Perfumes
MARC VOM ENDE, Symrise AG, Holzminden, Germany
WOLFGANG STURM, Haarmann & Reimer GmbH, Holzminden, Germany
KLAUS PETERS, Haarmann & Reimer GmbH, Holzminden, Germany
1. Introduction . . . . . . . . . . . . . . . .
2. Raw Materials and Production. . .
3. Perfume Compositions . . . . . . . . .
4. Development of Extrait Perfumes .
4.1. Fragrance Concepts (Fragrance
Families) . . . . . . . . . . . . . . . . . . .
4.2. Fragrance Notes . . . . . . . . . . . . .
1. Introduction
Although perfumes are alcoholicaqueous solu-
tions of perfume oils, the term perfume is also
used to denote concentrated perfume oil. Per-
fume oils may be composed of natural products,
synthetic fragrance substances, or a combina-
tion of both. We mainly nd a combination of
natural and synthetic fragrance substances in
perfumes. The art of perfumery consists of
combining a wide range of raw materials to
create a harmonious, pleasant, and expressive
fragrance which transports or supports a certain
idea or statement.
History. Mixtures of fragrance substances
(odorants) in the form of incense (Latin perfu-
mum) and perfumed unguents were used for
ceremonial purposes in early times. Archeologi-
cal excavations in Cyprus give the earliest evi-
dence of a perfume factory. The industrial
perfume complex dates back to the second mil-
lennium BC. The typology of vessels and mate-
rials found proves the use of three methods to
obtain odorants: Boiling of barks, distillation,
and maceration in olive oil and water. Along
with their ritual uses, perfumes became important
among the Greeks and Romans as luxury items.
After the isolation of essential oils from plant
parts, the art of perfumery advanced rapidly.
French perfumery has held a dominant position
in Europe since the reign of Louis XII (ca. 1500).
2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
10.1002/14356007.a19_171.pub2
. . . 1 5. Perfumes for Cosmetics, Toiletries, and
. . . 2 Household Products . . . . . . . . . . . . . . 6
. . . 3 6. Environmental and Safety Aspects . . . 7
. . . 5 7. Economic Aspects . . . . . . . . . . . . . . . 7
References. . . . . . . . . . . . . . . . . . . . . 7
... 5
... 6
Around 1700, GIOVANNI PAOLO FEMINIS, an
Italian who had migrated to Cologne, began
marketing what later became eau de cologne.
The classic formula for this product consists of
bergamot oil, lemon oil, orange oil, and orange
ower oil in ethanol. The original name aqua
mirabilis (marvelous water) was replaced by
aqua coloniensis and Klnisch Wasser (Colonia
is the Latin name of the city of Cologne, and
Kln is its German name), and nally, by eau de
cologne. Several rms in the city, including
Johann Maria Farina and 4711, made eau de
cologne a world-famous product.
In the 19th century, the German company
Schimmel in Leipzig made a lot of progress in
perfumery. Schimmel published reports in vari-
ous languages on crops of natural perfumery
materials and on analytical methodologies. Due
to the novel way of open information, knowl-
edge in perfumery advanced rapidly. Modern
perfumery began at the end of the 19th century
when the rst synthetic fragrance materials were
used in perfumes (e.g., Fougre Royale from
Houbigant, 1882, using coumarin; Jicky from
Guerlain, 1889, using ethylvanillin). The impor-
tance of perfumery has increased greatly since
then. It includes not only ne products (perfume
and eau de cologne), but also the use of per-
fumes in cosmetics, toiletries, soaps, and house-
hold or industrial products.
In addition to French perfumery, North Amer-
ican perfumery has become very important since
2 Perfumes
the 1960s. With respect to distinctive fragrance
types as well as market volume, both now enjoy a
virtually equal status. The perfumery markets in
different regions are very strong varying in their
preferences to certain odor proles. This also
depends on the cultural background in those
regions.
2. Raw Materials and Production
The raw materials used in perfumery are essen-
tial oils, extracts from plants, fragrance sub-
stances isolated from products of natural
origin, purely synthetic aroma molecules, and
synthetic aroma molecules-based products of
natural origin. The number of natural fragrance
substances are limited, but the increasing rene-
ment of analytical techniques continues to yield
new and interesting natural products. Chemical
synthesis is, however, mainly responsible for
the steady stream of innovations in perfumery
since the turn of the 20th century.
