Bisabolene

In today's world, Bisabolene has become a topic of great importance and interest to a wide audience. With the advancement of technology and constant changes in society, Bisabolene has acquired unprecedented relevance. From its impact on people's daily lives to its influence on the global economy, Bisabolene has proven to be a topic of debate and reflection for experts and citizens alike. In this article, we will explore different aspects and perspectives related to Bisabolene, with the aim of offering a comprehensive and enriching vision on this topic that is so relevant today.
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(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 , 100 kPa).

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

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.
  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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