The Art & Science of Fragrance & Flavor Creation: December 2003

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The Art & Science of Fragrance & Flavor Creation
Conference Paper · December 2003

DOI: 10.13140/2.1.3076.5123
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The Art & Science of
Fragrance & Flavor Creation
John C. Leffingwell
Society of Flavor Chemist’s

December 4, 2003
Fragrance & Flavor – Art & Science
 Conventional Market View – U.S. $15 Billion
Worldwide Market
Flavors vs. Fragrances
Flavors Fragrances
49% 51%
Western North
Europe America
25% 32%
Eastern
Europe
5%
Middle East & Asia-Pacific

South America
Africa 26% 6%
6%
Flavor & Fragance Market excluding
Branded Soft Drink Concentrates
12% - International
Danisco - 1.7% (DK)
Flavors & Fragrances
(US)
12.8% - Givaudan (CH)

Others - 35.4%
7.6% - Quest Int'l (NL)
Sensient - 2.8% (US)

9.1% - Firm enich (CH)
T. Hasegaaw a - 2.5 %
(JP)
8.6% - Sym rise (DE)
Mane - 1.8% (FR)
Takasago - 5.6% (JP)
 The Real Market – U.S. $30 Billion
Flavor & Fragrance Market
Including Branded Soft Drink Concentrates
Other Branded Soft Drinks
Cadbury Schweppes
3% 3%
16%
Pepsico
39%
Flavor &
Fragrance
Coca-Cola
39%
 Fragrance & Flavor - The shaping of history
 Prehistory - Culinary & Fragrant Oils

Earliest items of commerce were most likely
spices, gums and other fragrant plants.
 Circa 7000 BC – Fragrant plants and spices

infused in the fatty oils of Olive & Sesame for use
as ointments
 The shaping of history
 3000 BC – Indus Valley (Pakistan) - terra-cotta

perfume containers and a primitive still - place it
3,000 years earlier than most sources date the
invention of distillation.
 3000 BC – Egyptians– when learning to write and

make bricks, were already importing large
quantities of myrrh.
 The shaping of history - Egypt
Perfume Vessel Symbolizing Unification - Reign of

Tutankhamon
Calcite pots filled with spices such as frankincense preserved
in fat still gave off a faint odor when opened in King
Tutankhamen's tomb after 3,000 years
 The shaping of history – Greece
Greek Perfume Urns

By the 7th century BC, Athens had developed into a mercantile
center in which hundreds of perfumers set up shop. Trade was
heavy in fragrant herbs such as marjoram, lily, thyme, sage,
anise, rose and iris, infused into olive, almond, castor and
linseed oils to make thick unguents. These were sold in small,
elaborately decorated ceramic pots, similar to the small jars
still sold in Athens today.
 The shaping of history – Greece circa 400 BC
Still of Democritus
Leucippus and Democritus – Fathers of the Atomic
Theory
The first firm documentary evidence of the
distillation of essential oils is Herodotus' record
of the method of distilling turpentine from 425 B.C.
 The shaping of history – Perfume basics - 300 BC
 Socrates’ classmate, Theophrastus, sent plant

cuttings obtained during his extensive travels, thus
establishing a botanical garden in Athens.
 Theophrastus' treatise “On Odors” covered all the

basics: blending perfumes, shelf life, using wine
with aromatics, substances that carry scent, and
the effect of odor on the mind and body.
 The shaping of history – International Trade
 As trade routes expanded, Africa, South Arabia and

India began to supply spikenard and ginger to
Middle Eastern and Mediterranean civilization.
Phoenician merchants traded in Chinese camphor
and Indian cinnamon, pepper and sandalwood.
 True myrrh and frankincense from Yemen reached
the Mediterranean by 300 BC, by way of Persian
traders.
 Demand increased for roses, sweet flag, orris root,
narcissus, saffron, mastic, oak moss, cinnamon,
cardamom, pepper, nutmeg, ginger, costus,
spikenard, aloewood, grasses and gum resins.
 The shaping of history – Rome
By the 1st century AD, Rome was using about 2,800 tons of
imported frankincense and 550 tons of myrrh per year.
Nero, Roman emperor in 54 AD, spent the equivalent of
$100,000 to scent just one party he was giving. No “Orgy”
was complete without perfume.
 The Modern Toga Party
Former Tyco CEO Dennis Kozlowski