The production and properties of aroma
chemicals and fragrance substances are described
in [1].
Raw Materials of Plant Origin. The following
products are isolated from plant raw materials:
1. Essential oils, obtained by pressing plant
materials or by steam distillation
2. Concretes, obtained by extraction with vola-
tile solvents, such as diethyl ether, benzene
derivatives, or alcohols
3. Resinoids, produced by extraction of aro-
matic resins, mosses, balsams, and roots
with volatile solvents
4. Absolutes, derived by treating concretes and
resinoids with ethanol
The starting materials for these products are:
Flowers, such as rose, jasmine, lavender,
and neroli (orange ower)
Stalks and leaves, such as geranium,
patchouli, and petitgrain
Fruits, such as anise, coriander, caraway,
cumin, and juniper
Peel of citrus fruits, such as bergamot,
lemon, and orange
Seeds, such as mace, angelica, celery, and
cardamom
Roots, such as angelica, vetiver, and iris
Woods such as sandalwood, cedar, and
guaiac
Herbs and grasses, such as tarragon, lem-
ongrass, sage, and thyme
Needles and twigs of spruce, r, rosemary,
and pine
Resins and balsams, such as those derived
from galbanum, elemi, benzoin, myrrh,
and olibanum
Both the natural products and the aroma
chemicals isolated from them are employed in
perfumery. Examples of the latter are geraniol
and citronellal from citronella oil, citral from
lemongrass or Litsea cubeba oil, eugenol from
clove oil, and menthol from peppermint oil.
Raw Materials of Animal Origin. In perfum-
ery production, raw materials of animal origin
are not any longer in use. This is due to animal
protection and legislation. The following had
been used:
Ambergris, a metabolic product excreted
by sperm whales that may result from a
pathological condition
Musk, a glandular secretion of a hornless
deer of Central Asia
Civet, a glandular secretion of the civet cat
Castoreum, a glandular secretion of the
beaver
Beeswax, produced by bees
Semisynthetic and Synthetic Aroma Chemi-
cals. Semisynthetic products are obtained by
chemical modication of a natural starting mate-
rial. They include hydroxycitronellal from cit-
ronellal, citronellol from geraniol or citronellal,
geranyl acetate from geraniol, and ionones and
methylionones from citral.
Purely synthetic fragrance substances are
produced from basic chemicals by complete
synthesis. They can be divided into products
that are identical to natural ones and products
that do not occur in nature. Products identical to
natural substances but obtained by chemical
synthesis include benzyl acetate from toluene,
phenethyl alcohol from benzene, menthol from

thymol, and linalool, a product of acetylene
synthesis.
Other synthetic aroma chemicals have
molecular structures that do not occur in nature.
They can be produced only by chemical syn-
thesis. They often imitate the olfactory impres-
sions of natural raw materials. Examples are 4-
tert-butylcyclohexyl acetate (woody note, violet
note), -amylcinnamaldehyde (jasmine), and
ethylene brassylate (musk).
Many natural products continue to be indis-
pensable in perfumery. However, synthetic
products play an increasingly important role
in the perfumers assortment of raw materials
because of their virtually unrestricted availabil-
ity, constant quality, and distinctive olfactive
expression in a perfume. Modern analytical
techniques allow identication of the compo-
nents of natural mixtures, which are often very
complex. Reconstitution of these products and
of essential oils by synthetic materials has led to
substitutes with olfactory distinction.
Fixatives are used to equalize the vapor pres-
sures and thus the volatilities of the raw materi-
als in a perfume oil as well as to increase the
tenacity.
Natural xatives are resinoids (benzoin, lab-
danum, myrrh, olibanum, storax, and tolu bal-
sam). Synthetic xatives include substances of
low volatility (cyclopentadecanolide, ambrox-
ide, benzyl salicylate) and virtually odorless
solvents with very low vapor pressures (benzyl
benzoate, triethyl citrate).
Solvents. The only solvent used in ne perfum-
ery is extremely pure ethanol that is diluted with
water to the required concentration. Weakly
odorous synthetic xatives are used as solvents
for alcohol-free perfumes, especially bazaar
oils. (Bazaar oils are perfume oils that are
dissolved in an oily solvent; they are sold in
bazaars in Arabian countries and used as
perfumes.)
