Fragrance compound
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A fragrance compound (or fragrance) is a chemical compound with a pleasant odor. Fragrances affect only the sense of smell, whereas flavors can affect both the sense of taste and smell. Fragrances are often mixtures of individual fragrance compounds. Although many fragrances are derived from natural sources, many are synthetic. Fragrances are widely used in cosmetics and are the basis for a large industry.[2]
Related odiferous compounds
Stench compounds have unpleasant odors. Some are used as odorizer or an odorant usually have an intense odor, which may be pleasant or not. They are sometimes used to confer a detectable odor to an odorless substance, like propane, natural gas, or hydrogen, as a safety measure.[3]
Occurrence
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. Generally, fragrance compounds have molecular weights of less than 310.[4]
Fragrance compounds are found in various foods, such as fruits and their peels, wine, spices, floral scent, perfumes, fragrance oils, and essential oils. For example, many form during the ripening of fruits and other crops.[5] Wines have more than 100 aromas that form as byproducts of fermentation.[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.[2]
History, biochemistry, economics
The technology of fragrances came with the invention of distillation, which allowed to be concentrated and sometimes even separated into individual components. The purification of cinnamaldehyde, the first single component fragrance, marked the beginning of the fragrance and flavor industries. Other single component fragrance compounds that were purified in the 19th century include benzaldehyde, methyl salicylate (oil of wintergreen), and vanillin. Somewhat in step with the synthetic dye industry, the fragrance and flavor industry was established. Many fragrance compounds were prepared synthetically. Spectroscopic methods coupled with various separation techniques allowed the identification of traces of aroma compounds (e.g. in wines, flower extracts, etc.).[2] Tetramethyl acetyloctahydronaphthalenes have been described as "the most successful synthetic fragrance".[7]
The invention of gas chromatography was very important to the development of fragrances.[8] Gas chromatography-olfactometry sometimes involving a human operator sniffing the GC effluent is particularly relevant to the analysis of fragrances.[9] GC-O and related techniques have also been developed to characterize individual enantiomers of chiral aromatic compounds.
Studies on synthetic musk reveal that the odors of some compounds are noticeably affected by deuteration.[10]
Various fragrant fruits are commercially cultivated to have appealing or intensified aromas.[11]
Fragrance compounds classified by chemical structure
Script error: No such module "Labelled list hatnote". 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.[12][13]
Esters
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 |
Coriander, Sweet basil, Lavender, Honeysuckle | |
| Nerolidol | Woody, fresh bark | Neroli, ginger Jasmine |
|
| Ocimene | Fruity, Floral | Mango, Curcuma amada |
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 | |
| Jasmone | spicy, fruity, floral in dilution | Jasmine, Honeysuckle |
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 |
Other aroma compounds
Alcohols
- Furaneol (strawberry)
- 1-Hexanol (herbaceous, woody)
- cis-3-Hexen-1-ol (fresh cut grass)
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 – Spicy, cumin-like, green
Ketones
- Dihydrojasmone (fruity woody floral)
- Oct-1-en-3-one (blood, metallic, mushroom-like)[14]
- 2-Acetyl-1-pyrroline (fresh bread, jasmine rice)
- 6-Acetyl-2,3,4,5-tetrahydropyridine (fresh bread, tortillas, popcorn)
- Diacetyl (butter flavor)
- Acetoin (butter flavor)
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)
Detection and interpretation
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Fragrances are detected by the nose when the movement of inspired air contacts olfactory sensory neurons, which in humans, number between 6 and 10 million over a surface area of Template:Cvt of olfactory epithelium.[15] Fragrance signals are conveyed from the epithelium to the olfactory nerves, and then to the olfactory bulbs, which relay neural impulses about fragrance properties into the primary olfactory cortex of the brain.[15] In the olfactory cortex, fragrance characteristics are integrated to evaluate the safety and appeal of compounds to be ingested, and to recognize environmental and social factors associated by memory with the fragrance.[15][16]
Safety and regulation
In 2005–06, fragrance mix was the third-most-prevalent allergen in patch tests (11.5%).[17] '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".[18]
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.[19] In the United States, this is because the law regulating cosmetics protects trade secrets.[20]
In the United States, fragrances are regulated by the Food and Drug Administration if present in cosmetics or drugs, by the Consumer Product Safety Commission if present in consumer products.[20] 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.[21]
A 2019 study of the top-selling skin moisturizers found 45% of those marketed as "fragrance-free" contained fragrance.[22]
See also
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- Aroma of wine
- Eau de toilette
- Flavour and Fragrance Journal
- Fragrances of the World
- Foodpairing
- Odor
- Odor detection threshold
- Odorizer, a device for adding an odorant to gas flowing through a pipe
- Olfaction
- Olfactory receptor
- Olfactory system
- Pheromone
- The Hundred Year Lie
- Vabbing
References
- ^ Page Module:Citation/CS1/styles.css has no content.Buettner A.; Schieberle P. (1999). "Characterization of the Most Odor-Active Volatiles in Fresh, Hand-Squeezed Juice of Grapefruit (Citrus paradisi Macfayden)". J. Agric. Food Chem. 47 (12): 5189–5193. Bibcode:1999JAFC...47.5189B. doi:10.1021/jf990071l. PMID 10606593.
- ^ a b c Page Module:Citation/CS1/styles.css has no content.Panten, Johannes; Surburg, Horst (2015). "Flavors and Fragrances, 1. General Aspects". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–9. doi:10.1002/14356007.a11_141.pub2. ISBN 978-3-527-30673-2.
- ^ Page Module:Citation/CS1/styles.css has no content.Mouli-Castillo, Julien; Bartlett, Sam; Murugan, Arul; Badham, Pete; Wrynne, Aidan; Haszeldine, Stuart; Wheeldon, Mark; McIntosh, Angus (April 14, 2020). "Olfactory appraisal of odorants for 100% hydrogen networks". International Journal of Hydrogen Energy. 45 (20): 11875–11884. Bibcode:2020IJHE...4511875M. doi:10.1016/j.ijhydene.2020.02.095. ISSN 0360-3199.
- ^ Page Module:Citation/CS1/styles.css has no content.Rothe, M; Specht, M (1976). "[Notes about molecular weights of aroma compounds]". Nahrung. 20 (3): 281–6. doi:10.1002/food.19760200308. PMID 958345.
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