An aroma compound, also known as an odorant, aroma, fragrance or

flavoring A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gus ...

, is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

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 The olfactory system, or sense of smell, is the sensory system used for smelling ( olfaction). Olfaction is one of the special senses, that have directly associated specific organs. Most mammals and reptiles have a main olfactory system and an ...

in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds, particularly strawberries which are commercially cultivated to have appealing aromas, and contain several hundred aroma compounds. Generally, molecules meeting this specification have

molecular weight A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioch ...

s of less than 310. Flavors affect both the sense of

taste The gustatory system or sense of taste is the sensory system that is partially responsible for the perception of taste (flavor). Taste is the perception produced or stimulated when a substance in the mouth reacts chemically with taste receptor ...

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 Cosmetics are constituted mixtures of chemical compounds derived from either natural sources, or synthetically created ones. Cosmetics have various purposes. Those designed for personal care and skin care can be used to cleanse or protect ...

. Aroma compounds can naturally be found in various foods, such as fruits and their peels,

wine Wine is an alcoholic drink typically made from fermented grapes. Yeast consumes the sugar in the grapes and converts it to ethanol and carbon dioxide, releasing heat in the process. Different varieties of grapes and strains of yeasts are m ...

spices A spice is a seed, fruit, root, bark, or other plant substance primarily used for flavoring or coloring food. Spices are distinguished from herbs, which are the leaves, flowers, or stems of plants used for flavoring or as a garnish. Spices are ...

floral scent Floral scent, or flower scent, is composed of all the volatile organic compounds (VOCs), or aroma compounds, emitted by floral tissue (e.g. flower petals). Other names for floral scent include, aroma, fragrance, floral odour or perfume. Flower scen ...

perfume Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...

s, fragrance oils, and essential oils. For example, many form biochemically during the

ripening Ripening is a process in fruits that causes them to become more palatable. In general, fruit becomes sweeter, less green, and softer as it ripens. Even though the acidity of fruit increases as it ripens, the higher acidity level does not make th ...

fruit In botany, a fruit is the seed-bearing structure in flowering plants that is formed from the ovary after flowering. Fruits are the means by which flowering plants (also known as angiosperms) disseminate their seeds. Edible fruits in particu ...

s and other crops. Wines have more than 100 aromas that form as byproducts of fermentation. 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. An

odorizer An odorizer is a device that adds an odorant to a gas. The most common type is one that adds a mercaptan liquid into natural gas distribution systems so that leaks can be readily detected. Other types have been used for carbon dioxide fire ex ...

may add a detectable odor to a dangerous odorless substance, like propane,

natural gas Natural gas (also called fossil gas or simply gas) is a naturally occurring mixture of gaseous hydrocarbons consisting primarily of methane in addition to various smaller amounts of other higher alkanes. Low levels of trace gases like carbo ...

, or

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic ...

, as a safety measure.

Aroma compounds classified by structure

Esters

Linear terpenes

Cyclic terpenes

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

Aromatic

Amines

Other aroma compounds

Alcohols

Furaneol Furaneol, or strawberry furanone, is an organic compound used in the flavor and perfume industry. It is formally a derivative of furan. It is a white or colorless solid that is soluble in water and organic solvents. Odor and occurrence Althoug ...

( strawberry) *

1-Hexanol 1-Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six- carbon chain and a condensed structural formula of CH3(CH2)5OH. This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol. Two additiona ...

( herbaceous, woody) * ''cis''-3-Hexen-1-ol (fresh cut

grass Poaceae () or Gramineae () is a large and nearly ubiquitous family of monocotyledonous flowering plants commonly known as grasses. It includes the cereal grasses, bamboos and the grasses of natural grassland and species cultivated in lawns a ...

) * Menthol (

peppermint Peppermint (''Mentha'' × ''piperita'') is a hybrid species of mint, a cross between watermint and spearmint. Indigenous to Europe and the Middle East, the plant is now widely spread and cultivated in many regions of the world.Euro+Med Plantba ...