Production. Perfumes were originally pre-
pared from alcoholic infusions, solutions,
and tinctures of oral extracts, essential oils,
natural and articial aroma chemicals, drugs,
and resins. The long storage times allowed
complete clarication and maturing of the
alcoholic solutions, so that the perfumes
required a much shorter aging time. As a result
Perfumes 3
of increasing industrialization, perfumery has
departed from these classical methods of prep-
aration. Today, perfume compositions pre-
pared in the form of perfume oils are
dissolved in ethanol, cooled to ca. 0C, ltered,
packaged, and marketed. Perfume (extrait) may
be, for example, a 1020 vol% solution of a
perfume oil in ca. 9095 vol% ethanol. An eau
de toilette or eau de parfum contains ca. 710
vol% perfume oil in 8090 vol% ethanol; an
eau de cologne up to 4 vol% perfume oil in ca.
7085 vol% ethanol.
3. Perfume Compositions
In building up a composition, the perfumer must
work systematically and observe certain rules of
workmanship. A fragrance can be divided into
three parts:
1. Top note or initial fragrance impression
2. Heart note or middle note
3. Base note, dry out, or end note
The odor must pass smoothly from one phase
to the next; the overall character of the perfume
should be clearly perceptible from the top note
to the end note.
Linear Compounding. A sample formula is
described to illustrate the formulation of a oral
fragrance. This formula also demonstrates the
technique of linear composition, which is based
primarily on well-dened aroma chemicals and
essential oils. Complex compounding, on the
other hand, mainly uses predesigned and bal-
anced perfume bases and fragrance complexes.
Sample Formula. The fragrance materials in
the oral bouquet (Table 1) correspond to a
variety of owers; they give a basic, inherently
rounded oral complex. Nuancing agents for the
top note are fresh-citrus components, such as
bergamot oil and lemon oil, whereas several
powdery, woody and musk odorants, such as
ethylene brassylate and ambroxide serve as
xatives.
Complex Compounding. In complex com-
pounding, separately balanced perfume bases
are used instead of individual fragrance materi-
als or fragrance accords. These bases consist of
4 Perfumes

Table 1. Floral bouquet

Composition Olfactive impression Compound Quantity, g

Top note bergamot oil 20

orange oil 10
lemon oil 20
pink pepper extract 2
ozone orazon 10% 5
Floral complex rose phenethyl alcohol 100
rose geraniol 20
rose citronellol 60
lily of the valley orosa 100
lily of the valley bourgeonal 1
lily of the valley vertomugal 10% 2
jasmine hedione 284
gardenia magnolan 80
cyclamen calone 10% 5
Fixation powdery vanillin 5
powdery cinnamic alcohol 5
apricot decalactone gamma 1
cedarwood Iso E Super 130
ambergris ambroxide 5
musk globalide 50
musk globanone 10
musk ethylene brassylate 85
1000

numerous components; appropriate mixtures of Table 2. Rose base

synthetic products are also substituted for the
Composition Compound Quantity, g
fragrance complexes of natural essential oils.
The complex method yields a more well- Top note aldehyde C9 0.5
aldehyde C10 0.5
rounded composition than several individual aldehyde C11 undecylenic 0.5
fragrance materials, but it has the risk of ending Heart phenethyl alcohol 438.5
in a stew-like composition with no distinctive phenethyl acetate 50
expression. phenethyl isobutyrate 5
geraniol 100
Another reason for the existence of bases is citronellol 200
a way of promoting certain perfume raw geranyl acetate 5
materials, such as specialties or captives. Spe- benzyl salicylate 20
cialties are raw materials that are mainly vertomugal 20
hexyl cinnamaldehyde 20
provided by one perfume raw material pro- eugenol 5
ducer. Captives are perfume raw materials that benzophenone 15
only one perfume house produces. Within dimethyl benzyl carbinyl acetate 40
bases those materials are combined to give Fixation phenethyl phenylacetate 50
cinnamic alcohol 30
distinctive olfactive impressions [2]. 1000
As positive example the simple rose accord
in the oral bouquet (Table 1), consisting of
citronellol, geraniol, and phenethyl alcohol, can
be replaced by a rose base (Table 2) whose complex makeup and a very rounded odor. A
composition has been worked out in much more balance has been found between linear and
detail. complex composition in perfumery production
Replacement of fragrance notes composed of since the end of the 20th century. Reasons are
a few substances, as described in Table 1, by more complexity regarding different require-
sophisticated perfume bases of appropriate odor ments to several customer restrictions and
type yields a composition consisting of several cost-related issues to perfume production and
hundred components that has an exceedingly stock holding.

