Art & Science of Flavor & Fragrance Creation
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Transcript of Art & Science of Flavor & Fragrance Creation
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The Art & Science of Fragrance & Flavor Creation
Society of Flavor Chemist’s
December 4, 2003
John C. Leffingwell
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Fragrance & Flavor – Art & Science
Conventional Market View – U.S. $15 Billion
Worldwide MarketFlavors vs. Fragrances
Flavors49%
Fragrances51%
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Fragrance & Flavor – Art & Science
Conventional Market View – U.S. $15 Billion
Eastern Europe
5%
Middle East & Africa
6%
25% 32%
26%South America
6%
NorthAmerica
Asia-Pacific
WesternEurope
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Fragrance & Flavor – Art & Science
Conventional Market View – U.S. $15 Billion
Flavor & Fragance Market excludingBranded Soft Drink Concentrates
Others - 35.4%
Sensient - 2.8% (US)
T. Hasegaawa - 2.5 % (JP)
Mane - 1.8% (FR)
Takasago - 5.6% (JP)
8.6% - Symrise (DE)
9.1% - Firmenich (CH)
7.6% - Quest Int'l (NL)
12.8% - Givaudan (CH)
12% - International Flavors & Fragrances
(US)
Danisco - 1.7% (DK)
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Fragrance & Flavor – Art & Science
The Real Market – U.S. $30 BillionFlavor & Fragrance Market
Including Branded Soft Drink Concentrates
3% 3%
16%
39%
39%
Coca-Cola
Pepsico
Flavor &Fragrance
Cadbury Schweppes
Other Branded Soft Drinks
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Fragrance & Flavor – Art & Science
Fragrance & Flavor - The shaping of history
Prehistory - Culinary & Fragrant Oils
Circa 7000 BC – Fragrant plants and spices infused in the fatty oils of Olive & Sesame for use as ointments
Earliest items of commerce were most likely spices, gums and other fragrant plants.
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Fragrance & Flavor – Art & Science
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.
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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
Fragrance & Flavor – Art & Science The shaping of history - Egypt
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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.
Fragrance & Flavor – Art & Science The shaping of history – Greece
Greek Perfume Urns
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Leucippus and Democritus – Fathers of the Atomic Theory
Fragrance & Flavor – Art & Science The shaping of history – Greece circa 400 BC
Still of Democritus
The first firm documentary evidence of the distillation of essential oils is Herodotus' record of the method of distilling turpentine from 425 B.C.
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Fragrance & Flavor – Art & Science 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.
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Fragrance & Flavor – Art & Science 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.
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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.
Fragrance & Flavor – Art & Science The shaping of history – Rome
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Former Tyco CEO Dennis KozlowskiToday’s Nero
Fragrance & Flavor – Art & Science
The Modern Toga Party
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"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
Fragrance & Flavor – Art & Science 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).
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Mary Prophetissa (Prophetissima) aka Maria the Jewess
Fragrance & Flavor – Art & Science The shaping of history – 1ST Century AD
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 tribokos
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Mary Prophetissa (Prophetissima) aka Maria the Jewess
Fragrance & Flavor – Art & Science The shaping of history – 1ST Century AD
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
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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.
Fragrance & Flavor – Art & Science The shaping of history – 10 -11th Century AD
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Fragrance & Flavor – Art & Science 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.
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Fragrance & Flavor – Art & Science 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.
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Fragrance & Flavor – Art & Science The shaping of history – Marco Polo
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Fragrance & Flavor – Art & Science 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.
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Fragrance & Flavor – Art & Science 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.
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Fragrance & Flavor – Art & Science 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.
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Fragrance & Flavor – Art & Science 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 porcelainAnd – 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.
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Fragrance & Flavor – Art & Science 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.
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Fragrance & Flavor – Art & Science The shaping of history – Spice Wars
New York traded for Rhun – the best Nutmeg island
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Quite A Trade
Fragrance & Flavor – Art & Science
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Fragrance & Flavor – Art & Science 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”.
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Fragrance & Flavor – Art & Science 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.
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Fragrance & Flavor – Art & Science The shaping of history – France & Perfume
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Fragrance & Flavor – Art & Science Grasse France – The Center of Perfumery
Perfume Factory - Grasse
Lavender field near Grasse
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Fragrance & Flavor – Art & Science 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
Grasse - Chiris factory - early 20th century
Preparing the frame with fat
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Fragrance & Flavor – Art & Science The Production of Rose Oil
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Fragrance & Flavor – Art & Science The Production of Rose Oil
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Fragrance & Flavor – Art & Science 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 cinnamaldehyde1868 – 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.
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Fragrance & Flavor – Art & Science The new partner – The Organic Chemist
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
CH3CH3
CH3
CH3CH2
CH2
CH3
CH3
CH3CH3
CH3O
beta-Pinenealpha-Pinene
CampheneCamphor
Nobel Prize in Chemistry 1910 – Otto Wallach
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Fragrance & Flavor – Art & Science The new partner – The Organic Chemist
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.
OO CH3
Civetone MusconeCivet CatViverra civetta
Musk DeerMoschus moschiferus L.
Nobel Prize in Chemistry 1939 - Leopold Ruzicka
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The new partner – The Organic Chemist
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.