Today’s Nero
 The shaping of history – Biblical Times
Fragrance occurs, at least symbolically,
throughout the New Testament. The
frankincense and myrrh brought to the Christ
child were more valuable than the gift of gold
(if indeed it was gold; some speculate that the
three wise men may have been carrying gold-
colored, fragrant ambergris).
"Then took Mary a pound of ointment of

spikenard, very costly, and anointed the feet of
Jesus, and wiped his feet with her hair: and the
house was filled with the odour of the
ointment."
John 12:3
 The shaping of history – 1ST Century AD
Mary Prophetissa (Prophetissima) aka Maria the Jewess
The tribokos
Invented the double boiler, also known as a Bain Marie, or

Mary's Bath… as well as the first true still which she called
the tribokos. It consisted of copper tubing, ceramic pottery,
and metal. When heated, vapors from plant material and
water would condense on the inside of the still, then trickle
down and collect in a bottle.
 The shaping of history – 1ST Century AD
Mary Prophetissa (Prophetissima) aka Maria the Jewess
Her design and many later modifications were used to

distill essential oils, but also proved useful for alcoholic
beverages.
And with the still dawned the new Age of Alchemy
 The shaping of history – 10 -11th Century AD
Ibn Sina (Avicenna) – a famous Arab physician and
alchemist that wrote over 400 books on medicine,
philosophy, geology, mathematics, astronomy, and logic, is
credited with significantly improving the art of distillation by
adding a water cooled jacket around the cooling coil.
 The shaping of history – 10-14th Century AD
The Arabs used their new technique to distill ethyl
alcohol (ethanol) from fermented sugar, providing a new
solvent for the extraction of plant oils in place of the fatty
oils that had been used for millennia.
Knowledge of distillation gradually spread around

Europe through trading and crusading until essential oils
had become a specialty of mediaeval pharmacies.
Essential oils were so-named because they were

thought to represent the very essence of odor, flavor &
life. Their extraction was researched by alchemists in
their search for the philosophers' stone that would turn
common metals into gold.
 The shaping of history – Marco Polo
1271 - Marco Polo, at the age of seventeen years,

embarked from Venice with his father and uncle on a trip
that would last 24 years – and bring knowledge of the
Orient and trade routes.
Marco Polo lived for 16 years in China where he was
employed for several years by Kublai Khan. He left
China in 1292, returning to Venice (1295), and fought
against the Genoese, but was captured.
In prison he wrote of his adventures in 'Travels of
Marco Polo' - a book which instantly fired the
imagination of all Medieval Europe – and spurred a
competition among nations that would last 500 years.
 The shaping of history – Marco Polo
 The shaping of history – Influence of Spice Trade
In the 13th and 14th centuries, Italy monopolized

the European Spice & Perfume material trade that
had begun during the Crusades.
One purpose of Marco Polo's journey to China

was to bypass Moslem middlemen and their 300
percent markup in price by convincing the Orient to
trade directly with Venice.
 The shaping of history – The Age of Exploration
 1492 - Columbus discovered the Americas while

looking for the spice islands of the Orient.
Although, at the time, this failure was a great
disappointment – there were many treasures that
resulted. Vast quantities of gold, silver as well as
new culinary items such as chocolate (cocoa).
New fragrant treasures such as Vanilla, balsam of

Peru and Tolu, juniper, American cedar and
sassafras soon became available to Europeans.
 The shaping of history – Influence of Spice Trade
1497 - Vasco da Gama departs Lisbon Portugal to
discover the sea passage to the distant spice Indies.
1498 - Vasco da Gama arrives in India by rounding Africa
via the Cape of Good Hope and Portugal becomes the
ruler of the Indian ocean for nearly 150 years.
 The shaping of history – The Age of Colonization
 1602 - Dutch East India Company granted a

monopoly on the trade in the East Indies.
 Purpose - trading spices like nutmeg, cloves,
cinnamon and pepper, tea, silk and porcelain
And – to prevent other European nations from
entering the East Indies for trade.
 Dec. 31, 1600 - Queen Elizabeth I grants a Royal
Charter to the East India Company, but the Dutch
massacre of the English at Amboyna in 1623
reduced them initially to picking up scraps of trade,
either by piracy or dealing with intermediaries.
 The shaping of history – The Age of Colonization
 By the mid 1600’s – the Dutch had driven the
British and Portuguese from Indonesia, Malaya,
and Ceylon (Sri Lanka), and controlled the fabulous
trade of the Spice Islands.
 1621 - the Dutch started a West India Company,
which established the American province of New
Netherland in 1624, and reputedly purchased what
is now New York from the Native Americans for the
equivalent of $24.
 1664 - the English capture New Netherland
 1673 - New York was recaptured by a Dutch fleet
 1674 – The English negotiate peace and trade a
small island off Indonesia (Rhun) for New York.
 The shaping of history – Spice Wars
New York traded for Rhun – the best Nutmeg island
Quite A Trade
 The New Perfumers
 Perfumed leather gloves became popular in France

