Aroma compound

From Wikipedia, the free encyclopedia

An aroma compound, also known as 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, perfumes, fragrance oils, and essential oils. For
example, many form biochemically during 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 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 warning.

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 References
7 See also

Aroma compounds classified by structure

Esters

Compound name

Fragrance

Geranyl acetate

Fruity, Rose

Methyl formate

Ethereal

Methyl acetate

Sweet, nail polish

Solvent

Natural occurrence
Rose,
Floral

Methyl propionate
Sweet, fruity, rum-like
Methyl propanoate
Methyl butyrate
Methyl butanoate

Fruity, Apple
Pineapple

Pineapple

Ethyl acetate

Sweet, solvent

Wine

Ethyl butyrate
Ethyl butanoate

Fruity, Orange
Pineapple

Isoamyl acetate

Fruity, Banana
Pear

Pentyl butyrate
Pentyl butanoate

Fruity, Pear
Apricot

Pentyl pentanoate

Fruity, Apple

Octyl acetate

Fruity, Orange

Benzyl acetate

Fruity, Strawberry

Methyl anthranilate

Fruity, Grape

Linear terpenes

Banana plant

Strawberries

Chemical structure

Compound name

Fragrance

Natural occurrence

Myrcene

Woody, complex

Verbena, Bay leaf

Geraniol

Rose, flowery

Geranium, Lemon

Nerol

Sweet rose, flowery

Neroli, Lemongrass

Citral, lemonal
Geranial, neral

Lemon

Lemon myrtle, Lemongrass

Citronellal

Lemon

Lemongrass

Citronellol

Lemon

Lemongrass, rose
Pelargonium

Linalool

Floral, sweet
Woody, Lavender

Coriander, Sweet basil

Lavender

Nerolidol

Woody, fresh bark

Neroli, ginger
Jasmine

Cyclic terpenes

Chemical structure

Compound name

Fragrance

Natural occurrence Chemical structure

Limonene

Orange

Orange, lemon

Camphor

Camphor

Camphor laurel

Menthol

Menthol

Mentha

Carvone1

Caraway or Spearmint

Caraway, dill,
spearmint

Terpineol

Lilac

Lilac, cajuput

alpha-Ionone

Violet, woody

Violet

Thujone

Minty

Wormwood, lilac,
juniper

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

Aromatic

Compound name

Fragrance

Benzaldehyde

Almond

Bitter almond

Eugenol

Clove

Clove

Cinnamaldehyde

Cinnamon

Cassia
Cinnamon

Ethyl maltol

Cooked fruit
Caramelized sugar

Vanillin

Vanilla

Vanilla

Anisole

Anise

Anise

Anethole

Anise

Anise
Sweet basil

Estragole

Tarragon

Tarragon

Thymol

Thyme

Thyme

Amines

Natural occurrence Chemical structure

Compound name Fragrance

Natural occurrence

Trimethylamine

Fishy
Ammonia

Putrescine
Diaminobutane

Rotting flesh

Rotting flesh

Cadaverine

Rotting flesh

Rotting flesh

Pyridine

Fishy

Belladonna

Indole

Fecal
Flowery

Feces
Jasmine

Skatole

Fecal

Feces
(diluted) Orange Blossoms

Chemical structure

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)

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
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 normal 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 (Green Apple, 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 olfactory receptors. Olfactory receptors are
cell membrane receptors on the surface of sensory neurons in the olfactory system that detect air-borne
aroma compounds.

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 further review or testing and put the burden of
proof that a new substance is not safe on the EPA. The EPA,

Patch test

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% world's production volume of
fragrances.[9]

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". PLoS ONE 8: e55780. doi:10.1371/journal.pone.0055780
(https://dx.doi.org/10.1371%2Fjournal.pone.0055780).
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): 7006
7009. doi:10.1002/anie.200602100 (https://dx.doi.org/10.1002%2Fanie.200602100). PMID 17009284
(https://www.ncbi.nlm.nih.gov/pubmed/17009284).
4. Block, E. (2010). Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry. ISBN 0-85404190-7.
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. doi:10.1038/nature03414 (https://dx.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 2005
2006. Dermatitis. 2009 MayJun;20(3):149-60.
7. Toxic chemicals linked to birth defects are being found at alarming levels in women of childbearing age
(http://www.ewg.org/reports/nottoopretty/)
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.

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

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Categories: Organic chemistry Olfaction Flavors Perfume ingredients
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