Decenoic acid is any mono-

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

with an unbranched chain of ten carbons connected by eight single bonds and one

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

; that 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 ...

with formula ––––H, where ''k'' is between 0 and 7 inclusive. There are fifteen of these compounds, that can be identified by the position ''k''+2 of the double bond and (for ''k'' ≤ 6) the

configuration Configuration or configurations may refer to: Computing * Computer configuration or system configuration * Configuration file, a software file used to configure the initial settings for a computer program * Configurator, also known as choice board ...

(''cis'' or ''trans'') of the single bonds adjacent to it. Decenoic acids are technically mono-unsaturated

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...

s (with code C10:1), although they are relatively rare in nature.

Examples

Free acids and esters

Some isomers (and esters thereof) that have received attention are * ''cis''-2-decenoic acid or (2''Z'')-dec-2-enoic acid. (CAS 15790-91-7, Nikkaji J1.577.978K) Produced by ''

Pseudomonas aeruginosa ''Pseudomonas aeruginosa'' is a common encapsulated, gram-negative, aerobic–facultatively anaerobic, rod-shaped bacterium that can cause disease in plants and animals, including humans. A species of considerable medical importance, ''P. aerugi ...

'', inhibits biofilm formation. * ''trans''-2-decenoic acid or (2''E'')-dec-2-enoic acid. Flavoring agent (CAS 334-49-6, Nikkaji J98.042K,

FEMA The Federal Emergency Management Agency (FEMA) is an agency of the United States Department of Homeland Security (DHS), initially created under President Jimmy Carter by Presidential Reorganization Plan No. 3 of 1978 and implemented by two Exec ...

3913,

JECFA The Joint FAO/WHO Expert Committee on Food Additives (JECFA) is an international scientific expert committee that is administered jointly by the Food and Agriculture Organization of the United Nations (FAO) and the World Health Organization (WHO). ...

1372, FDA 332T8TH7B1); Density: 0.92-0.93 25 °C. Refractive Index: ~1.46 at 20.00 °C. MP: 12 °C BP: 161-162 °C. at 15.00 torr, 278-279 °C. at 1 atm. Odor described as "fresh, fruity (peach), slightly oily and waxy". Stimulates nerve cell regeneration and biofilm disintegration. Excreted by the

caries Tooth decay, also known as cavities or caries, is the breakdown of teeth due to acids produced by bacteria. The cavities may be a number of different colors from yellow to black. Symptoms may include pain and difficulty with eating. Complicatio ...

bacterium ''

Streptococcus mutans ''Streptococcus mutans'' is a facultatively anaerobic, gram-positive coccus (round bacterium) commonly found in the human oral cavity and is a significant contributor to tooth decay. It is part of the " streptococci" (plural, non-italic lowercase ...

'' and inhibits growth of the fungus ''

Candida albicans ''Candida albicans'' is an opportunistic pathogenic yeast that is a common member of the human gut flora. It can also survive outside the human body. It is detected in the gastrointestinal tract and mouth in 40–60% of healthy adults. It is us ...

''. ** ethyl trans-2-decenoate (CAS 7367-88-6, Pubchem 5463904, 6047581, Nikkaji J212.367C, J1.075.382A, FDA B2K05S6L5Q, JECFA 1814, FEMA 3641) Flavoring agent. BP: ~134 °C. at 20.00 torr, 140 °C. at 30.00 torr. Odor described as "green, fruity (apple, pear), waxy." "peely citrus". * ''cis''-3-decenoic acid or (3''Z'')-dec-3-enoic acid. (CAS 2430-93-5, Nikkaji J3.028G) The female sex

pheromone A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavio ...

of the furniture carpet beetle ''

Anthrenus flavipes ''Anthrenus flavipes'' is a species of beetle in the family Dermestidae known by the common name furniture carpet beetle. It has a cosmopolitan distribution, occurring throughout the world, being most active in warmer climates.Gahlhoff, J. EFurn ...

''. Odor deascribed as "fatty". * trans-3-decenoic acid (CAS 53678-20-9, Beilstein 1722688, Pubchem 5282725, Nikkaji J98.043I) Occurs in some natural extracts. * ''cis''-4-decenoic acid or (4''Z'')-dec-4-enoic acid. (CAS 505-90-8, Pubchem 5312351, Nikkaji J79.643C, FDA 6PR4L1KTAZ) A metabolite found in human

plasma Plasma or plasm may refer to: Science * Plasma (physics), one of the four fundamental states of matter * Plasma (mineral), a green translucent silica mineral * Quark–gluon plasma, a state of matter in quantum chromodynamics Biology * Blood pla ...

in certain

pathologies Pathology is the study of the causes and effects of disease or injury. The word ''pathology'' also refers to the study of disease in general, incorporating a wide range of biology research fields and medical practices. However, when used in t ...