and in 1656, the guild of glove and perfume-makers was
established in Grasse. The use of perfume in France
grew steadily. The court of Louis XV was even named
“the perfumed court”.
In 1732, when the Italian Giovanni Maria Farina took

over his uncle's business in Cologne, he produced aqua
admirabilis, a lively blend of neroli, bergamot, lavender
and rosemary in rectified grape spirit. This was splashed
on the skin, and also used for treating sore gums and
indigestion. French soldiers later stationed there dubbed
it “eau de Cologne”.
 The shaping of history – France & Perfume
16th & 17th centuries - Southern France (Grasse)
becomes a center of expertise for the growing, extraction
and distillation of essential oils.
France becomes the the Perfume center of the world.
Large scale cultivation & processing of valuable plants for
oils such as rose soon was centered there. And raw
materials from around the world were imported for
processing. Extraction & distillation techniques were
refined.
 The shaping of history – France & Perfume
 Grasse France – The Center of Perfumery
Perfume Factory - Grasse
Lavender field near Grasse

 The Perfumers – Enfleurage process
Flowers such as Jasmine are laid out on trays of fat that
absorb the fragrance. The fat is later extracted with
alcohol,and then concentrated into an absolute.
Jasmine flowers laid out on the fat
Preparing the frame with fat

Grasse - Chiris factory - early 20th century
 The Production of Rose Oil
 The Production of Rose Oil
 The new partner – The Organic Chemist
Mid-1800’s - From Germany came a new breed of

Chemist that would revolutionize industry and bring an end
to “Alchemy”. This type chemist used the scientific method
to unravel chemical structures and create materials from
coal, petroleum and other materials.
1855 – First synthesis of cinnamaldehyde

1868 – Commercial production of coumarin – the first
synthetic fragrance chemical
1874 – Chemical structure of vanillin determined.
1876 – Synthetic vanillin production starts.
1850 to 1900 – Significant advances in elucidating
major chemicals in Essential oils.
Nobel Prize in Chemistry 1910 – Otto Wallach
Helps elucidate many of the C10H16 group terpene
structures present in essential oils utilizing common
reagents such as hydrogen chloride and hydrogen
bromide. In 1909 he published the results of his extensive
studies in the book Terpene und Campher, a volume of
600 pages dedicated to his pupils.
CH3 CH3
CH3 CH2
H3C H3C
alpha-Pinene beta-Pinene
CH3
H3C
CH2
CH3
H3C CH3
O
Camphor Camphene
The new partner – The Organic Chemist
Nobel Prize in Chemistry 1939 - Leopold Ruzicka
In the perfumery and sesquiterpene domain - the total
syntheses of nerolidol and farnesol.
From Jasmine - established the structure of jasmone.
Elucidated the structures of the naturally occurring
musk perfumes, civetone and muscone thus replacing
scents prized since antiquity – but only available from
endangered species.
O
O CH3
Civetone Musk Deer Muscone

Civet Cat
Viverra civetta Moschus moschiferus L.
Nobel Prize in Chemistry 2001 - Ryoji Noyori
For chirally catalyzed hydrogenation reactions.
In perfumery and flavors - the chiral (asymmetric)
synthesis of Menthol & many other fragrance & flavor
compounds.
In the chiral synthesis of pharmaceutical & photochromic
materials.
CH3 CH3
OH HO
H3C CH3 H3C CH3

1950’s – Bain & Webb – Turpentine into Fragrance & Flavor
O
H3C
CH3 H3C OH CH3
CH2 H3C O
H3C
CH2
CH2
OH
beta-Pinene
H3C CH3 H3C CH3

H3C CH3
CH2 Linalool Menthol
Linalyl Acetate
CH2 CH3 CH3 CH3
H3C CH3
Myrcene OH OH O
H3C CH3 H3C CH3 H3C CH3
Geraniol Citronellol Citronellal

