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Determination of the enantiomeric composition of several insect pheromone alcohols
Authors:E L Plummer  T E Stewart  K Byrne  G T Pearce  R M Silverstein
Affiliation:(1) Present address: FMC Corp., 08540 Princeton, New Jersey;(2) Present address: Thompson-Hayward Co., 66106 Kansas City, Kansas;(3) Present address: Monell Chemical Senses Center, 19104 Philadelphia, Pennsylvania;(4) Present address: Eastman Kodak, 14650 Rochester, New York;(5) College of Environmental Science and Forestry, 13210 Syracuse, New York
Abstract:Details are given for the determination of the enantiomeric composition of several insect pheromone alcohols. The two methods used in the determination were: formation of the derivative with (+)-agr-methoxy-agr-trifluoromethylphenylacetyl chloride and the use of chiral lanthanide shift reagents. The five alcohols studied and their enantiomeric compositions are: sulcatol fromGnathotrichus sulcatus 65ratio35 (+)/(–),trans-verbenol fromDendroctonus frontalis 60ratio40 (+)/(–), 4-methyl-3-heptanol fromScolytus multistriatus 100% (–), seudenol fromDendroctonus pseudotsugae 50ratio50 (+)/(–), and ipsdienol fromIps pini (Idaho) 100% (–). Determinations were done on 50–500 mgrg substrate.
Keywords:pheromone  Gnathotrichus sulcatus  Scolytus multistriatus  Dendroctonus frontalis  Dendroctonus pseudotsugae  Ips pini Idaho  enantiomeric composition  seudenol  sulcatol  trans-verbenol  chiral shift reagents  4-methyl-3-heptonal
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