Aroma compound

"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.

Fragrance bottles.

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 less than 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 food service industry to flavor, improve, and generally increase the appeal of their products.

An odorizer may add a detectable odor 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

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
Eucalyptol	Eucalyptus	Eucalyptus globulus

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

• 
  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. Aroma compounds can then be identified by Gas Chromatography-Olfactometry (GC-O), which involves a human operator sniffing the GC effluent.^[6]

In mammals, olfactory receptors are expressed on the surface of the olfactory epithelium in the nasal cavity.

Safety

Patch test

In 2005–06, fragrance mix was the third-most-prevalent allergen in patch tests (11.5%).^[7] 'Fragrance' was voted Allergen of the Year in 2007 by the American Contact Dermatitis Society. A recent academic study in the United States has shown that "34.7 % of the population reported health problems, such as migraine headaches and respiratory difficulties, when exposed to fragranced products".^[8]

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.^[9][10]

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.^[11]

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.^[12]

See also

Aroma compoundat Wikipedia's sister projects

• 
  Definitions from Wiktionary
  


• 
  Quotations from Wikiquote
  

• 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. 
   ^ Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst, "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a11_141.mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
   


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. PMC 3555824. PMID 23372854.
   


3. 
   ^ ^ab 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.
   


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: 470–477. doi:10.1038/nature03414. PMID 15724148.
   


6. 
   ^ Brattoli, M; Cisternino, E; Dambruoso, PR; de Gennaro, G; Giungato, P; Mazzone, A; Palmisani, J; Tutino, M (5 December 2013). "Gas chromatography analysis with olfactometric detection (GC-O) as a useful methodology for chemical characterization of odorous compounds". Sensors (Basel, Switzerland). 13 (12): 16759–800. doi:10.3390/s131216759. PMC 3892869. PMID 24316571.
   


7. 
   ^ 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.
   


8. 
   ^ Anne Steinemann, "Fragranced consumer products: exposures and effects from emissions", Air Quality, Atmosphere & Health, December 2016, Volume 9, Issue 8, pp 861–866.
   


9. 
   ^ Toxic chemicals linked to birth defects are being found at alarming levels in of childbearing age, Environmental Working Group, ewg.org. Retrieved 7 May 2018.
   


10. 
    ^ Anne C. Steinemann et al., "Fragranced Consumer Products: Chemicals Emitted, Ingredients Unlisted", Environmental Impact Assessment Review, Vol. 31, Issue 3, April 2011, pp. 328-333.
    


11. 
    ^ Randall Fitzgerald. The Hundred Year Lie. Dutton, 2006. p. 23. ISBN 0-525-94951-8.
    


12. 
    ^ "IFRA Survey:Transparency List". IFRA. Retrieved December 3, 2014.
    

v t e Perfumes
Overview	History List of perfumes
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Ingredients	Plant sources including Herbal distillates Animal sources Synthetic
Science	Aromachology Fragrance wheel Fragrance extraction Note Scentography
Professions	Aromachologist Perfumer
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 Basenotes
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