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Contents

   



(Top)
 


1 Uses  





2 See also  





3 References  





4 External links  














Bisabolene






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From Wikipedia, the free encyclopedia
 

(Redirected from Β-bisabolene)

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

CAS Number

  • β: 495-61-4 checkY
  • γ: 495-62-5 checkY
  • 3D model (JSmol)

  • β: Interactive image
  • γ: Interactive image
  • Beilstein Reference

    α: 2414203
    β: 2044625
    γ: 2501191
    ChEBI
  • β: CHEBI:49263
  • γ: CHEBI:49237
  • ChemSpider
  • β: 8279897
  • γ: 2298446
  • KEGG

    PubChem CID

  • β: 10104370
  • γ: 3033866
  • UNII
  • β: S19BRC22QA checkY
  • γ: E6941S3U3Q checkY
    • 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

    Chemical formula

    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

    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 oilsofbisabol, 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[edit]

    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[edit]

    References[edit]

    1. ^ "MetaCyc bisabolene biosynthesis (engineered)". biocyc.org. Retrieved 2018-05-28.
  • ^ 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.
  • ^ 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.
  • ^ 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.
  • ^ "pubchem/alpha-Bisabolene".
  • ^ "pubchem/beta-Bisabolene".
  • ^ Bisabolene derived sesquiterpenoid biosynthesis Archived November 2, 2010, at the Wayback Machine
  • ^ (−)-β-bisabolene, flavornet.org
  • ^ "Alternative Diesel Fuel from Biosynthetic Bisabolene". 13 August 2014.
  • External links[edit]


    Retrieved from "https://en.wikipedia.org/w/index.php?title=Bisabolene&oldid=1179974153"

    Categories: 
    Sesquiterpenes
    Hydrocarbons
    Cyclohexenes
    Hidden categories: 
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    Chemical articles with multiple compound IDs
    Chemicals using indexlabels
    Chemical articles with multiple CAS registry numbers
    Chemical articles with multiple PubChem CIDs
    Chemical articles with multiple ChEBIs
    Articles containing unverified chemical infoboxes
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    Short description is different from Wikidata
     



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