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Exocarpic acid is an unsaturated, conjugated
Exocarpic acid is an unsaturated, conjugated fatty acid
In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...
with 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 ...
and two triple bond
A triple bond in chemistry is a chemical bond between two atoms involving six Electron pair bond, bonding electrons instead of the usual two in a covalent bond, covalent single bond. Triple bonds are stronger than the equivalent covalent bond, sin ...
s. It is isomeric to isanic acid and belongs to the class of alkyne and alkenoic acids, as well as the diynes and enyne
An enyne is an organic compound containing a double bond (alkene) and a triple bond (alkyne). It is called a conjugated enyne when the double and triple bonds are conjugated.
The term is a contraction of the terms alkene and alkyne.
The si ...
s. The acid's delta notation is 18:3-delta-9a,11a,13t. Its structural formula is CH 3(CH2)3-CH=CH-C≡CC≡C-(CH2)7-COOH.
The acid was initially isolated in 1959, by H. H. Hatt and co-workers, from the roots of the Australian tree ''Exocarpos cupressiformis
''Exocarpos cupressiformis'' is a tree belonging to the plant family Santalaceae. Its common names include native cherry, cherry ballart, and cypress cherry. It is a species endemic to Australia. Occasionally, the genus is spelled as "Exocarpus" ...
''; from this genus they derived the common name of exocarpic acid.
Natural occurrence
Exocarpic acid is found in various plant species of the order ''Santalales
The Santalales are an order (biology), order of flowering plants in the dicotyledons. Well-known members of the Santalales include Santalum, sandalwoods and the many species of mistletoes. The order has a cosmopolitan distribution, but is heavily ...
''.
In the family ''Olacaceae
Olacaceae is a family of flowering plants in the order Santalales. They are woody plants, native throughout the tropical regions of the world. , the circumscription of the family varies; some sources maintain a broad family, others split it int ...
'', it occurs, among others, in the seed oils of ''Curupira tefeensis'' and ''Olax dissitiflora''. In the family ''Santalaceae
The Santalaceae, sandalwoods, are a widely distributed family of flowering plants (including small trees, shrubs, perennial plants, perennial herbs, and epiphyte, epiphytic climbersHewson & George t al.'Santalaceae'' taxonomy, 1984, pp. 191-1 ...
'', it occurs in several species of the genus ''Thesium
''Thesium'' is a genus of flowering plants in the family Santalaceae. It is particularly well represented in South Africa.
The following species are recognised by ''The Plant List
The Plant List was a list of botanical names of species of p ...
'', such as mountain flax and ''Thesium chinense'', as well as in several species of the genus ''Buckleya
''Buckleya'' is an Asian and American genus of hemiparasitic shrubs in the sandalwood family.
It is named for Samuel Botsford Buckley. ''Buckleya'' is also known as piratebush. Plants of this species are dioecious
Dioecy ( ; ; adj. dioecious, ...
'', such as ''Buckleya lanceolata'' and '' Exocarpos sparteus''. It also occurs in small amounts in the isano oil from ''Ongokea gore
''Ongokea'' is a genus of flowering plants, with one species ''Ongokea gore'' (Boleko). In the APG IV system, the genus is placed in the family Olacaceae. Other sources place it in the segregate family Aptandraceae.
Its native range is Western ...
''.
The parasitic plant ''Sarcophyte sanguinea'' from the family ''Balanophoraceae
The Balanophoraceae are a subtropical to tropical family of obligate parasitic flowering plants, notable for their unusual development and formerly obscure affinities. In the broadest circumscription, the family consists of 16 genera. Alterna ...
'' contains free (i.e., not present in the form of glycerides) exocarpic acid.
Characteristics
Exocarpic acid exerts antibacterial activity against ''Mycobacterium tuberculosis
''Mycobacterium tuberculosis'' (M. tb), also known as Koch's bacillus, is a species of pathogenic bacteria in the family Mycobacteriaceae and the causative agent of tuberculosis.
First discovered in 1882 by Robert Koch, ''M. tuberculosis'' ha ...
'' by inhibiting the biosynthesis of mycolic acid
Mycolic acids are long fatty acids found in the cell walls of Mycobacteriales taxon, a group of bacteria that includes ''Mycobacterium tuberculosis'', the causative agent of the disease tuberculosis. They form the major component of the cell wall ...
s. The acid also exerts antibacterial activity against several bacteria that cause oral infections.
References