Aroma compound explained

Aroma compound should not be confused with Aromatic compound.

An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently volatile for transmission via the air to the olfactory system in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds,[1] particularly strawberries which are commercially cultivated to have appealing aromas, and contain several hundred aroma compounds.[1] [2]

Generally, molecules meeting this specification have molecular weights of less than 310.[3] Flavors affect both the sense of taste and smell, whereas fragrances affect only smell. Flavors tend to be naturally occurring, and the term fragrances may also apply to synthetic compounds, such as those used in cosmetics.

Aroma compounds can naturally be found in various foods, such as fruits and their peels, wine, spices, floral scent, perfumes, fragrance oils, and essential oils. For example, many form biochemically during the ripening of fruits and other crops.[1] [4] Wines have more than 100 aromas that form as byproducts of fermentation.[5] 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]

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

Aroma compounds classified by structure

Esters

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, Strawberry
Methyl anthranilateFruityGrape
Methyl salicylateMinty, root beerWintergreen
Hexyl acetateFloral, FruityApple, Plum

Linear terpenes

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

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

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

Aromatic

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

Amines

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

Alcohols

Aldehydes

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

Esters

Ketones

Lactones

Thiols

See main article: Thiol.

Miscellaneous compounds

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, which involves a human operator sniffing the GC effluent.[10]

In mammals, olfactory receptors are expressed on the surface of the olfactory epithelium in the nasal cavity.[4]

Safety and regulation

In 2005–06, fragrance mix was the third-most-prevalent allergen in patch tests (11.5%).[11] 'Fragrance' was voted Allergen 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".[12]

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.[13] In the United States, this is because the law regulating cosmetics protects trade secrets.[14]

In the United States, fragrances are regulated by the Food and Drug Administration if present in cosmetics or drugs, by the Consumer Products Safety Commission if present in consumer products. No pre-market approval is required, except for drugs. Fragrances are also generally regulated 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.[15]

A 2019 study of the top-selling skin moisturizers found 45% of those marketed as "fragrance-free" contained fragrance.[16]

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, identifying about 90% of the world's production volume of fragrances.[17]

See also

References

  1. El Hadi . Muna . Zhang . Feng-Jie . Wu . Fei-Fei . Zhou . Chun-Hua . Tao . Jun . Advances in fruit aroma volatile research . Molecules . 18 . 7 . 2013-07-11 . 1420-3049 . 23852166 . 6270112 . 10.3390/molecules18078200 . 8200–8229. free .
  2. Ulrich . Detlef . Kecke . Steffen . Olbricht . Klaus . What do we know about the chemistry of strawberry aroma? . Journal of Agricultural and Food Chemistry . 66 . 13 . 2018-03-13 . 0021-8561 . 29533612 . 10.1021/acs.jafc.8b01115 . 3291–3301.
  3. Rothe . M . Specht . M . [Notes about molecular weights of aroma compounds] ]. Nahrung . 1976 . 20 . 3 . 281–6 . 10.1002/food.19760200308 . 958345 . 29 September 2020.
  4. Haugeneder . Annika . Trinkl . Johanna . Härtl . Katja . Hoffmann . Thomas . Allwood . James William . Schwab . Wilfried . Answering biological questions by analysis of the strawberry metabolome . Metabolomics. 14 . 11 . 2018-10-26 . 1573-3882 . 30830391 . 6394451 . 10.1007/s11306-018-1441-x . 145.
  5. Ilc . Tina . Werck-Reichhart . Danièle . Navrot . Nicolas . Meta-analysis of the core aroma components of grape and wine aroma . Frontiers in Plant Science. 7 . 2016-09-30 . 1472 . 1664-462X . 27746799 . 5042961 . 10.3389/fpls.2016.01472. free .
  6. 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 . 10.1371/journal.pone.0055780 . 23372854 . 3555824. 2013PLoSO...855780G . free .
  7. Book: Block, E. . Garlic and Other Alliums: The Lore and the Science . Royal Society of Chemistry . 2010 . 978-0-85404-190-9 .
  8. Lin . D.Y. . Zhang . S.Z. . Block . E. . Katz . L.C. . 162036 . 2005 . Encoding social signals in the mouse main olfactory bulb . Nature . 434 . 7032. 470–477 . 10.1038/nature03414 . 15724148. 2005Natur.434..470L .
  9. Glindemann, D.. Dietrich, A.. Staerk, H.. Kuschk, P.. The Two Odors of Iron when Touched or Pickled: (Skin) Carbonyl Compounds and Organophosphines. Angewandte Chemie International Edition. 2005. 45. 42. 7006–7009. 10.1002/anie.200602100. 17009284.
  10. Brattoli . M . Cisternino . E . Dambruoso . PR . de Gennaro . G . Giungato . P . Mazzone . A . Palmisani . J . Tutino . M . Gas chromatography analysis with olfactometric detection (GC-O) as a useful methodology for chemical characterization of odorous compounds. . Sensors (Basel, Switzerland) . 5 December 2013 . 13 . 12 . 16759–800 . 10.3390/s131216759 . 24316571 . 3892869. 2013Senso..1316759B . free .
  11. 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 . 2162-5220 . 19470301.
  12. [Anne C. Steinemann|Anne Steinemann]
  13. 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.
  14. https://www.fda.gov/cosmetics/cosmetic-ingredients/fragrances-cosmetics Fragrances in Cosmetics
  15. Book: Randall Fitzgerald . Randall Fitzgerald . The Hundred Year Lie. Dutton, 2006 . 23 . 978-0-525-94951-0. The Hundred Year Lie . 2006 .
  16. Web site: 'Hypoallergenic' And 'Fragrance-Free' Moisturizer Claims Are Often False. Patti Neighmond. NPR. 2 October 2017.
  17. Web site: IFRA Survey:Transparency List . IFRA. December 3, 2014.