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.

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.

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.

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)
• Dihydrojasmone (fruity woody floral)
• Oct-1-en-3-one (blood, metallic, mushroom-like)
• 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)
• (Methylthio)methanethiol (CH₃SCH₂SH), the "mouse thiol", found in mouse urine and functions as a semiochemical for female mice
• 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)
• 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

Patch test

In 2005–06, fragrance mix was the third-most-prevalent allergen in patch tests (11.5%).

'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.

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.

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.

See also

• 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