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Bisabolene

(β): (S)-1-Methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene (γ): (Z)-1-Methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene β: 2044625 γ: 2501191

Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are produced from farnesyl pyrophosphate (FPP) and are present in the essential oils of bisabol, and of a wide variety of other plants including cubeb, lemon, and oregano. Various derivates also function as pheromones in different insects, such as stink bugs and fruit flies. Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear.

Three isomers are known, α-, β-, and γ-bisabolene, which differ by the positions of the double bonds.

Uses

Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds, including hernandulcin, 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 bisabolane.

References

"MetaCyc bisabolene biosynthesis (engineered)".
(1993). "Artifacts and pheromone blends from ''Nezara'' spp. and other stink bug (Heteroptera: Pentatomidae)". Zeitschrift für Naturforschung.
(2001). "Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew)". Archives of Insect Biochemistry and Physiology.
(2015). "Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential". Applied Microbiology and Biotechnology.
"pubchem/alpha-Bisabolene".
"pubchem/beta-Bisabolene".
[http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/terp/bisabo.html Bisabolene derived sesquiterpenoid biosynthesis] {{webarchive. link. (November 2, 2010)
[http://www.flavornet.org/info/495-61-4.html (−)-β-bisabolene], flavornet.org
(13 August 2014). "Alternative Diesel Fuel from Biosynthetic Bisabolene". Intellectual Property Office.

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sesquiterpenes hydrocarbons cyclohexenes

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