Bergamotene

Chemical compound From Wikipedia, the free encyclopedia

Bergamotenes are a group of isomeric chemical compounds with the molecular formula C15H24. The bergamotenes are found in a variety of plants, particularly in their essential oils.

Quick facts Names, Identifiers ...
Bergamotenes
α-cis-bergamotene
α-trans-bergamotene
β-cis-bergamotene
β-trans-bergamotene
Names
IUPAC names
(α): 2,6-Dimethyl-6-(4-methylpent-3-enyl)bicyclo[3.1.1]hept-2-ene
(β): 6-Methyl-2-methylidene-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]heptane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • (α-trans): InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m0/s1
    Key: YMBFCQPIMVLNIU-SOUVJXGZSA-N
  • (α-cis): InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15-/m0/s1
    Key: YMBFCQPIMVLNIU-KKUMJFAQSA-N
  • (β-trans): InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6,13-14H,3,5,7-10H2,1-2,4H3/t13-,14-,15-/m0/s1
    Key: DGZBGCMPRYFWFF-KKUMJFAQSA-N
  • (β-cis): InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6,13-14H,3,5,7-10H2,1-2,4H3/t13-,14-,15+/m0/s1
    Key: DGZBGCMPRYFWFF-SOUVJXGZSA-N
  • (α): CC1=CCC2CC1C2(C)CCC=C(C)C
  • (β) (β): CC(=CCCC1(C2CCC(=C)C1C2)C)C
  • (β-cis): CC(=CCC[C@@]1([C@H]2CCC(=C)[C@@H]1C2)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 Â°C [77 Â°F], 100 kPa).
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There are two structural isomers, α-bergamotene and β-bergamotene, which differ only by the location of a double bond. Both of these isomers have stereoisomers, the most common of which are known as the cis and trans-isomers (or endo- and exo-isomers).

α-Bergamotene is found in the oils of carrot, bergamot, lime, citron, cottonseed, and kumquat.[1][2]

Pheromones

The bergamotenes are pheromones for some insects. For example, β-trans-bergamotene is a pheromone for the wasp Melittobia digitata.[3] Plants can defend themselves against attack by herbivorous insects by producing pheromones such as bergamotenes that attract predators of those herbivores.[4][5] In a more complex relationship, the tobacco plant Nicotiana attenuata emits α-trans-bergamotene from its flowers at night to attract the tobacco hawk moth (Manduca sexta) as a pollinator; however, during the day the leaves produce α-trans-bergamotene to lure predatory insects to feed on any larvae and eggs that the pollinator may have produced.[6][7]

Biosynthesis

All the bergamotenes are biosynthesized from farnesyl pyrophosphate[8] via a variety of enzymes including exo-alpha-bergamotene synthase, (+)-endo-beta-bergamotene synthase, (-)-endo-alpha-bergamotene synthase, and others. Bergamotenes, in turn, are intermediates in the biosynthesis of more complex chemical compounds. For example, β-trans-bergamotene is a precursor in the biosynthesis of fumagillin, ovalicin, and related antibiotics.[8][9]

References

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