(S)-beta-bisabolene
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Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are produced from
farnesyl pyrophosphate Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is an intermediate in the biosynthesis of terpenes and terpenoids such as sterols and carotenoids. It is also used in the synthesis of CoQ (part of the electron transport cha ...
(FPP) and are present in the
essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...
s of
bisabol Opopanax is the commercial name of ''bisabol'' or ''bissabol'', the fragrant oleo- gum-resin of '' Commiphora guidottii''. It has been a major export article from Somalia since ancient times, and is called ''hebbakhade'', ''habaghadi'' or ''habak ...
, and of a wide variety of other plants including cubeb, lemon, and
oregano Oregano (, ; ''Origanum vulgare'') is a species of flowering plant in the mint family Lamiaceae. It was native to the Mediterranean region, but widely naturalised elsewhere in the temperate Northern Hemisphere. Oregano is a woody perennial pla ...
. Various derivates also function as pheromones in different insects, such as
stink bugs Stink bug or stinkbug is a common name for several insects and may refer to: * Any of several bugs in the true bug (hemipteran) family Pentatomidae **''Halyomorpha halys'', or brown marmorated stink bug **''Chinavia hilaris'', or green stink bug * ...
and fruit flies. Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear. Three
isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...
s are known, α-, β-, and γ-bisabolene, which differ by the positions of the double bonds.


Uses

Bisabolenes are intermediates in the
biosynthesis Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. ...
of many other natural chemical compounds, including
hernandulcin Hernandulcin is an intensely sweet chemical compound gained from the chiefly Mexican and South American plant ''Lippia dulcis''. History and origin In the 1570s, Spanish physician Francisco Hernández described a remarkably sweet plant known to ...
, a natural sweetener. β-Bisabolene has a balsamic odor and is approved in Europe as a food additive. Bisabolene has been identified as a biologically producible precursor to a diesel fuel alternative and/or cold weather additive bisabol''ane''.


See also

*
Alpha-bisabolene synthase α-Bisabolene synthase (EC 4.2.3.38, bisabolene synthase) is an enzyme with systematic name (2''E'',6''E'')-farnesyl-diphosphate diphosphate-lyase ((''E'')-α-bisabolene-forming). This enzyme catalyses the following chemical reaction A chemic ...
*
(S)-beta-bisabolene synthase (''S'')-β-bisabolene synthase (EC 4.2.3.55) is an enzyme with systematic name (2''E'',6''E'')-farnesyl-diphosphate diphosphate-lyase ((''S'')-β-bisabolene-forming). This enzyme catalyses the following chemical reaction : (2''E'',6''E'')-farnes ...
*
(E)-gamma-bisabolene synthase (''E'')-γ-bisabolene synthase (EC 4.2.3.59) is an enzyme with systematic name (2''E'',6''E'')-farnesyl-diphosphate diphosphate-lyase ((''E'')-γ-bisabolene-forming). This enzyme catalyses the following chemical reaction : (2''E'',6''E'')-farnes ...
*
(Z)-gamma-bisabolene synthase (''Z'')-γ-bisabolene synthase (EC 4.2.3.40) is an enzyme with systematic name (2''E'',6''E'')-farnesyl-diphosphate diphosphate-lyase ((''Z'')-γ-bisabolene-forming). This enzyme catalyses the following chemical reaction : (2''E'',6''E'')-farnesy ...


References

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External links


Beta-bisabolene
NIST The National Institute of Standards and Technology (NIST) is an agency of the United States Department of Commerce whose mission is to promote American innovation and industrial competitiveness. NIST's activities are organized into physical sci ...
Chemistry WebBook listing Sesquiterpenes Hydrocarbons Cyclohexenes