SYNTHESIS AND BIOLOGICAL ACTIVITY OF BOTH (E)- AND (Z)-ISOMERS OF OPTICALLY PURE (S)-14-METHYL-8-HEXADECENAL (TROGODERMAL), THE ANTIPODES OF THE PHEROMONE OF THE KHAPRA BEETLE
Both (E)- and (Z)-isomers of (S)-14-methyl-8-hexadecenal (trogodermal) were synthesized from 100percent optically pure (R)-(+)-citronellic acid.These antipodes of the khapra beetle pheromone were 1/500 to 1/1000 times as active as the natural (R)-pheromone.Determination of the optical purities of citronellic acid and related compounds was achieved by hplc method.Warning was made not to forget the measurement of density in expressing the optical rotation of a neat liquid as D (neat).
Mori, K.,Kuwahara, S.,Levinson, H. Z.,Levinson, A. R.
Synthesis of the four stereoisomers of 3,12-dimethylheptacosane, (Z)-9-pentacosene and (Z)-9-heptacosene, the cuticular hydrocarbons of the ant, Diacamma sp..
All of the four stereoisomers of 3,12-dimethylheptacosane were synthesized from the enantiomers of citronellal. (Z)-9-Pentacosene and (Z)-9-heptacosene were also synthesized. These hydrocarbons are the characteristic components of the cuticular hydrocarbo
Masuda, Yui,Mori, Kenji
p. 1032 - 1038
(2007/10/03)
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