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Aroma compound

From Wikipedia, the free encyclopedia
(Redirected fromFragrances)
Chemical compound that has a smell or odor
Several terms redirect here. For other uses, seeFragrance (disambiguation), Fragrant, Kentucky, and The Odorants.
Not to be confused withAromatic compound.

Fragrance bottles

Anaroma compound, also known as anodorant,aroma,fragrance,flavoring orflavor, is achemical compound that has a smell orodor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficientlyvolatile for transmission via the air to theolfactory system in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds,[1] particularly strawberries which arecommercially cultivated to have appealing aromas, and contain several hundred aroma compounds.[1][2]

Generally, molecules meeting this specification havemolecular weights of less than 310.[3] Flavors affect both the sense oftaste andsmell, whereas fragrances affect only smell. Flavors tend to be naturally occurring, and the termfragrances may also apply to synthetic compounds, such as those used incosmetics.[4]

Aroma compounds can naturally be found in variousfoods, such as fruits and theirpeels,wine,spices,floral scent,perfumes,fragrance oils, andessential oils. For example, many formbiochemically during theripening offruits and other crops.[1][5] Wines have more than 100 aromas that form as byproducts offermentation.[6] Also, many of the aroma compounds play a significant role in the production of compounds used in the food service industry to flavor, improve, and generally increase the appeal of their products.[1]

Anodorizer may add a detectable odor to a dangerous odorless substance, likepropane,natural gas, orhydrogen, as a safety measure.

Aroma compounds classified by structure

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Esters

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Compound nameFragranceNatural occurrenceChemical structure
Geranyl acetateFruity,
Floral
Rose
Methyl formateEthereal
Methyl acetateSweet, nail polish
Solvent
Methyl propionate
Methyl propanoate
Sweet, fruity,rum-like
Methyl butyrate
Methyl butanoate
FruityApple
Pineapple
Ethyl acetateSweet, solventWine
Ethyl butyrate
Ethyl butanoate
FruityOrange,Pineapple
Isoamyl acetateFruity,Banana,
Pear
Banana plant
Pentyl butyrate
Pentyl butanoate
FruityPear
Apricot
Pentyl pentanoateFruityApple
Octyl acetateFruityOrange
Benzyl acetateFruity,StrawberryStrawberries
Methyl anthranilateFruityGrape
Methyl salicylateMinty,root beerWintergreen
Hexyl acetateFloral, FruityApple,Plum

Linear terpenes

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Compound nameFragranceNatural occurrenceChemical structure
MyrceneWoody, complexVerbena,Bay leaf
GeraniolRose, floweryGeranium,Lemon
NerolSweet rose, floweryNeroli,Lemongrass
Citral, lemonal
Geranial, neral
LemonLemon myrtle,Lemongrass
CitronellalLemonLemongrass
CitronellolLemonLemongrass,rose
Pelargonium
LinaloolFloral, sweet
Woody
Coriander,Sweet basil,Lavender,Honeysuckle
NerolidolWoody, fresh barkNeroli,ginger
Jasmine
OcimeneFruity, FloralMango,Curcuma amada

Cyclic terpenes

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Compound nameFragranceNatural occurrenceChemical structure
LimoneneOrangeOrange,lemon
CamphorCamphorCamphor laurel
MentholMentholMentha
Carvone1Caraway orSpearmintCaraway,dill,
spearmint
TerpineolLilacLilac,cajuput
alpha-IononeViolet, woodyViolet
ThujoneMintyWormwood,lilac,
juniper
EucalyptolEucalyptusEucalyptus
Jasmonespicy, fruity, floral in dilutionJasmine,Honeysuckle

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

Aromatic

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Compound nameFragranceNatural occurrenceChemical structure
BenzaldehydeAlmondBitter almond
EugenolCloveClove
CinnamaldehydeCinnamonCassia
Cinnamon
Ethyl maltolCooked fruit
Caramelized sugar
VanillinVanillaVanilla
AnisoleAniseAnise
AnetholeAniseAnise
Sweet basil
EstragoleTarragonTarragon
ThymolThymeThyme

Amines

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Compound nameFragranceNatural occurrenceChemical structure
TrimethylamineFishy
Ammonia
Putrescine
Diaminobutane
Rotting fleshRotting flesh
CadaverineRotting fleshRotting flesh
PyridineFishyBelladonna
IndoleFecal
Flowery
Feces
Jasmine
SkatoleFecal
Flowery
Feces
(diluted) Orange Blossoms

Other aroma compounds

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Alcohols

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Aldehydes

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

Esters

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Ketones

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Lactones

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Thiols

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Main article:Thiol

Miscellaneous compounds

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Aroma-compound receptors

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Animals that are capable ofsmell detect aroma compounds with theirolfactory receptors. Olfactory receptors are cell-membranereceptors on the surface ofsensory neurons in theolfactory system that detect airborne aroma compounds. Aroma compounds can then be identified bygas chromatography-olfactometry, which involves a human operator sniffing the GC effluent.[11]

Inmammals, olfactory receptors areexpressed on the surface of the olfactory epithelium in thenasal cavity.[5]