4. Development of Extrait Perfumes
4.1. Fragrance Concepts (Fragrance
Families)
Extrait perfumes set the trends for all develop-
ments in perfumery. They are important for any
creative perfumer, regardless of the application
for which new fragrance compositions are devel-
oped. The many perfumes on the market can be
classied according to different classications.
The existing classications emphasize on differ-
ent aspects of the landscape of perfumes. A very
widely used classication is the genealogy of
perfumes. The idea of seeing the development in
perfumery as a kind of evolution goes back to
ROBERT R. CALKIN, perfumer and former botanist,
who openly spread the idea of the perfume
genealogy in the 1960s also within the British
Society of Perfumers [3]. The rst published
genealogy by Haarmann & Reimer has since
then been adjusted to the need of the developing
landscape of perfumes. The many perfumes on
the market today can be classied according to
nine main perfume concepts or perfume families
(the system is opened to future changes due to
new upcoming perfume concepts and trends):
1. Floral concept (Floral Family)
a. Characteristic raw materials:
Benzyl acetate (jasmine), hedione (jas-
mine), jasmine absolute (jasmine), ter-
pineol (lilac), anisaldehyde (lilac),
phenethyl alcohol (rose), geraniol
(rose), citronellol (rose), hydroxycitro-
nellal (lily of the valley), ionones (iris,
violet), methyl octine carbonate (vio-
let), eugenol (clove), clove oil (clove)
b. Typical products:
N5 (Chanel, 1921); Joy (Patou, 1935);
LAir du Temps (Ricci, 1948); Fidji
(Laroche, 1966); Giorgio (Beverly Hills,
1981); Poison (Dior, 1985); Fahrenheit
(Dior, 1988); LEau dIssey (I. Miyake,
1991); Be Delicious (D. Karan, 2004)
2. Oriental Concept (Oriental Family)
a. Characteristic raw materials:
Vanillin, ethylvanillin, coumarin, tonka
bean extract, benzoin extract, Peru bal-
sam oil, and musk aroma chemicals like
globalide, ethylene brassylate
Perfumes 5
b. Typical products:
Shalimar (Guerlain, 1925); Youth
Dew (Lauder, 1952); Obsession for
Men (C. Klein, 1986); Tom Ford
Noir (T. Ford, 2012)
3. Chypre Concept (Chypre Family)
a. Characteristic raw materials:
Combination of bergamot oil, cistus
labdanum, and oakmoss notes with
patchouli oil
b. Typical products:
Chypre (Coty, 1917); Miss Dior (Dior,
1947); Ysatis (Givenchy, 1984);
Angel (Mugler, 1991); Coco Made-
moiselle (Chanel, 2001); Narcisso
Rodriguez for him (Narcisso Rodri-
guez, 2007)
4. Floriental Concept (Floriental Family)
a. Characteristic raw materials:
Combination of a dominant oral
accord with powdery and ambergris
notes like vanillin, ambroxid,
ketamber
b. Typical products:
Poison (Dior, 1985); Hypnse (Lan-
cme, 2005); Kenzo Amour (Kenzo,
2006); Victorias Secret Night (Victo-
rias Secret, 2013)
5. Citrus Concept (Citrus Family)
a. Characteristic raw materials:
Combination of citrus raw materials,
which are dominant in the perfume,
such as lemon oil, bergamot oil,
orange oil
b. Typical products:
4711 (Muelhens, 1792); Eau Sauvage
(Dior, 1966); Cologne (Mugler, 2001);
Lengling N5 Eisbach (Lengling,
2015)
6. Green Concept (Green Family)
a. Characteristic raw materials:
Aroma molecules or natural products
which give the impression of green
(e.g., cis-3-hexenol, galbanum oil)
dominating in combination with oral
notes
b. Typical products:
Vent Vert (Balmain, 1947); LEau de
Campagne (Sisley, 1976); Truth (Cal-
vin Klein, 2000)
6 Perfumes
7. Fruity Concept (Fruity Family)
a. Characteristic raw materials:
Aroma molecules with fruity im-
pression like gamma-undecalactone
(aldehyde C14 (so-called)), or ethyl
methylphenylglycidate (aldehyde C16
(so-called)), frambinon or melonal in
combination with oral notes
b. Typical products:
Calyx (Clinique, 1986); Ralph (Ralph
Lauren, 2000); Victorias Secret Scan-
dalous (Victorias Secret, 2014)
8. Woody Concept (Woody Family)
a. Characteristic raw materials:
Natural products like cedarwood oil,
sandalwood oil, or woody aroma mol-
ecules like Iso E Super, cashmeran,
ambrocenide are dominant in the
perfume
b. Typical products:
Vetiver (Guerlain, 1966); Fminit du
Bois (Shiseido, 1992); Alien (Mugler,
2005); Terre dHerms (Herms, 2006)
9. Fougre Concept (Fougre Family)
a. Characteristic raw materials:
A combination of bergamot notes, lav-
ender oil, coumarin, and evernyl as a
mossy note.
