7/5/2017 Aroma compound - Wikipedia

Aroma compound
From Wikipedia, the free encyclopedia

An aroma compound, also known as an odorant, aroma, fragrance, or

flavor, is a chemical compound that has a smell or odor. A chemical
compound has a smell or odor when it is sufficiently volatile to be
transported to the olfactory system in the upper part of the nose.

Generally molecules meeting this specification have molecular weights of

<300. Flavors affect both the sense of taste and smell, whereas fragrances
affect only smell. Flavors tend to be naturally occurring, and fragrances
tend to be synthetic.[1]

Aroma compounds can be found in food, wine, spices, floral scent,

perfumes, fragrance oils, and essential oils. For example, many form
biochemically during the ripening of fruits and other crops. In wines, most
form as byproducts of fermentation. Also, many of the aroma compounds
play a significant role in the production of flavorants, which are used in the Fragrance bottles.
food service industry to flavor, improve, and generally increase the appeal
of their products.

An odorizer may add an odorant to a dangerous odorless substance, like propane, natural gas, or hydrogen, as a
safety measure.

Contents
1 Aroma compounds classified by structure
1.1 Esters
1.2 Linear terpenes
1.3 Cyclic terpenes
1.4 Aromatic
1.5 Amines
2 Other aroma compounds
2.1 Alcohols
2.2 Aldehydes
2.3 Esters
2.4 Ketones
2.5 Lactones
2.6 Thiols
2.7 Miscellaneous compounds
3 Aroma-compound receptors
4 Safety
5 List of chemicals used as fragrances
6 See also
7 References

Aroma compounds classified by structure

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Esters

Compound name Fragrance Natural occurrence Chemical structure

Rose,
Geranyl acetate Fruity, Rose
Floral

Methyl formate Ethereal

Sweet, nail polish

Methyl acetate
Solvent
Methyl propionate
Sweet, fruity, rum-like
Methyl propanoate
Methyl butyrate Fruity, Apple
Pineapple
Methyl butanoate Pineapple

Ethyl acetate Sweet, solvent Wine

Ethyl butyrate Fruity, Orange

Ethyl butanoate Pineapple
Fruity, Banana
Isoamyl acetate Banana plant
Pear
Pentyl butyrate Fruity, Pear
Pentyl butanoate Apricot

Pentyl pentanoate Fruity, Apple

Octyl acetate Fruity, Orange

Benzyl acetate Fruity, Strawberry Strawberries

Methyl anthranilate Fruity, Grape

Linear terpenes

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Compound name Fragrance Natural occurrence Chemical structure

Myrcene Woody, complex Verbena, Bay leaf

Geraniol Rose, flowery Geranium, Lemon

Nerol Sweet rose, flowery Neroli, Lemongrass

Citral, lemonal
Lemon Lemon myrtle, Lemongrass
Geranial, neral

Citronellal Lemon Lemongrass

Lemongrass, rose
Citronellol Lemon
Pelargonium
Floral, sweet Coriander, Sweet basil
Linalool
Woody, Lavender Lavender
Neroli, ginger
Nerolidol Woody, fresh bark
Jasmine

Cyclic terpenes

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Compound name Fragrance Natural occurrence Chemical structure

Limonene Orange Orange, lemon

Camphor Camphor Camphor laurel

Menthol Menthol Mentha

Caraway, dill,
Carvone1 Caraway or Spearmint
spearmint

Terpineol Lilac Lilac, cajuput

alpha-Ionone Violet, woody Violet

Wormwood, lilac,
Thujone Minty
juniper

Eucalyptol Eucalyptus Eucalyptus globulus

Note: Carvone, depending on its chirality, offers two different smells.