. Odor described as "fatty, green". ** ethyl cis-4-decenoate (CAS 7367-84-2, Pubchem 5463488, Nikkaji J212.366E) Flavoring agent. Density: 0.883 at 20 °C. Refractive Index: 1.438 at 20 °C. BP: 128 °C. at 30 torr, 236-237 °C. at 1 atm. * ''trans''-4-decenoic acid or (4''E'')-dec-4-enoic acid. (CAS 57602-94-5, Pubchem 5282726, Nikkaji J98.044G, FDA S0TXC5QGPU) Result of reacting 1‐octene and

manganese(III) acetate Manganese(III) acetate describes a family of materials with the approximate formula Mn(O2CCH3)3. These materials are brown solids that are soluble in acetic acid and water. They are used in organic synthesis as oxidizing agents. Structure Altho ...

. **

ethyl trans-4-decenoate Ethyl may refer to: Arts and entertainment * Cold Ethyl, a Swedish rock band *Ethyl Sinclair, a character in the ''Dinosaurs'' television show Science and technology * Ethyl group, an organic chemistry moiety * Ethyl alcohol (or ethanol) * Et ...

(CAS 76649-16-6, Pubchem 5362583, Nikkaji J208.443K, FDA 3I89X5937N, JECFA 341, FEMA 3642) Density: ~0.876 at 25.00 °C. Refractive Index: ~1.437 at 20.00 °C. BP: 72.00 °C. at 0.10 torr. Odor described as "green, fruity (pineapple, apple), waxy, cognac". * cis-5-decenoic acid (CAS 84168-28-5, Pubchem 15101542, Nikkaji J2.261.052J, FDA 5R82Y8PAHS) Odor described as "fatty, green". * trans-5-decenoic acid (CAS 16424-55-8, Nikkaji J2.261.051A, Pubchem 5362593, FDA P9YWE0K08Y) Odor described as "milky, fatty". * caproleic acid, 9-decenoic acid, or dec-9-enoic acid. (CAS 14436-32-9, PUBchem 61743, FEMA 3660, Nikkaji J81.770H, FDA U2E27P3TGK) Small amounts in

goat The goat or domestic goat (''Capra hircus'') is a domesticated species of goat-antelope typically kept as livestock. It was domesticated from the wild goat (''C. aegagrus'') of Southwest Asia and Eastern Europe. The goat is a member of the a ...

and

cow milk Milk is a white liquid food produced by the mammary glands of mammals. It is the primary source of nutrition for young mammals (including breastfed human infants) before they are able to digest solid food. Immune factors and immune-modulating ...

, and oils of ''

Sapium sebiferum ''Triadica sebifera'' is a tree native to eastern China. It is commonly called Chinese tallow, Chinese tallowtree, Florida aspen, chicken tree, gray popcorn tree, or candleberry tree. The seeds (as well as from those of '' Triadica cochinchine ...

'' and ''

Litsea cubeba ''Litsea cubeba'', the aromatic litsea or may chang, is an evergreen tree or shrub 5–12 meters high in the family Lauraceae. It is native to Southern Chinese region including Sichuan, Guizhou, Yunnan, Taiwan and Fujian, and Southeast Asian co ...

''. Traces also in beer, wine, clams, Parmesan cheese and snails. Broad-spectrum antimicrobial. Flavoring agent (FEMA 3660, JECFA 328). Density: ~0.9 at 20.00 °C. BP: ~270 °C at 1 atm, 130-135 °C at 1-3

torr The torr (symbol: Torr) is a unit of pressure based on an absolute scale, defined as exactly of a standard atmosphere (). Thus one torr is exactly (≈ ). Historically, one torr was intended to be the same as one "millimeter of mercury ...

, 95 °C at 0.1 torr. Refractive index n_D²⁰: 1.4488. Irritating to skin. Used as flavouring agent. Odor described as milky,waxy,green,fatty,soapy,creamy,cheesy". ** ethyl caproleate, 9-decenoic acid ethyl ester (CAS 67233-91-4, Pubchem 522255, Nikkaji J976.137C, FDA OI02K838CN) used as flavoring agent. Odor described as "fruity". Density: ~0.878 at 25.00 °C. Refractive Index: ~1.44 at 20.00 °C. BP: 249-250 °C. at 1 atm.