Nobel Prize in Chemistry 2001 - Ryoji Noyori
Fragrance & Flavor – Art & Science
CH3
OH
CH3CH3
CH3
OH
CH3CH3
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Fragrance & Flavor – Art & Science The new partner – The Organic Chemist
CH3
CH3CH2
CH2
CH3 CH3
CH2
CH3
CH3 CH3
CH2
OH
CH3
CH3 CH3
OH
CH3
CH3 CH3
OH
CH3
CH3 CH3
O
CH3
CH3 CH3
OHbeta-Pinene
Myrcene
Linalool
Geraniol Citronellol Citronellal
Menthol
CH3
CH3 CH3
CH2
O
OCH3
Linalyl Acetate
1950’s – Bain & Webb – Turpentine into Fragrance & Flavor
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Fragrance & Flavor – Art & Science Gas Chromatography – Mass Spectrometry
GC-MS analysis Detective work
Distillation & extraction Volatiles from a living flower
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Fragrance & Flavor – Art & Science Gas Chromatography – Mass Spectrometry
12.00 14.00 16.00 18.00 20.00 22.00 24.00 26.00 28.00 30.00 32.00 34.00 36.000
2000000
4000000
6000000
8000000
1e+07
1.2e+07
1.4e+07
1.6e+07
Time-->
Abundance
GC-MS Analysis of a Meat Flavor
Peak Identified as Furfuryl MercaptanPowerful Coffee Aroma
Peaks are 2-Methyl-2,3-dihydrofuran-3-thiol isomersPowerful meat-like aroma
O
SH
CH3 O
SH
CH3
O
SH
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Fragrance & Flavor – Art & Science Gas Chromatography – Mass Spectrometry
Volatile Chemicals Identified in Foodstuffs
0
1000
2000
3000
4000
5000
6000
7000
8000
1963
1969
1974
1979
1984
1989
1994
1999
Th
ou
san
ds
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Fragrance & Flavor – Art & Science Rose oil – What’s Important
Component % of OilThreshold in
ppb
Odor Units
x 10-3
Rel. % of odor
units(-)-Citronellol 38 40 9500 4.3
C14 - C16 Paraffins 16 - - -
Geraniol 14 75 1860 0.8Nerol 7 300 233 0.1Phenethyl alcohol 2.8 750 37 0.016Eugenol methyl ether 2.4 820 29 0.013Eugenol 1.2 30 400 0.18Farnesol 1.2 20 600 0.27Linalool 1.4 6 2300 1(-)-Rose oxide 0.46 0.5 9200 4.1(-)-Carvone 0.41 50 82 0.036Rose furan 0.16 200 8 0.003beta-Damascenone 0.14 0.009 156000 70beta-Ionone 0.03 0.007 42860 19.2
Odor Unit =Concentration
Odor Threshold
O
CH3
CH3CH3
CH3CH3
CH3
CH3
O
CH3
CH3 CH3
OH
CH3 CH3
CH3
O
CH3
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Fragrance & Flavor – Art & Science Perfumery - The Image of an Artist
Parfume de Campange by Guy Begin
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Fragrance & Flavor – Art & Science The Perfumer – An artist with a different palette
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Fragrance & Flavor – Art & Science Marketing- The ImageThe Allure of Perfume is popularized by marketing
France - late 19th century France - circa 1935 Spain - 1903
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Fragrance & Flavor – Art & Science Marketing- The ImageThe Allure of Perfume is popularized by marketing
Zica-Alexa - Year 2000
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Fragrance & Flavor – Art & Science
Multidisciplinary Fields
•Flavors – Food Science Food Products Beverages Chewing Gum/ Mouthwash/ Pharmaceuticals Tobacco
•Fragrances Perfume Soap/ Detergent /Air Fresheners / Aromatherapy
OLFACTION & GUSTATION
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Fragrance & Flavor – Art & Science
•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
OLFACTION & GUSTATION
Multidisciplinary Fields
•Computer Science – for all of the above +
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Fragrance & Flavor – Art & Science
Taste Buds in epithelium of tongue, soft palate, pharynx, larynx and epiglottis. 2000-5000 taste buds in humans, but large variation.
Taste (Gustation) - sensitivity to substances in solution
TASTE = GUSTATION
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Fragrance & Flavor – Art & Science
TASTE = GUSTATION
Until the mid 1990’s only 4 taste sensationswere 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.
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Fragrance & Flavor – Art & Science
Smell (Olfaction) - sensitivity to substances in gaseous phase - a distant sense
SMELL = OLFACTION
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Fragrance & Flavor – Art & Science
How We Smell -
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.
Olfactory Region (Regio olfactoria)
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Fragrance & Flavor – Art & Science New Technology – How We Smell
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.
Olfactory TractMitral Cell
Olfactory Nerve Olfactory Bulb
OlfactoryEpithelium
Mucosa
Air and
Odorant Molecules
Cilia in Mucosa
Olfactory Receptor Neurons
Glomerulli
Olfactory Nerve Filaments
Cribiform (bone)
Axons
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Fragrance & Flavor – Art & Science 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
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Putative Binding cavity in Human OR1.04.06 derived using CastP
New Technology – Understanding Scent
Fragrance & Flavor – Art & Science
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Fragrance & Flavor – Art & Science
Computer Modeling of New Odorants
Olfactophoric Model of Sandalwood OdorantsJavanol (Yellow) vs. beta-Santalol (Blue)
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Fragrance & Flavor – Art & Science 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.
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Fragrance & Flavor – Art & Science
The Proof is in the Pudding
Chef’s and flavor application specialistsdetermine use levels and food applications.
Flavor Research