Aromatic

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Compound name Fragrance Natural occurrence Chemical structure

Benzaldehyde Almond Bitter almond

Eugenol Clove Clove

Cassia
Cinnamaldehyde Cinnamon
Cinnamon

Cooked fruit
Ethyl maltol
Caramelized sugar

Vanillin Vanilla Vanilla

Anisole Anise Anise

Anise
Anethole Anise
Sweet basil

Estragole Tarragon Tarragon

Thymol Thyme Thyme

Amines

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Compound name Fragrance Natural occurrence Chemical structure

Fishy
Trimethylamine
Ammonia
Putrescine
Rotting flesh Rotting flesh
Diaminobutane

Cadaverine Rotting flesh Rotting flesh

Pyridine Fishy Belladonna

Fecal Feces
Indole
Flowery Jasmine

Feces
Skatole Fecal
(diluted) Orange Blossoms

Other aroma compounds

Alcohols

Furaneol (strawberry)
1-Hexanol (herbaceous, woody)
cis-3-Hexen-1-ol (fresh cut grass)
Menthol (peppermint)

Aldehydes

High concentrations of aldehydes tend to be very pungent and overwhelming, but low concentrations can evoke a
wide range of aromas.

Acetaldehyde (ethereal)
Hexanal (green, grassy)
cis-3-Hexenal (green tomatoes)
Furfural (burnt oats)
Hexyl cinnamaldehyde
Isovaleraldehyde nutty, fruity, cocoa-like
Anisic aldehyde floral, sweet, hawthorn. It is a crucial component of chocolate, vanilla, strawberry,
raspberry, apricot, and others.
Cuminaldehyde (4-propan-2-ylbenzaldehyde) Spicy, cumin-like, green

Esters
Fructone (fruity, apple-like)
Hexyl acetate (apple, floral, fruity)
Ethyl methylphenylglycidate (strawberry)

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Ketones

Cyclopentadecanone (musk-ketone)[2]
Dihydrojasmone (fruity woody floral)
Oct-1-en-3-one (blood, metallic, mushroom-like)[3]
2-Acetyl-1-pyrroline (fresh bread, jasmine rice)
6-Acetyl-2,3,4,5-tetrahydropyridine (fresh bread, tortillas, popcorn)

Lactones

gamma-Decalactone intense peach flavor

gamma-Nonalactone coconut odor, popular in suntan lotions
delta-Octalactone creamy note
Jasmine lactone powerful fatty-fruity peach and apricot
Massoia lactone powerful creamy coconut
Wine lactone sweet coconut odor
Sotolon (maple syrup, curry, fenugreek)

Thiols

Thioacetone (2-propanethione) A lightly studied organosulfur. Its smell is so potent it can be detected
several hundred meters downwind mere seconds after a container is opened.
Allyl thiol (2-propenethiol; allyl mercaptan; CH2=CHCH2SH) (garlic volatiles and garlic breath)[4]
(Methylthio)methanethiol (CH3SCH2SH), the "mouse thiol", found in mouse urine and functions as a
semiochemical for female mice[5]
Ethanethiol, commonly called ethyl mercaptan (added to propane or other liquefied-petroleum gases used as
fuel gases)
2-Methyl-2-propanethiol, commonly called tert-butyl mercaptan, is added as a blend of other components to
natural gas used as fuel gas.
Butane-1-thiol, commonly called butyl mercaptan, is a chemical intermediate.
Grapefruit mercaptan (grapefruit)
Methanethiol, commonly called methyl mercaptan (after eating Asparagus)
Furan-2-ylmethanethiol, also called furfuryl mercaptan (roasted coffee)
Benzyl mercaptan (leek or garlic-like)

Miscellaneous compounds

Methylphosphine and dimethylphosphine (garlic-metallic, two of the most potent odorants known)[3]
Phosphine (Zinc Phosphide poisoned bait)
Diacetyl (Butter flavor)
Acetoin (Butter flavor)
Nerolin (orange flowers)
Tetrahydrothiophene (added to natural gas)
2,4,6-Trichloroanisole (cork taint)
Substituted pyrazines

Aroma-compound receptors
Animals that are capable of smell detect aroma compounds with their olfactory receptors. Olfactory receptors are
cell-membrane receptors on the surface of sensory neurons in the olfactory system that detect airborne aroma
compounds.
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In mammals, olfactory receptors are expressed on the surface of the olfactory epithelium in the nasal cavity.