)

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

tomato The tomato is the edible berry of the plant ''Solanum lycopersicum'', commonly known as the tomato plant. The species originated in western South America, Mexico, and Central America. The Mexican Nahuatl word gave rise to the Spanish word ...

es) * Furfural (burnt

oat The oat (''Avena sativa''), sometimes called the common oat, is a species of cereal grain grown for its seed, which is known by the same name (usually in the plural, unlike other cereals and pseudocereals). While oats are suitable for human con ...

s) *

Hexyl cinnamaldehyde Hexyl cinnamaldehyde (hexyl cinnamal) is a common additive in the perfume and cosmetic industry as aroma substance. It is found naturally in the essential oil of chamomile. It is a pale yellow to yellow liquid to solid, which is nearly insoluble ...

Isovaleraldehyde Isovaleraldehyde organic compound, also known as 3-methylbutanal, with the formula (CH3)2CHCH2CHO. It is an aldehyde, a colorless liquid at STP, and found in low concentrations in many types of food. It can be produced commercially and is used as ...

– nutty, fruity, cocoa-like * Anisic aldehyde – floral, sweet, hawthorn. It is a crucial component of chocolate, vanilla, strawberry, raspberry, apricot, and others. *

Cuminaldehyde Cuminaldehyde (4-isopropylbenzaldehyde) is a natural organic compound with the molecular formula C10H12O. It is a benzaldehyde with an isopropyl group substituted in the 4-position. Cuminaldehyde is a constituent of the essential oils of eucalyp ...

(4-propan-2-ylbenzaldehyde) – Spicy, cumin-like, green

Esters

Fructone Fructone, also known as apple ketal and applinal, is a synthetic aroma compound with a fruity, apple-like smell with pineapple, strawberry, and woody aspects reminiscent of pine trees. Chemistry Fructone is usually synthesized from ethyl acet ...

(fruity, apple-like) * Ethyl methylphenylglycidate ( Strawberry) * alpha-Methylbenzyl acetate ( Gardenia)

Ketones

* Cyclopentadecanone (musk-ketone) * Dihydrojasmone (fruity woody floral) *

Oct-1-en-3-one Oct-1-en-3-one (CH2=CHC(=O)(CH2)4CH3), also known as 1-octen-3-one, is the odorant that is responsible for the typical "metallic" smell of metals and blood coming into contact with skin. Oct-1-en-3-one has a strong metallic mushroom-like odor with ...

(blood, metallic, mushroom-like) *

2-Acetyl-1-pyrroline 2-Acetyl-1-pyrroline (2AP) is an aroma compound and flavor that gives freshly baked bread, jasmine rice and basmati rice, the spice ''pandan'' (''Pandanus amaryllifolius''), and ''bread flowers'' ('' Vallaris'' ''glabra'') their customary smell. ...

(fresh bread, jasmine rice) *

6-Acetyl-2,3,4,5-tetrahydropyridine 6-Acetyl-2,3,4,5-tetrahydropyridine is an aroma compound and flavor that gives baked goods such as white bread, popcorn, and tortillas their typical smell, together with its structural homolog 2-acetyl-1-pyrroline. 6-Acetyl-2,3,4,5-tetrahydrop ...

(fresh bread, tortillas, popcorn)

Lactones

* gamma-Decalactone intense peach flavor * gamma-Nonalactone coconut odor, popular in suntan lotions * delta-Octalactone creamy note *

Jasmine lactone Jasmine lactone is a lactone and aroma compound with a powerful fatty-fruity peach and apricot flavor. Its chemical formula is C10H16O2. It occurs naturally in jasmine oil, tuberose, gardenia, mimosa, honeysuckle, lily, tea, peach, and ginger ...

powerful fatty-fruity peach and apricot *

Massoia lactone Massoia lactone is an alkyl lactone derived from the bark of the Massoia tree (''Cryptocaria massoia'') which is found in Papua, Indonesia though the compound can also be found as a component of cane sugar molasses, cured tobacco, and the essenti ...

powerful creamy coconut * Wine lactone sweet coconut odor *

Sotolon Sotolon (also known as sotolone) is a lactone and an extremely powerful aroma compound, with the typical smell of fenugreek or curry at high concentrations and maple syrup, caramel, or burnt sugar at lower concentrations. Sotolon is the major a ...