Unspecified isomers and mixtures

The following unspecified isomers or mixtures have also been mentioned: * From 3-decenoic acid: ** butyl 2-decenoate, isomer unspecified (CAS 7492-45-7, Pubchem 5463906, Nikkaji J421.861B, FDA 38KP1S005I, JECFA 1348, FEMA 2194), is a flavoring agent with odor described as "fruity (peach, apricot), green, fatty, coconut, walnut". Density: 0.87-0.88 at 25.00 °C. Refractive Index: ~1.45 at 20.00 °C. BP: 290-291 °C. at 1 atm. Flavouring agent. ** methyl 2-decenoate, isomer unspecified (CAS 2482-39-5, Pubchem 5368064, Nikkaji J110.937E, FDA 7YEW204WFW), is used as flavouring ingredient, with odor described as "mushroom". * 4-decenoic acid, unspecified isomer (CAS 26303-90-2, Nikkaji J39.562E, FDA S0TXC5QGPU, JECFA 1287, FEMA 3914), is said to occur in hops and beer. It is a flavoring agent, with odor described as "fruity". Density: ~0.92 at 20.00 °C. Refractive Index: ~1.15 at 20.00 °C. BP: 97.00 to 98.00 °C. at 0.30 torr. It is listed as "no concern" food additive (FEMA 3914, JECFA 1287) by the FAO/WHO JECFA. * A mixture of 5-decenoic and 6-decenoic acids (JECFA 327, FDA 8H370297TA), with the trade name "milk lactone", is allowed in the US as Generally Recognized as Safe (GRAS)

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 gusta ...

s, such as in imitation dairy products with common name "milk lactone" for their milk-like aroma.

Derivatives

Derivatives of these acids include: * 4-Hydroxy-4-methyl-''cis''-7-decenoic acid. Its gamma

lactone Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the co ...

is a flavoring agent (FEMA 3937, JECFA 1159). * 5-hydroxy-7-decenoic acid. Its

was identified as a significant component of the aroma of

black tea Black tea, also translated to red tea in various East Asian languages, is a type of tea that is more oxidized than oolong, yellow, white and green teas. Black tea is generally stronger in flavour than other teas. All five types are made from ...

, reminiscent of flowers and dried fruit, and is a flavoring agent (FEMA 3745, JECFA 247). * 9-hydroxy-''trans''-2-decenoic acid. Another queen bee pheromone. * 9-oxo-''cis''-2-decenoic acid. Is converted to the ''trans'' isomer by light and may function as inhibitor of bee colony settlement. * 9-oxo-''trans''-2-decenoic acid.A pheromone produced by queen bees. * 10-hydroxy-''trans''-2-decenoic acid, "queen bee acid" (CAS 14113-05-4, Pubchem 5312738, Nikkaji J838.856C, FDA 76B519G7TJ). The main fatty acid in

bee Bees are winged insects closely related to wasps and ants, known for their roles in pollination and, in the case of the best-known bee species, the western honey bee, for producing honey. Bees are a monophyly, monophyletic lineage within the ...

royal jelly Royal jelly is a honey bee secretion that is used in the nutrition of larvae and adult queens. It is secreted from the glands in the hypopharynx of nurse bees, and fed to all larvae in the colony, regardless of sex or caste.Graham, J. (ed.) (19 ...

. Characteristic odor. * 10-oxo-7-hydroxy-''trans''-8-decenoic acid. Formed by plants in response to mechanical trauma. * 10-oxo-''trans''-8-decenoic acid. A

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

of the

mushroom A mushroom or toadstool is the fleshy, spore-bearing fruiting body of a fungus, typically produced above ground, on soil, or on its food source. ''Toadstool'' generally denotes one poisonous to humans. The standard for the name "mushroom" is t ...

s ''

Agaricus bisporus ''Agaricus bisporus'' is an edible basidiomycete mushroom native to grasslands in Eurasia and North America. It has two color states while immature – white and brown – both of which have various names, with additional names for the mature ...

'' and ''

Pleurotus pulmonarius ''Pleurotus pulmonarius'', commonly known as the Indian oyster, Italian oyster, phoenix mushroom, or the lung oyster, is a mushroom very similar to ''Pleurotus ostreatus'', the pearl oyster, but with a few noticeable differences. The caps of ''p ...

''. Possibly a fungal

growth hormone Growth hormone (GH) or somatotropin, also known as human growth hormone (hGH or HGH) in its human form, is a peptide hormone that stimulates growth, cell reproduction, and cell regeneration in humans and other animals. It is thus important in h ...

References

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Unspecified isomer. Compound 1159 data sheet. Accessed on 2020-08-21. FAO/WHO JECFA (1998):

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Examples

Free acids and esters

Unspecified isomers and mixtures

Derivatives

See also

References