Purification, Stereoisomeric Analysis and Quantification of Sex Pheromone Precursors in Female Whole Body Extracts from Pine Sawfly Species

  title={Purification, Stereoisomeric Analysis and Quantification of Sex Pheromone Precursors in Female Whole Body Extracts from Pine Sawfly Species},
  author={Joakim B{\aa}ng and Erik Hedenstr{\"o}m and Kristina Sj{\"o}din},
  journal={Journal of Chemical Ecology},
A GC-MS method to analyze the stereoisomeric composition of chiral secondary alcohols found in whole body extracts of pine sawfly females was developed. The tested alcohols were derivatized with optically pure (S)-2-acetoxypropionyl chloride prior to GC-MS analysis. Baseline separation was obtained for all sixteen stereoisomers of 3,7,9-trimethyltridecan-2-ol and for the four 3-methylpentadecan-2-ol stereoisomers. For 3,7-dimethyltridecan-2-ol, 3,7-dimethyltetradecan-2-ol and 3,7… Expand
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Summary.The basic chemical structure of the sex pheromone of the pine sawfly Microdiprion pallipes (Fallén) has earlier been identified as the propionate ester ofExpand
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The main component of the sex pheromone secretion of femaleDiprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified asExpand
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Comparison of gas chromatograms of the natural female extract with the eight synthetic threo stereoisomers showed that the pheromone is the (2S,3R,7R,9S)-stereoisomer of 3,7,9-trimethyl-2-tridecyl acetate. Expand
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A gas chromatographic method using electron capture detection for determination of the stereochemical composition of chiralolatile compounds, e.g., pheromone precursor, diprionol, in female sawflies, Neodiprion sertifer, is described. Expand
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Summary.The first identification of a sex pheromone of a pine sawfly (Hymenoptera, Diprionidae) dates back almost thirty years. Since then, female-produced pheromones of over twenty diprionid speciesExpand
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The pine sawfly pheromone precursor 3,7-dimethyl-2-pentadecanol (diprionol) was quantified by gas chromatography in different body parts of virgin female Neodiprions sertifer, suggesting that at least the final steps of the pherosynthesis take place in many parts of the body, possibly in the cuticle. Expand
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Several 3-methylalkan-2-ols precursors to sex pheromones of Diprion pini, Gilpinia pallida, Gilpinia frutetorum, Diprion nipponica, Macrodiprion nemoralis and Microdiprion pallipes were synthesisedExpand
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