"Fragrance" redirects here. For other uses, see Fragrance (disambiguation).
"Fragrant" redirects here. For the community in the United States, see Fragrant, Kentucky.
"Odorants" redirects here. For the punk rock band, see The Odorants.
Not to be confused with Aromaticity.
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 |
Natural occurrence |
Chemical structure |
| Geranyl acetate |
Fruity, Rose |
Rose,
Floral |
|
| Methyl formate |
Ethereal |
|
|
| Methyl acetate |
Sweet, nail polish
Solvent |
|
|
Methyl propionate
Methyl propanoate |
Sweet, fruity, rum-like |
|
|
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 |
Banana plant |
|
Pentyl butyrate
Pentyl butanoate |
Fruity, Pear
Apricot |
|
|
| Pentyl pentanoate |
Fruity, Apple |
|
|
| Octyl acetate |
Fruity, Orange |
|
|
| Benzyl acetate |
Fruity, Strawberry |
Strawberries |
|
| Methyl anthranilate |
Fruity, Grape |
|
|
Linear terpenes
| 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
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
| 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 |
Natural occurrence |
Chemical structure |
| 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
| Compound name |
Fragrance |
Natural occurrence |
Chemical structure |
| 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 |
|
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
Main article: Thiol
- 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 2005–06, 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, 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
- ^ 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
- ^ 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.
- ^ a b 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. PMID 17009284.
- ^ Block, E. (2010). Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry. ISBN 0-85404-190-7.
- ^ Lin, D.Y.; Zhang, S.Z.; Block, E.; Katz, L.C. (2005). "Encoding social signals in the mouse main olfactory bulb". Nature 434: 470–477. doi:10.1038/nature03414.
- ^ 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 May–Jun;20(3):149-60.
- ^ Toxic chemicals linked to birth defects are being found at alarming levels in women of childbearing age
- ^ Randall Fitzgerald. The Hundred Year Lie. Dutton, 2006. p. 23. ISBN 0-525-94951-8.
- ^ "IFRA Survey:Transparency List". IFRA. Retrieved December 3, 2014.
See also
|
Look up aroma in Wiktionary, the free dictionary. |
- 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
|
Perfume
|
|
| Overview |
|
|
| Types |
- Solid perfume
- Eau de Cologne
- Eau de toilette
- Scented water
- Essential oils
- Pomander
|
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| Ingredients |
- Plant sources including Herbal distillates
- Animal sources
- Synthetic
|
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| Science |
- Aromachology
- Fragrance wheel
- Fragrance extraction
- Note
- Scentography
|
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| Professions |
|
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| Organizations |
- Fragrance Museum
- Fragrances of the World
- International Fragrance Association
- Musée du Parfum
- Osmothèque
- Research Institute of Fragrance Materials
- Théâtre-Musée des Capucines
- The Fragrance Foundation
- ISIPCA
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- Category
- Commons
- Wiktionary
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