Bisabolene

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]

Bisabolenes

α-Bisabolene

β-Bisabolene

γ-Bisabolene
Names
IUPAC names
(α): (E)-1-Methyl-4-(6-methylhepta-2,5-dien-2-yl)cyclohex-1-ene
(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
Identifiers
3D model (JSmol)
α: 2414203
β: 2044625
γ: 2501191
ChEBI
ChemSpider
KEGG
UNII
  • α: InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6-8,15H,5,9-11H2,1-4H3/b14-7-
  • β: InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m1/s1
  • γ: InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14+
  • α: CC1=CCC(/C(C)=C/C/C=C(C)/C)CC1
  • β: CC1=CC[C@@H](C(CC/C=C(C)/C)=C)CC1
  • γ: CC(CC/1)=CCC1=C(C)/CC/C=C(C)/C
Properties
C15H24
Molar mass 204.357 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

References
  1. "MetaCyc bisabolene biosynthesis (engineered)". biocyc.org. Retrieved 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. doi:10.1515/znc-1993-1-214. S2CID 40523228. Archived from the original on 2013-04-08. Retrieved 2013-10-22.
  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. doi:10.1002/arch.1067. PMID 11673844.
  4. Spakowicz, Daniel J.; Strobel, Scott A. (2015). "Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential". Applied Microbiology and Biotechnology. 99 (12): 4943–4951. doi:10.1007/s00253-015-6641-y. PMC 4677055. PMID 25957494.
  5. "pubchem/alpha-Bisabolene".
  6. "pubchem/beta-Bisabolene".
  7. Bisabolene derived sesquiterpenoid biosynthesis Archived November 2, 2010, at the Wayback Machine
  8. (−)-β-bisabolene, flavornet.org
  9. "Alternative Diesel Fuel from Biosynthetic Bisabolene". 13 August 2014.
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