 Gas Chromatography – Mass Spectrometry
GC-MS analysis Detective work
Distillation & extraction Volatiles from a living flower

GC-MS Analysis of a Meat Flavor

Abundance
Peak Identified as Furfuryl Mercaptan SH

1.6e+07 Powerful Coffee Aroma O
1.4e+07
Peaks are 2-Methyl-2,3-dihydrofuran-3-thiol isomers
1.2e+07 Powerful meat-like aroma
SH SH
1e+07
8000000
CH3 CH3
O O
6000000
4000000
2000000
0
12.00 14.00 16.00 18.00 20.00 22.00 24.00 26.00 28.00 30.00 32.00 34.00 36.00
Time-->
Volatile Chemicals Identified in
Foodstuffs
8000
7000
6000
Thousands
5000
4000
3000
2000
1000
0
1963
1969
1974
1979
1984
1989
1994
1999
 Rose oil – What’s Important
Concentration
CH3 Odor Unit =
Odor Threshold
Rel. %
OH
Threshold in Odor Units of odor
Component % of Oil ppb x 10-3 units
H3C CH3 (-)-Citronellol 38 40 9500 4.3
CH3 C14 - C16 Paraffins 16 - - -
Geraniol 14 75 1860 0.8
Nerol 7 300 233 0.1
Phenethyl alcohol 2.8 750 37 0.016
O Eugenol methyl ether 2.4 820 29 0.013
Eugenol 1.2 30 400 0.18
H3C CH3 Farnesol 1.2 20 600 0.27
O Linalool 1.4 6 2300 1
H3C CH3 (-)-Rose oxide 0.46 0.5 9200 4.1
(-)-Carvone 0.41 50 82 0.036
CH3
Rose furan 0.16 200 8 0.003
beta-Damascenone 0.14 0.009 156000 70
CH3
beta-Ionone 0.03 0.007 42860 19.2
H3C CH3 O
CH3
CH3
 Perfumery - The Image of an Artist
Parfume de Campange by Guy Begin

 The Perfumer – An artist with a different palette
 Marketing- The Image
The Allure of Perfume is popularized by marketing
France - late 19th century Spain - 1903 France - circa 1935

Marketing- The Image
The Allure of Perfume is popularized by marketing
Zica-Alexa - Year 2000

OLFACTION & GUSTATION
Multidisciplinary Fields
•Fragrances
Perfume
Soap/ Detergent /Air Fresheners / Aromatherapy
•Flavors – Food Science

Food Products
Beverages
Chewing Gum/ Mouthwash/ Pharmaceuticals
Tobacco
OLFACTION & GUSTATION
Multidisciplinary Fields
•Chemistry/ Biology/ Physiology/ Psychology

- Organic Chemistry – Synthetic, Molecular structure,
Biochemistry, Molecular Biology, Genomics,
Anatomy, Neuroscience, Bioinformatics
- Analytical Chemistry – GC-MS analysis, Quality
Assurance
- Physical Chemistry – Emulsions, Light scattering, etc.
- Psychological aspects of perception – other influences
•Computer Science – for all of the above +

TASTE = GUSTATION
Taste (Gustation) - sensitivity to substances in solution

Taste Buds in epithelium of tongue, soft palate, pharynx, larynx
and epiglottis.
2000-5000 taste buds in humans, but large variation.
TASTE = GUSTATION
Until the mid 1990’s only 4 taste sensations

were recognized:
• Sweet – e.g. Sucrose, Aspartame
• Sour – e.g. Citric acid, Phosphoric acid (H+ ions)
• Bitter – e.g. Quinine
• Salty – Sodium Chloride
A 5th taste sensation called “Umani” is now
recognized. Most common example is MSG
(Monosodium glutamate) which enhances meat
flavor.
SMELL = OLFACTION
Smell (Olfaction) - sensitivity to substances in gaseous

phase - a distant sense
How We Smell -
Olfactory Region (Regio olfactoria)
Odorants are volatile chemicals carried by inhaled air to the Regio

olfactoria (olfactory epithelium) located in the roof of the two nasal cavities
of the human nose, just below and between the eyes.
The olfactory region of each of the two nasal passages in humans is a small
area of about 2.5 square centimeters containing in total approximately 50
million primary sensory receptor cells.
 New Technology – How We Smell
Olfactory Nerve Olfactory Bulb

