Bisabolene Explained

Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are produced from farnesyl pyrophosphate (FPP)^[1] 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^[2] and fruit flies.^[3] Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear.^[4]

Three isomers are known, α-, β-, and γ-bisabolene,^{[5] [6]} which differ by the positions of the double bonds.

Uses

Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds,^[7] including hernandulcin, a natural sweetener. β-Bisabolene has a balsamic odor^[8] 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. ^[9]

See also

• Alpha-bisabolene synthase
• (S)-beta-bisabolene synthase
• (E)-gamma-bisabolene synthase
• (Z)-gamma-bisabolene synthase

External links

• Beta-bisabolene, NIST Chemistry WebBook listing

Notes and References

1. Web site: MetaCyc bisabolene biosynthesis (engineered). biocyc.org. 2018-05-28.
2. Aldrich, J.R. . Numata, H. . Borges, M. . Bin, F. . Waite, G.K. . Lusby, W.R. . 1993 . Artifacts and pheromone blends from Nezara spp. and other stink bug (Heteroptera: Pentatomidae) . Zeitschrift für Naturforschung . 48C . 1–2 . 73–79 . 10.1515/znc-1993-1-214 . 40523228 . free . 2013-10-22 . 2013-04-08 . https://web.archive.org/web/20130408120428/http://naldc.nal.usda.gov/download/37736/PDF . dead .
3. Lu . F. . Teal . P.E. . 2001 . Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew) . Archives of Insect Biochemistry and Physiology . 48 . 3 . 144–154 . 10.1002/arch.1067. 11673844 .
4. 99. 12. 4943–4951. Spakowicz. Daniel J.. Strobel. Scott A.. Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential. Applied Microbiology and Biotechnology. 2015. 10.1007/s00253-015-6641-y. 25957494. 4677055.
5. Web site: pubchem/alpha-Bisabolene.
6. Web site: pubchem/beta-Bisabolene.
7. http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/terp/bisabo.html Bisabolene derived sesquiterpenoid biosynthesis
8. http://www.flavornet.org/info/495-61-4.html (−)-β-bisabolene
9. Web site: Alternative Diesel Fuel from Biosynthetic Bisabolene. 13 August 2014.