Bombykol

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Bombykol
Names
Preferred IUPAC name
(10E,12Z)-Hexadeca-10,12-dien-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h4-7,17H,2-3,8-16H2,1H3/b5-4-,7-6+ checkY
    Key: CIVIWCVVOFNUST-SCFJQAPRSA-N checkY
  • InChI=1/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h4-7,17H,2-3,8-16H2,1H3/b5-4-,7-6+
    Key: CIVIWCVVOFNUST-SCFJQAPRBG
  • CCC/C=C\C=C\CCCCCCCCCO
  • OCCCCCCCCC\C=C\C=C/CCC
Properties
C16H30O
Molar mass 238.415 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis of bombykol starting from palmitoyl-CoA

Bombykol is a pheromone released by the female silkworm moth to attract mates. It is also the sex pheromone in the wild silk moth (Bombyx mandarina).[1][2] Discovered by Adolf Butenandt in 1959, it was the first pheromone to be characterized chemically.[3]

Minute quantities of this pheromone can be used per acre of land to confuse male insects about the location of their female partners. It can thus serve as a lure in traps to remove insects effectively without spraying crops with large amounts of pesticides. Butenandt named the substance after the moth's Latin name Bombyx mori.[4]

In vivo it appears that bombykol is the natural ligand for a pheromone binding protein, BmorPBP, which escorts the pheromone to the pheromone receptor.[5]

References

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