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Sex pheromone of the pine sawfly Macrodiprion nemoralis (Hymenoptera : Diprionidae): Identification of (2S,3R,7R,9S)-3,7,9-trimethyl-2-tridecanol as the precursor for the active pheromone acetate

Wassgren, Ann-Britt; Bergström, Gunnar; Sierpinski, A; Anderbrant, Olle LU ; Högberg, Hans-Erik and Hedenström, Erik (2000) In Naturwissenschaften 87(1). p.24-29
Abstract
The main component of the sex pheromone precursor in females of Macrodiprion nemoralis was identified as a threo-3,7,9-trimethyl-2-tridecanol isomer, approximately 800 pg per female, by gas chromatography-mass spectrometry. Comparison of mass spectrometric ion chromatograms showed that the natural compound in the female extract has the same retention time and mass spectrum as one of the two synthetic three peaks. The acetate of the synthetic 16-isomer mixture caught a large number of males in the field. confirming the structure of the active pheromone. Comparison of gas chromatograms of the natural female extract with the eight synthetic three stereoisomers showed that the pheromone is the (2S,3R,7R,9S)-stereoisomer of... (More)
The main component of the sex pheromone precursor in females of Macrodiprion nemoralis was identified as a threo-3,7,9-trimethyl-2-tridecanol isomer, approximately 800 pg per female, by gas chromatography-mass spectrometry. Comparison of mass spectrometric ion chromatograms showed that the natural compound in the female extract has the same retention time and mass spectrum as one of the two synthetic three peaks. The acetate of the synthetic 16-isomer mixture caught a large number of males in the field. confirming the structure of the active pheromone. Comparison of gas chromatograms of the natural female extract with the eight synthetic three stereoisomers showed that the pheromone is the (2S,3R,7R,9S)-stereoisomer of 3,7,9-trimethyl-2-tridecyl acetate. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Naturwissenschaften
volume
87
issue
1
pages
24 - 29
publisher
Springer
external identifiers
  • scopus:0033957202
ISSN
1432-1904
DOI
10.1007/s001140050003
project
Chemical communication in sawflies
language
English
LU publication?
yes
id
c815bae8-e058-41b8-acf7-c45c63671c7f (old id 146424)
date added to LUP
2007-06-27 14:38:06
date last changed
2017-07-02 03:29:28
@article{c815bae8-e058-41b8-acf7-c45c63671c7f,
  abstract     = {The main component of the sex pheromone precursor in females of Macrodiprion nemoralis was identified as a threo-3,7,9-trimethyl-2-tridecanol isomer, approximately 800 pg per female, by gas chromatography-mass spectrometry. Comparison of mass spectrometric ion chromatograms showed that the natural compound in the female extract has the same retention time and mass spectrum as one of the two synthetic three peaks. The acetate of the synthetic 16-isomer mixture caught a large number of males in the field. confirming the structure of the active pheromone. Comparison of gas chromatograms of the natural female extract with the eight synthetic three stereoisomers showed that the pheromone is the (2S,3R,7R,9S)-stereoisomer of 3,7,9-trimethyl-2-tridecyl acetate.},
  author       = {Wassgren, Ann-Britt and Bergström, Gunnar and Sierpinski, A and Anderbrant, Olle and Högberg, Hans-Erik and Hedenström, Erik},
  issn         = {1432-1904},
  language     = {eng},
  number       = {1},
  pages        = {24--29},
  publisher    = {Springer},
  series       = {Naturwissenschaften},
  title        = {Sex pheromone of the pine sawfly <i>Macrodiprion nemoralis</i> (Hymenoptera : Diprionidae): Identification of (2S,3R,7R,9S)-3,7,9-trimethyl-2-tridecanol as the precursor for the active pheromone acetate},
  url          = {http://dx.doi.org/10.1007/s001140050003},
  volume       = {87},
  year         = {2000},
}