( maple syrup,

curry A curry is a dish with a sauce seasoned with spices, mainly associated with South Asian cuisine. In southern India, leaves from the curry tree may be included. There are many varieties of curry. The choice of spices for each dish in trad ...

, fenugreek)

Thiols

Thioacetone Thioacetone is an organosulfur compound belonging to the -thione group called thioketones, with a chemical formula (CH3)2CS. It is an unstable orange or brown substance that can be isolated only at low temperatures. Above , thioacetone readily co ...

(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 Garlic breath is halitosis (bad breath) resulting from the consumption of garlic. Causes The major volatile compounds responsible for garlic breath are allyl methyl sulfide, allyl methyl disulfide, allyl mercaptan, diallyl disulfide, dimethyl ...

) * (Methylthio)methanethiol (CH₃SCH₂SH), the "mouse thiol", found in mouse urine and functions as a

semiochemical A semiochemical, from the Greek wiktionary:σημεῖον, σημεῖον (''semeion''), meaning "signal", is a chemical substance or mixture released by an organism that affects the behaviors of other individuals. Semiochemical communication c ...

for female mice *

Ethanethiol Ethanethiol, commonly known as ethyl mercaptan, is an organosulfur compound with the formula CH3CH2SH. is a colorless liquid with a distinct odor. Abbreviated EtSH, it consists of an ethyl group (Et), CH3CH2, attached to a thiol group, SH. Its st ...

, 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 Methanethiol (also known as methyl mercaptan) is an organosulfur compound with the chemical formula . It is a colorless gas with a distinctive putrid smell. It is a natural substance found in the blood, brain and feces of animals (including humans ...

, commonly called methyl mercaptan (after eating

Asparagus Asparagus, or garden asparagus, folk name sparrow grass, scientific name ''Asparagus officinalis'', is a perennial flowering plant species in the genus '' Asparagus''. Its young shoots are used as a spring vegetable. It was once classified in ...

) *

Furan-2-ylmethanethiol Furan-2-ylmethanethiol (2-Furanmethanethiol) is an organic compound containing a furan substituted with a sulfanylmethyl group. It is a clear colourless liquid when pure, but it becomes yellow coloured upon prolonged standing. It possesses a stro ...

, also called furfuryl mercaptan (roasted

coffee Coffee is a drink prepared from roasted coffee beans. Darkly colored, bitter, and slightly acidic, coffee has a stimulating effect on humans, primarily due to its caffeine content. It is the most popular hot drink in the world. Seeds of ...

) * Benzyl mercaptan (leek or garlic-like)

Miscellaneous compounds

* Methylphosphine and dimethylphosphine (garlic-metallic, two of the most potent odorants known) *

Phosphine Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting ...

(

zinc phosphide Zinc phosphide ( Zn3 P2) is an inorganic chemical compound. It is a grey solid, although commercial samples are often dark or even black. It is used as a rodenticide. Zn3P2 is a II-V semiconductor with a direct band gap of 1.5 eV and may have a ...

poisoned bait) *

Diacetyl Diacetyl (IUPAC systematic name: butanedione or butane-2,3-dione) is an organic compound with the chemical formula (CH3CO)2. It is a yellow liquid with an intensely buttery flavor. It is a vicinal diketone (two C=O groups, side-by-side). Diacet ...

