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Bombykol

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Bombykol
Names
IUPAC name
(10E,12Z)-hexadeca-10,12-dien-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • 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).
checkY verify (what is checkY☒N ?)

Bombykol is a pheromone released by the female silkworm moth to attract mates. Discovered by Adolf Butenandt in 1959, it was the first pheromone to be characterized chemically.[1] 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 effectively remove insects without spraying crops with large amounts of pesticides. Butenandt named the substance after the moth's Latin name Bombyx mori.[2]

In vivo it appears that bombykol is the natural ligand for a pheromone binding protein, BmorPBP, which escorts the pheromone to the pheromone receptor.[3]

References

  1. ^ Butenandt, A.; Beckamnn, R.; Hecker, E. (1961). "Über den Sexuallockstoff des Seidenspinners .1. Der biologische Test und die Isolierung des reinen Sexuallockstoffes Bombykol". Hoppe-Seylers Zeitschrift für Physiologische Chemie. 324: 71. doi:10.1515/bchm2.1961.324.1.71.
  2. ^ "Molecule of the Week". American Chemical Society. 2004. Archived from the original on August 7, 2004. Retrieved March 2, 2013. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  3. ^ Leal, Walter S. (2005). "Pheromone Reception". In Schulz, Stefan (ed.). The Chemistry of Pheromones and Other Semiochemicals II. Springer. ISBN 9783540213086. Retrieved March 2, 2013.