b. Typical products:
Fougre Royale (Houbigant, 1882);
Cool Water (Davidoff, 1988); Le
Mle (J. P. Gaultier, 1995); Bleu de
Chanel (Chanel, 2010)
4.2. Fragrance Notes
Within each fragrance concept, individual fra-
grance notes can give a specic twist. Examples
follow:
1. Aldehydic Note
a. Characteristic raw materials:
Aliphatic aldehydes (C6C14)
b. Typical products:
Chanel N5 (Chanel, 1921); Essence
Narciso Rodriguez (Narciso Rodri-
guez, 2009)
2. Spicy Note
a. Characteristic raw materials:
Clove oil, eugenol, pimento berry oil,
cinnamon oil, nutmeg oil
b. Typical products:
LAir du Temps (Nina Ricci, 1948);
Opium (Yves Saint-Laurent, 1977);
Fminit du Bois (Shiseido, 1992)
3. Musky Note
a. Characteristic raw materials:
Ethylene brassylate, globalide, globa-
none, muscone
b. Typical products:
Eau parfume au th vert (Bulgari,
1993); CK BE (Calvin Klein, 1996);
Cologne (Thierry Mugler, 2001); Voy-
age DHerms (Herms, 2010)
4. Edible Note
a. Characteristic raw materials:
Ethyl maltol, maltol.
b. Typical products:
Angel (Mugler, 1992); Flowerbomb
(Viktor&Rolf, 2005); La Petite Robe
Noir (Guerlain, 2009); Loverdose
(Diesel, 2011)
5. Perfumes for Cosmetics,
Toiletries, and Household Products
Perfumes and eau de cologne are used speci-
cally for their odor. In cosmetics, toiletries, and
household products, the perfume is usually of
secondary importance for the effectiveness of
the product; it may, however, strongly inuence
the consumers decision to buy a product and, in
many cases, represents the only way of making
the products action perceptible to the
consumer.
Although the model fragrance types are often
created from the eld of ne perfumery, chemi-
cal and physical aspects must also be taken into
account in the development of perfume oils for
toiletries and household products. For example,
the perfume oil used in creams and white soaps
must not cause discoloration; a perfume oil for
aftershave lotion must be soluble in 5060%
alcohol; the fragrance used in a powdered deter-
gent must be alkali resistant; a fabric softener is
expected to leave clothes with a pleasant
odor; even a household cleanser must have a
pleasant but functional odor, although active
chlorine places extraordinary demands on the
stability of the perfume oil. Minimal perfume
doses are expected to adequately mask the often

strong and unpleasant odors of products, such
as insecticides, oor cleanser, paints, and
varnishes.
Soaps are of less importance nowadays in
Europe and North America. They are still very
important on the African continent. The fra-
grances must satisfy the following require-
ments: Chemical resistance, low volatility of
raw materials (e.g., geraniol and ionone),
strength of odor in soap (e.g., citronellal), and
adhesion to the skin (e.g., -amylcinnamic alde-
hyde). In the past, well-dened perfume types,
such as lavender, citronella, rose, lilac, pine, and
fern (fougre) were preferred. Today, however,
perfumes are custom formulated, usually in
fantasy notes mainly oriented to ne fragrances,
personal care, and cosmetics.