Safety
In 200506, fragrance mix was the third-most-prevalent allergen in patch
tests (11.5%).[6]

'Fragrance' was voted Allergen of the Year in 2007 by the American

Contact Dermatitis Society. The composition of fragrances is usually not
disclosed in the label of products, hiding the actual chemicals of the
formula, which raises concerns among some consumers.[7]

Fragrances are regulated in the United States by the Toxic Substances

Control Act of 1976 that "grandfathered" existing chemicals without
Patch test
further review or testing and put the burden of proof that a new substance is
not safe on the EPA. The EPA, however, does not conduct independent
safety testing but relies on data provided by the manufacturer.[8]

List of chemicals used as fragrances

In 2010 the International Fragrance Association published a list of 3,059 chemicals used in 2011 based on a
voluntary survey of its members. It was estimated to represent about 90% of the world's production volume of
fragrances.[9]

See also
Flavour and Fragrance Journal
Fragrances of the World
Foodpairing
Odor
Odor detection threshold
Olfaction
Olfactory system
Olfactory receptor
Odorizer, a device for adding an odorant to gas flowing through a pipe
Pheromone
Aroma of wine
Eau de toilette

References
1. Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, ,
Kurt Bauer, Dorothea Garbe and Horst Surburg "Flavors and Fragrances" Ullmann's Encyclopedia of Industrial
Chemistry, 2003, Wiley-VCH. doi:10.1002/14356007.a11_141 (https://dx.doi.org/10.1002%2F14356007.a11_141)
2. Gane, S; Georganakis, D; Maniati, K; Vamvakias, M; Ragoussis, N; Skoulakis, EMC; Turin, L (2013). "Molecular-
vibration-sensing component in human olfaction" (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3555824). PLoS
ONE. 8: e55780. PMC 3555824 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3555824) . PMID 23372854 (https://
www.ncbi.nlm.nih.gov/pubmed/23372854). doi:10.1371/journal.pone.0055780 (https://doi.org/10.1371%2Fjournal.pone.
0055780).

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3. Glindemann, D.; Dietrich, A.; Staerk, H.; Kuschk, P. (2005). "The Two Odors of Iron when Touched or Pickled: (Skin)
Carbonyl Compounds and Organophosphines". Angewandte Chemie International Edition. 45 (42): 70067009.
PMID 17009284 (https://www.ncbi.nlm.nih.gov/pubmed/17009284). doi:10.1002/anie.200602100 (https://doi.org/10.10
02%2Fanie.200602100).
4. Block, E. (2010). Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry. ISBN 0-85404-190-
7.
5. Lin, D.Y.; Zhang, S.Z.; Block, E.; Katz, L.C. (2005). "Encoding social signals in the mouse main olfactory bulb".
Nature. 434: 470477. PMID 15724148 (https://www.ncbi.nlm.nih.gov/pubmed/15724148). doi:10.1038/nature03414 (h
ttps://doi.org/10.1038%2Fnature03414).
6. Zug KA, Warshaw EM, Fowler JF Jr, Maibach HI, Belsito DL, Pratt MD, Sasseville D, Storrs FJ, Taylor JS, Mathias
CG, Deleo VA, Rietschel RL, Marks J. Patch-test results of the North American Contact Dermatitis Group 20052006.
Dermatitis. 2009 MayJun;20(3):149-60.
7. Toxic chemicals linked to birth defects are being found at alarming levels in (http://www.ewg.org/reports/nottoopretty/)
women (http://el-mejor.com/perfumes/de-mujer/) of childbearing age
8. Randall Fitzgerald. The Hundred Year Lie. Dutton, 2006. p. 23. ISBN 0-525-94951-8.
9. "IFRA Survey:Transparency List" (http://www.ifraorg.org/en-us/ingredients#.VH-EkXsdXYg). IFRA. Retrieved
December 3, 2014.

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