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Bisabolene

From Wikipedia, the free encyclopedia
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 mass204.357 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Bisabolenes are a group of closely related natural chemical compounds which are classified assesquiterpenes. Bisabolenes are produced fromfarnesyl pyrophosphate (FPP)[1] and are present in theessential oils ofbisabol, and of a wide variety of other plants includingcubeb,lemon, andoregano. Various derivates also function aspheromones in differentinsects, such asstink bugs[2] andfruit flies.[3] Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear.[4]

Threeisomers are known, α-, β-, and γ-bisabolene,[5][6] which differ by the positions of thedouble bonds.

Uses

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Bisabolenes are intermediates in thebiosynthesis of many other natural chemical compounds,[7] includinghernandulcin, 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 adiesel fuel alternative and/or cold weather additive bisabolane.[9]

See also

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References

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  1. ^"MetaCyc bisabolene biosynthesis (engineered)".biocyc.org. Retrieved2018-05-28.
  2. ^Aldrich, J.R.; Numata, H.; Borges, M.; Bin, F.; Waite, G.K.; Lusby, W.R. (1993)."Artifacts and pheromone blends fromNezara spp. and other stink bug (Heteroptera: Pentatomidae)".Zeitschrift für Naturforschung.48C (1–2):73–79.doi:10.1515/znc-1993-1-214.S2CID 40523228.
  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 biosynthesisArchived November 2, 2010, at theWayback Machine
  8. ^(−)-β-bisabolene, flavornet.org
  9. ^Erik (13 August 2014)."Alternative Diesel Fuel from Biosynthetic Bisabolene".Intellectual Property Office.

External links

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