Olfactory enhancement of all types of
household products has become increasingly
important since the 1980s. The development
of perfume oils for this wide-ranging eld
requires a special knowledge of perfumery, as
well as information about the chemical and
thermal stability of the perfumery materials
used and their impact and substantivity in rela-
tion to the product being perfumed. [Substan-
tivity denotes the afnity of a perfume material
for a substrate, e.g., bers (fabric conditioners)
or hair (hair conditioners).]
6. Environmental and Safety
Aspects
The usage and creation of perfumes is seen in
respect to environmental and safety aspect.
Certain materials are limited or banned by
law. For more details see [4]. Many producers
of products that contain perfume have their own
specic regulatory guidelines. All those regula-
tions have a strong impact on creation of per-
fumes in respect of the olfactive expression of
fragrances.
7. Economic Aspects
The world market size of fragrances was
approximately 10.1 109 in 2016. The split
Perfumes 7
between different categories in Euros is as
follows:
Fine perfumes 1.6 109, personal care 3.0
10 , laundry 3.2 109, home care 1.8 109,
9
other fragrances 0.5 109.
The split of all fragrances sold (in ) in
regions in 2016 is as follows:
Europe, Africa & Middle East 2.9 109,
North America w/o Mexico 2.4 109, Latin
America 1.1 109, Asia Pacic 3.7 109 [5].
References
1 Surburg, H. and Panten, J. (2016) Common Fragrance and
Flavor Materials, 6th edn, Wiley-VCH, Weinheim.
2 Robert, R. and Calkin, J. (1994) Stephan Jellinek: Perfumery
Practice and Principles, Wiley-Interscience, New York, p. 94.
3 Robert, R. and Calkin, J. (1994) Stephan Jellinek: Perfumery
Practice and Principles, Wiley-Interscience, New York,
pp. 101106.
4 Surburg, H. and Panten, J. (2016) Common Fragrance and
Flavor Materials, 6th edn, Wiley-VCH, Weinheim, p. 268.
5 IAL Report (2016) 10th edn.
Further Reading
van Toller, S. and Dodd, G.H. (1989) Perfumery, the Psychology and
Biology of Fragrances, Chapman and Hall, London.
Ohloff, G. (1990) Riechstoffe und Geruchssinn, Springer Verlag,
Heidelberg.
Haarmann & Reimer (1984) The H + R Book of Perfume, Johnson
Publications, London.
Jellinek, C. (1949) Praktikum des modernen Parfumeurs, Urban &
Schwarzenberg, Wien.
Jellinek, C. (1951) Die Psychologischen Grundlagen der Parfm-
erie, Hthig Verlag, Heidelberg.
Jellinek, J.S. (1976) Parfmerien von Produkten, Hthig Verlag,
Heidelberg.
Wrner, P. (1985) Genealogie der Extrait-Parfums, Haarmann &
Reimer, Holzminden.
Dorland, W.E. and Rogers J Jr., J.A. (1977) The Fragrance and Flavor
Industry, Wayne E. Dorland Comp., Mendham, New Jersey.
Berger, R.G. (2007) Flavours and Fragrances, Springer, Berlin.
Perring, K.D. (2016) Perfumes, Kirk-Othmer Encyclopedia of
Chemical Technology, John Wiley & Sons, Hoboken, NJ, pp.
146. online doi: 10.1002/0471238961.1605180619030818.
a01.pub3.
Schreiber, W.L. (2005) Perfumes, Kirk Othmer Encyclopedia of
Chemical Technology, 5th edn, John Wiley & Sons, Hoboken,
NJ. online doi: 10.1002/0471238961.1605180619030818.a01
.pub2.
Sell, C. (2006) The Chemistry of Fragrances, 2nd edn, RSC Pub-
lishing, Cambridge.
Lentini, A. (2007) Sostanze odorose e terapeutiche dal sito preis-
torico di Pyrgos-Mavroraki, in I profumi di Afrodite e il segreto
dellolio, pp. 89109 Gangemi, Roma.
Wellmann, M. (1958) Pedanii Discoridis. De Materia Medica I,
Weidmann Verlag, Berlin.