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Compound - serricornin
 


Bedoukain

 
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7-Hydroxy-4,6-dimethylnonan-3-one
7-Hydroxy-4,6-dimethylnonan-3-one

Formula: C11H22O2 
CAS#: 72598-35-7 
MW: 186.29 

[MS]  [ NMR ]  [Behavioural function]  [Chemdraw





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Reference(s) for synthesis of 7-Hydroxy-4,6-dimethylnonan-3-one



Baker, R., and Devlin, J.A. 1983. Synthesis of 4RS,6S,7S-serricornine and the corresponding pair of racemates. J. Chem. Soc. Chem. Comm. 3:147-148.
 
Chuman, T., Kato, K., and Noguchi, M. 1979. Synthesis of (±)-serricornin 4.6-dimethyl-7-hydroxy-nonan-3-one, a sex pheromone of cigarette beetle (Lasioderma serricorne F.). Agric. Biol. Chem. 43:2005.
 
Chuman, T., Kohno, M., Kato, K., and Noguchi, M. 1979. 4,6-Dimethyl-7-hydroxy-nonan-3-one a sex pheromone of the cigarette beetle (Lasioderma serricorne F.). Tetrahedron Lett. 20:2361-2364.
 
Chuman, T., Kohno, M., Kato, K., Noguchi, M., Nomi, H., and Mori, K. 1981. Stereoselective synthesis of erythro-Serricornin (4R,6R,7S)-, and (4S,6R,7S)-4,6-dimethyl-7-hydroxynonan-3-one, stereoisomers of the sex pheromone of cigarette beetle. Agric. Biol. Chem. 45:2019.
 
Chuman, T., Mochizuki, K., Mori, M., Kohno, M., Kato, K., and Noguchi, M. 1985. Lasioderma chemistry. Sex pheromone of cigarette beetle (Lasioderma serricorne F.). J. Chem. Ecol. 11:417-434.
 
Fujita, K., and Mori, K. 2001. New synthesis of serricornin, the female sex pheromone of the cigarette beetle. Biosci. Biotechn. Biochem. 65:1429-1433.
 
Job, A., Nagelsdiek, R., and Enders, D. 2000. Versatile enantioselective synthesis of four diastereomers of serricornin, a sex pheromone of the cigarette beetle, using the samp/ramp-hydrazone method. Coll. Czech. Chem. Comm. 65:524-538.
 
Katsuki, T., and Yamaguchi, M. 1987. Syntheses of optically active insect pheromones (2R,5S)-2-methyl-5-hexanolide, (3S,11S)-3,11-dimethyl-2-nonacosanone and serricornin. Tetrahedron Lett. 28:651-654.
 
Mori, K., and Nomi, H. 1981. Determination of the absolute configuration at C-6 and C-7 of Serricornin (4,6dimethyl-7-hydroxy-3-nonanone), the sex pheromone of the cigarette beetle. Tetrahedron Lett. 22:1127-1130.
 
Mori, K., and Watanabe, H. 1985. A new synthesis of serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone], the sex pheromone of the cigarette beetle. Tetrahedron. 41:3423-3428.
 
Mori, K., Nomi, H., Chuman, T., Kohno, M., Kato, K., and Noguchi, M. 1982. Synthesis and absolute stereochemistry of serricornin [(4S,6S,7S)-4,6-dimethyl-7-hydroxy-3-nonanone]. The sex pheromone of the cigarette beetle. Tetrahedron. 38:3705-3711.
 
Mori, M., Chuman, T., Kato, K., and Mori, K. 1982. A stereoselective synthesis of “natural” (4S,6S,7S)-serricornin, the sex pheromone of cigarette beetle, from levoglucosenone. Tetrahedron Lett. 23:4593-4596.
 
Mori, M., Chuman, T., Kohno, M., Kato, K., Noguchi, M., Nomi, H., and Mori, K. 1982. Absolute stereochemistry of serricornin, the sex pheromone of cigarette beetle, as determined by the synthesis of its (4S,6R,7R)-isomer. Tetrahedron Lett. 23:667-670.
 
Ono, M., Onishi, I., Chuman, T., Kohno, M., and Kato, K. 1980. A novel synthesis of (±)-serriconin 4,6-dimethyl-7-hydroxy-nonan-3-one. The sex pheromone of cigarette beetle (Lasioderma serricorne F.). Agric. Biol. Chem. 44:2259-2260.
 
Takeda, Y., Kobayashi, Y., and Sato, F. 1985. Stereoselective synthesis of natural (4S,6S,7S)-serricornin starting with (3S,4S)-4-hydroxy-3-methyl-hexene. Chem. Lett. 471.
 
Zlokazov, M.V., and Veselovsky, V.V. 2002. New synthesis of serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne). Russ. Chem. Bl. 51:1600-1603.
 

 
Citation: El-Sayed AM 2014. The Pherobase: Database of Insect Pheromones and Semiochemicals. <http://www.pherobase.com>.
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