(

butter Butter is a dairy product made from the fat and protein components of churned cream. It is a semi-solid emulsion at room temperature, consisting of approximately 80% butterfat. It is used at room temperature as a spread, melted as a condimen ...

flavor) * Acetoin (butter flavor) * Nerolin ( orange flowers) *

Tetrahydrothiophene Tetrahydrothiophene is an organosulfur compound with the formula (CH2)4S. The molecule consists of a five-membered saturated ring with four methylene groups and a sulfur atom. It is the saturated analog of thiophene. It is a volatile, colorles ...

(added to

) *

2,4,6-Trichloroanisole 2,4,6-Trichloroanisole (TCA) is a chemical compound that is a chlorinated derivative of anisole. TCA is a fungal metabolite of 2,4,6-trichlorophenol, which is used as a fungicide. It can be found in minute traces on packaging materials stored in ...

(

cork taint Cork taint is a broad term referring to a wine fault characterized by a set of undesirable smells or tastes found in a bottle of wine, especially spoilage that can only be detected after bottling, aging and opening. Though modern studies have sho ...

) * Substituted

pyrazine Pyrazine is a heterocyclic aromatic organic compound with the chemical formula C4H4N2. It is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. It is a ''"deliquescent crystal or wax-li ...

Aroma-compound receptors

Animals that are capable of smell detect aroma compounds with their

olfactory receptor Olfactory receptors (ORs), also known as odorant receptors, are chemoreceptors expressed in the cell membranes of olfactory receptor neurons and are responsible for the detection of odorants (for example, compounds that have an odor) which give r ...

s. Olfactory receptors are cell-membrane

receptors Receptor may refer to: *Sensory receptor, in physiology, any structure which, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and responds to a n ...

on the surface of

sensory neurons Sensory neurons, also known as afferent neurons, are neurons in the nervous system, that convert a specific type of stimulus, via their receptors, into action potentials or graded potentials. This process is called sensory transduction. The ...

in the

that detect airborne aroma compounds. Aroma compounds can then be identified by gas chromatography-olfactometry, which involves a human operator sniffing the GC effluent. In mammals, olfactory receptors are expressed on the surface of the olfactory epithelium in the

nasal cavity The nasal cavity is a large, air-filled space above and behind the human nose, nose in the middle of the face. The nasal septum divides the cavity into two cavities, also known as fossae. Each cavity is the continuation of one of the two nostrils. ...

Safety and regulation

In 2005–06, fragrance mix was the third-most-prevalent

allergen An allergen is a type of antigen that produces an abnormally vigorous immune response in which the immune system fights off a perceived threat that would otherwise be harmless to the body. Such reactions are called allergies. In technical terms ...

in patch tests (11.5%). '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". 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. In the United States, this is because the law regulating cosmetics protects

trade secret Trade secrets are a type of intellectual property that includes formulas, practices, processes, designs, instruments, patterns, or compilations of information that have inherent economic value because they are not generally known or readily ...

s.Fragrances in Cosmetics
/ref> In the United States, fragrances are regulated by the

Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respon ...

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 The Toxic Substances Control Act (TSCA) is a United States law, passed by the 94th United States Congress in 1976 and administered by the United States Environmental Protection Agency (EPA), that regulates chemicals not regulated by other U.S. ...

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 Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it be ...

. The EPA, however, does not conduct independent safety testing but relies on data provided by the manufacturer. A 2019 study of the top-selling skin moisturizers found 45% of those marketed as "fragrance-free" contained fragrance.

List of chemicals used as fragrances

In 2010, the

International Fragrance Association The International Fragrance Association (IFRA) is the global representative body of the fragrance industry. It seeks to represent the collective interests of the industry and promote the safe use of fragrances through regulation. The Association wa ...

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.

References

{{DEFAULTSORT:Aroma Compound Organic chemistry Olfaction Flavors Perfume ingredients

Aroma compounds classified by structure

Esters

Linear terpenes

Cyclic terpenes

Aromatic

Amines

Other aroma compounds

Alcohols

Aldehydes

Esters

Ketones

Lactones

Thiols

Miscellaneous compounds

Aroma-compound receptors

Safety and regulation

List of chemicals used as fragrances

See also

References