Mitral Cell
Olfactory Tract
Glomerulli
Olfactory Nerve Filaments
Cribiform (bone)
Axons
Olfactory Receptor Neurons Olfactory

Epithelium
Cilia in Mucosa Mucosa
Air and
Odorant Molecules
The olfactory region consists of cilia projecting down out of the olfactory
epithelium. The olfactory cilia are the sites where molecular reception with the
odorant occurs and sensory transduction (i.e., transmission) starts.
 New Technology – Understanding Scent
Elucidation of Olfactory G-Protein Receptor

Structures - a result of Genome Research
Different Views of G-Protein Receptor Structures
900+ Human Olfactory Receptor Genes Identified – D. Lancet

~600 Pseudogenes + ~300 Intact Genes
 New Technology – Understanding Scent
Putative Binding cavity in Human OR1.04.06

derived using CastP
Computer Modeling of New Odorants
Olfactophoric Model of Sandalwood Odorants

Javanol (Yellow) vs. beta-Santalol (Blue)
 New Technology – Digital Scent
Hardware and software platforms for incorporating scent into all forms of
media...
Peripheral devices that recreate thousands of scents on demand.
Authoring tools for the creation of "scent scores" for movies, music, and
interactive games.
Software that plays scented media, such as videos, music and DVD's.
Systems for transmitting scent with music and movies over the Internet.
And…for the Perfumer & Flavorist – A new tool for composing creations.
Flavor Research
The Proof is in the Pudding
Chef’s and flavor application specialists

determine use levels and food applications.
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See discussions, stats, and author profiles for this publication at: https://www.researchgate.

The Art & Science of Fragrance & Flavor Creation

Conference Paper · December 2003

Fusarium Mycotoxins View project

Agarwood View project

The user has requested enhancement of the downloaded file.

Society of Flavor Chemist’s

Middle East & Asia-Pacific

12.8% - Givaudan (CH)

7.6% - Quest Int'l (NL)

Sensient - 2.8% (US)

 Prehistory - Culinary & Fragrant Oils

 Circa 7000 BC – Fragrant plants and spices

 3000 BC – Indus Valley (Pakistan) - terra-cotta

 3000 BC – Egyptians– when learning to write and

Perfume Vessel Symbolizing Unification - Reign of

Greek Perfume Urns

 Socrates’ classmate, Theophrastus, sent plant

 Theophrastus' treatise “On Odors” covered all the

 As trade routes expanded, Africa, South Arabia and

Former Tyco CEO Dennis Kozlowski

"Then took Mary a pound of ointment of

Invented the double boiler, also known as a Bain Marie, or

Her design and many later modifications were used to

Knowledge of distillation gradually spread around

Essential oils were so-named because they were

1271 - Marco Polo, at the age of seventeen years,

In the 13th and 14th centuries, Italy monopolized

One purpose of Marco Polo's journey to China

 1492 - Columbus discovered the Americas while

New fragrant treasures such as Vanilla, balsam of

 1602 - Dutch East India Company granted a

 Perfumed leather gloves became popular in France

In 1732, when the Italian Giovanni Maria Farina took

Perfume Factory - Grasse

Lavender field near Grasse

Jasmine flowers laid out on the fat

Preparing the frame with fat

Mid-1800’s - From Germany came a new breed of

1855 – First synthesis of cinnamaldehyde

Civetone Musk Deer Muscone

H3C CH3 H3C CH3

H3C CH3 H3C CH3

CH2 CH3 CH3 CH3

H3C CH3 H3C CH3 H3C CH3

Geraniol Citronellol Citronellal

GC-MS analysis Detective work

Distillation & extraction Volatiles from a living flower

GC-MS Analysis of a Meat Flavor

Peak Identified as Furfuryl Mercaptan SH

Parfume de Campange by Guy Begin

France - late 19th century Spain - 1903 France - circa 1935

Zica-Alexa - Year 2000

OLFACTION & GUSTATION

•Flavors – Food Science

•Chemistry/ Biology/ Physiology/ Psychology

•Computer Science – for all of the above +

Taste (Gustation) - sensitivity to substances in solution

Until the mid 1990’s only 4 taste sensations

Smell (Olfaction) - sensitivity to substances in gaseous

Olfactory Region (Regio olfactoria)

Odorants are volatile chemicals carried by inhaled air to the Regio

Olfactory Nerve Olfactory Bulb