Safety and regulation

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Patch test

In 2005–06, fragrance mix was the third-most-prevalentallergen inpatch tests (11.5%).[12] 'Fragrance' was votedAllergen of the Year in 2007 by the American Contact Dermatitis Society. An academic study in the United States published in 2016 has shown that "34.7 % of the population reported health problems, such as migraine headaches and respiratory difficulties, when exposed to fragranced products".[13]

The composition of fragrances is usually not disclosed in the label of the products, hiding the actual chemicals of the formula, which raises concerns among some consumers.[14] In the United States, this is because the law regulating cosmetics protectstrade secrets.[15]

In the United States, fragrances are regulated by theFood and Drug Administration if present in cosmetics or drugs, by theConsumer Products Safety Commission if present in consumer products.[15] No pre-market approval is required, except for drugs. Fragrances are also generally regulated by theToxic 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 theEPA. The EPA, however, does not conduct independent safety testing but relies on data provided by the manufacturer.[16]

A 2019 study of the top-sellingskin moisturizers found 45% of those marketed as "fragrance-free" contained fragrance.[17]

List of chemicals used as fragrances

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In 2010, theInternational Fragrance Association published a list of 3,059 chemicals used in 2011 based on a voluntary survey of its members, identifying about 90% of the world's production volume of fragrances.[18]

See also

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References

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  1. ^abcdEl Hadi, Muna; Zhang, Feng-Jie; Wu, Fei-Fei; Zhou, Chun-Hua; Tao, Jun (July 11, 2013)."Advances in fruit aroma volatile research".Molecules.18 (7):8200–8229.doi:10.3390/molecules18078200.ISSN 1420-3049.PMC 6270112.PMID 23852166.
  2. ^Ulrich, Detlef; Kecke, Steffen; Olbricht, Klaus (March 13, 2018). "What do we know about the chemistry of strawberry aroma?".Journal of Agricultural and Food Chemistry.66 (13):3291–3301.doi:10.1021/acs.jafc.8b01115.ISSN 0021-8561.PMID 29533612.
  3. ^Rothe, M; Specht, M (1976)."[Notes about molecular weights of aroma compounds]".Nahrung.20 (3):281–6.doi:10.1002/food.19760200308.PMID 958345. RetrievedSeptember 29, 2020.
  4. ^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.ISBN 978-3-527-30673-2.
  5. ^abHaugeneder, Annika; Trinkl, Johanna; Härtl, Katja; Hoffmann, Thomas; Allwood, James William; Schwab, Wilfried (October 26, 2018)."Answering biological questions by analysis of the strawberry metabolome".Metabolomics.14 (11): 145.doi:10.1007/s11306-018-1441-x.ISSN 1573-3882.PMC 6394451.PMID 30830391.
  6. ^Ilc, Tina; Werck-Reichhart, Danièle; Navrot, Nicolas (September 30, 2016)."Meta-analysis of the core aroma components of grape and wine aroma".Frontiers in Plant Science.7: 1472.doi:10.3389/fpls.2016.01472.ISSN 1664-462X.PMC 5042961.PMID 27746799.
  7. ^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 (1): e55780.Bibcode:2013PLoSO...855780G.doi:10.1371/journal.pone.0055780.PMC 3555824.PMID 23372854.
  8. ^abGlindemann, 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.
  9. ^Block, E. (2010).Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry.ISBN 978-0-85404-190-9.
  10. ^Lin, D.Y.; Zhang, S.Z.; Block, E.; Katz, L.C. (2005). "Encoding social signals in the mouse main olfactory bulb".Nature.434 (7032):470–477.Bibcode:2005Natur.434..470L.doi:10.1038/nature03414.PMID 15724148.S2CID 162036.
  11. ^Brattoli, M; Cisternino, E; Dambruoso, PR; de Gennaro, G; Giungato, P; Mazzone, A; Palmisani, J; Tutino, M (December 5, 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.Bibcode:2013Senso..1316759B.doi:10.3390/s131216759.PMC 3892869.PMID 24316571.
  12. ^Zug, Kathryn A.; Warshaw, Erin M.; Fowler, Joseph F.; Maibach, Howard I.; Belsito, Donald L.; Pratt, Melanie D.; Sasseville, Denis; Storrs, Frances J.; Taylor, James S.; Mathias, C. G. Toby; Deleo, Vincent A.; Rietschel, Robert L.; Marks, James (2009)."Patch-test results of the North American Contact Dermatitis Group 2005-2006".Dermatitis: Contact, Atopic, Occupational, Drug.20 (3):149–160.ISSN 2162-5220.PMID 19470301.
  13. ^Anne Steinemann,"Fragranced consumer products: exposures and effects from emissions",Air Quality, Atmosphere & Health, December 2016, Volume 9, Issue 8, pp 861–866.
  14. ^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.
  15. ^abFragrances in Cosmetics
  16. ^Randall Fitzgerald (2006).The Hundred Year Lie.Dutton, 2006. p. 23.ISBN 978-0-525-94951-0.
  17. ^Patti Neighmond (October 2, 2017)."'Hypoallergenic' And 'Fragrance-Free' Moisturizer Claims Are Often False". NPR.
  18. ^"IFRA Survey:Transparency List".IFRA. RetrievedDecember 3, 2014.
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