finished product is to be sold
Europe and Scandinavia.
above transcript of a hypothetical call from a
development technologist in a food company is sadly not as typical as
flavourist might hope. All too often the flavour requirements are much
tangibly defined the end product and processing are not revealed and
and marketing implications of the target market are not clear. This
job of the flavourist trying to satisfy customers flavour needs much
difficult. It is very important that the flavourist engages the
dialogue about his or her flavour needs. Only then can the flavourist
experience to help to satisfy those needs.
basic areas of knowledge which the experienced dairy flavourist draws
understand and fulfil the flavour needs of today s demanding food
technologist. It has been written mainly for the flavourist venturing
dairy flavour types for the first time but should prove of interest to
interested in other flavourists views. It is not highly technical but
basics which help to build up a feel for dairy flavours.
may be surprised by the breadth of information about
different types of real cheeses butters and other dairy products. Such
understanding is vital to the process of defining the flavour target
target must be adequately defined if you are to have any chance of
the flavour in a processed food product.
All dairy products start
out as milk their flavour components tend to
be similar the secret of their varied and unique characters is in the
of those components.
Milks as a Human Food Source
The earliest domestication
of animals is believed to have been about
6500 BC and with this came the widespread consumption of animal milks
It is highly likely that the practice had begun long before this time
milk of wild animals hunted for their flesh. The nature of milk itself
influence of weather probably gave rapid rise to a range of dairy
this formed the basis of the wide range of milk products we have come
today. We should be grateful that early man discovered the variety of
dairy products before he devised refrigeration a process which might
prevented many of them from developing!
Flavour in Dairy Products
there are significant species variations animal
milks are generally oil in water emulsions containing varying
triglyceride fats with the characteristic milk protein casein (plus
proteins at much lower levels) the milk sugar lactose and a broad range
vitamins and minerals. In short they contain just the necessary mix of
nutrients to ensure the healthy development of the juvenile of the
until it is able to digest other foods.
macroscopic components are not solely responsible
for the varied flavours we associate with dairy products. They provide
materials for the development of an immense variety of aromatic
the protein lactose and fat
components directly yields many aroma compounds
some more desirable than others! But the great variety in dairy product
flavours would not occur without the action of a range of
selectively act on the raw milk to give compounds responsible for the
flavour characters. Further chemical interaction between these
increases the range of chemical species which contribute to dairy
between the milks of different species manifest
themselves mainly as differences in lactose protein and fat levels and
in differences in the chemical composition of the fat triglycerides.
turn gives rise to differences in the types and balance of small
molecules liberated in degradation processes. Thus there is significant
variation in flavour between dairy products derived from milk of
species despite the broadly similar reactions taking place.
in many areas of flavour science understanding of
dairy product flavours has advanced tremendously in the last 30 years.
been largely driven by the increasing availability of instrumental
techniques which allow detailed examination of the low level components
complex mixtures. Gas
mass spectrometry have revolutionised the study of all
flavours and of dairy flavour in particular. Together these two
separation and identification of components in extracts from dairy
However they do not indicate which components are the most important contributors to
the overall flavour of
the dairy product. For this the trained human nose is still the most
not the only means of analysis. Sometimes the nose can usefully be used
aroma specific detector for the gas chromatograph indicating which
should be further studied by mass spectrometry and other techniques.
can be a list of the key compounds which together
flavour of the product under study.
But even this is of
to the flavourist unless the compounds are available or could be made
within commercial cost restraints. So although analytical information
great help the skill and experience of the flavourist
in the development of commercially viable flavourings.
Uses of Dairy Flavourings
flavourings are used throughout almost all sectors
of the manufacturing food industry from snack foods through to
beverages from sugar confectionery to ready meals from dairy products
specifically non dairy foods. The range is extremely wide and this
certain approach from the
It is vital to obtain as
much information as possible about the application the customer has in
a minimum each of the following considerations should be addressed.
flavourist must be a jack of all trades expert in whatever discipline
Intermittently and concurrently the
skills of chemist artist food technologist designer marketeer consumer
psychoanalyst may be needed in order to identify and satisfy the
needs. The customer has an idea of what he wants the
department sets a brief the food technologists
research the practicalities. Ideally the flavourist works alongside
process to achieve the desired flavour profile.
can obviously benefit from a detailed
knowledge of the compounds responsible for flavour in real dairy
this is only a part of the story. The inherent flavour of the product
greatly affect the emphasis of the required flavouring. Many of the
of the real thing will be technically unavailable or commercially
flavour of the real thing may not even be what the customer really
Before commencing development work on any project flavourists should
themselves that they fully understand the customer s needs. The best
way to do
this is to question the customer directly. Such a direct approach is
rejected as most food product developers realise this is the most
for them to achieve their goals.