Bombykol

Bombykol
Names
	Preferred IUPAC name (10E,12Z)-Hexadeca-10,12-dien-1-ol
Identifiers
CAS Number	765-17-3 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:41200 ;
ChemSpider	392860 ;
PubChem CID	445128;
UNII	LZT8R8TVZ7 ;
CompTox Dashboard (EPA)	DTXSID00894769 ;
	InChI 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+ Key: CIVIWCVVOFNUST-SCFJQAPRSA-N ; 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;
	SMILES CCC/C=C\C=C\CCCCCCCCCO; OCCCCCCCCC\C=C\C=C/CCC;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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]

^ Kuwahara, Yasumasa (1984). "Flight Time of Bombyx mandarina Males to a Pheromone Trap Baited with Bombykol". Applied Entomology and Zoology. 19 (3): 400–401. Bibcode:1984AppEZ..19..400K. doi:10.1303/aez.19.400.
^ Kuwahara, Yasumasa; Mori, Naoki; Yamada, Shigeki; Nemoto, Tadashi (1984). "Evaluation of Bombykol as the Sex Pheromone of Bombyx mandarina(Lepidoptera : Bombycidae)". Applied Entomology and Zoology. 19 (2): 265–267. Bibcode:1984AppEZ..19..265K. doi:10.1303/aez.19.265.
^ Butenandt, A.; Beckamnn, R.; Hecker, E. (1961). "Über den Sexuallockstoff des Seidenspinners .1. Der biologische Test und die Isolierung des reinen Sexuallockstoffes Bombykol". Hoppe-Seyler's Zeitschrift für Physiologische Chemie. 324: 71–83. doi:10.1515/bchm2.1961.324.1.71. PMID 13689417.
^ "Molecule of the Week". American Chemical Society. 2004. Archived from the original on August 7, 2004. Retrieved March 2, 2013.
^ Leal, Walter S. (2005). "Pheromone Reception". In Schulz, Stefan (ed.). The Chemistry of Pheromones and Other Semiochemicals II. Topics in Current Chemistry. Vol. 240. Springer. pp. 1–36. doi:10.1007/b98314. ISBN 9783540213086. Retrieved March 2, 2013.

[1] Kuwahara, Yasumasa (1984). "Flight Time of Bombyx mandarina Males to a Pheromone Trap Baited with Bombykol". Applied Entomology and Zoology. 19 (3): 400–401. Bibcode:1984AppEZ..19..400K. doi:10.1303/aez.19.400.

[2] Kuwahara, Yasumasa; Mori, Naoki; Yamada, Shigeki; Nemoto, Tadashi (1984). "Evaluation of Bombykol as the Sex Pheromone of Bombyx mandarina(Lepidoptera : Bombycidae)". Applied Entomology and Zoology. 19 (2): 265–267. Bibcode:1984AppEZ..19..265K. doi:10.1303/aez.19.265.

[3] Butenandt, A.; Beckamnn, R.; Hecker, E. (1961). "Über den Sexuallockstoff des Seidenspinners .1. Der biologische Test und die Isolierung des reinen Sexuallockstoffes Bombykol". Hoppe-Seyler's Zeitschrift für Physiologische Chemie. 324: 71–83. doi:10.1515/bchm2.1961.324.1.71. PMID 13689417.

[4] "Molecule of the Week". American Chemical Society. 2004. Archived from the original on August 7, 2004. Retrieved March 2, 2013.

[5] Leal, Walter S. (2005). "Pheromone Reception". In Schulz, Stefan (ed.). The Chemistry of Pheromones and Other Semiochemicals II. Topics in Current Chemistry. Vol. 240. Springer. pp. 1–36. doi:10.1007/b98314. ISBN 9783540213086. Retrieved March 2, 2013.

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