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Stereoisomeric separation of derivatised 2-alkanols using gas chromatography – mass spectrometry: sex pheromone precursors found in pine sawfly species

Bång, Joakim; Hedenström, Erik and Anderbrant, Olle LU (2012) In Analytical Letters 45(9). p.1016-1027
Abstract (Swedish)
Abstract in Undetermined

Stereoisomers of long-chain secondary alcohols are used as sex pheromone precursors among pine sawflies and some species can be severe pine forest pests. To use their pheromone in environmentally friendly pest management, methods are needed that can determine the stereochemistry of the precursor alcohols. Combinations of 11 acid chloride derivatives and 10 GC columns were evaluated for separation of stereoisomers of 3,7-dimethylundecan-2-ol, 3,7-dimethyldodecan-2-ol, 3,7-dimethyltridecan-2-ol, 3,7-dimethyltetradecan-2-ol, and 3,7-dimethylpentadecan-2-ol. Derivatization with (S)-2-acetoxypropionyl chloride in combination with a Chiraldex B-PA column separated all eight stereoisomers of... (More)
Abstract in Undetermined

Stereoisomers of long-chain secondary alcohols are used as sex pheromone precursors among pine sawflies and some species can be severe pine forest pests. To use their pheromone in environmentally friendly pest management, methods are needed that can determine the stereochemistry of the precursor alcohols. Combinations of 11 acid chloride derivatives and 10 GC columns were evaluated for separation of stereoisomers of 3,7-dimethylundecan-2-ol, 3,7-dimethyldodecan-2-ol, 3,7-dimethyltridecan-2-ol, 3,7-dimethyltetradecan-2-ol, and 3,7-dimethylpentadecan-2-ol. Derivatization with (S)-2-acetoxypropionyl chloride in combination with a Chiraldex B-PA column separated all eight stereoisomers of 3,7dimethylundecan-2-ol, 3,7-dimethyldodecan-2-ol, and 3,7-dimethyltridecan-2-ol. A combination of two different derivatization methods was needed to separate all stereoisomers of the longer chained alcohols 3,7-dimethyltetradecan-2-ol and 3,7-dimethylpentadecan-2-ol. A female extract of the pine sawfly Neodiprion lecontei was also analyzed and the stereochemistry of the sex pheromone alcohol precursor was determined to be (2S,3S,7S)-3,7-dimethylpentadecan-2-ol at an amount of about 7 ng/female. This paper presents the first GC-MS separation of all eight stereoisomers of 3,7-dimethylundecan-2-ol, 3,7dimethyldodecan-2-ol, and 3,7-dimethyltridecan-2-ol in a single analytical run and also the first GC-MS determination of the stereochemistry of the sex pheromone precursor found in females of N. lecontei. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
alcohols, Secondary, Pine sawflies, Neodiprion lecontei, Derivatization, GC-MS, Sex pheromone, Stereoisomers
in
Analytical Letters
volume
45
issue
9
pages
1016 - 1027
publisher
Taylor & Francis
external identifiers
  • wos:000305209100007
  • scopus:84862506238
ISSN
0003-2719
DOI
10.1080/00032719.2012.670789
project
Chemical communication in sawflies
language
English
LU publication?
yes
id
93ae41b0-2ccb-4f99-884c-2f303a3fe1f3 (old id 2863091)
date added to LUP
2012-07-19 11:08:36
date last changed
2017-01-01 06:23:16
@article{93ae41b0-2ccb-4f99-884c-2f303a3fe1f3,
  abstract     = {<b>Abstract in Undetermined</b><br/><br>
Stereoisomers of long-chain secondary alcohols are used as sex pheromone precursors among pine sawflies and some species can be severe pine forest pests. To use their pheromone in environmentally friendly pest management, methods are needed that can determine the stereochemistry of the precursor alcohols. Combinations of 11 acid chloride derivatives and 10 GC columns were evaluated for separation of stereoisomers of 3,7-dimethylundecan-2-ol, 3,7-dimethyldodecan-2-ol, 3,7-dimethyltridecan-2-ol, 3,7-dimethyltetradecan-2-ol, and 3,7-dimethylpentadecan-2-ol. Derivatization with (S)-2-acetoxypropionyl chloride in combination with a Chiraldex B-PA column separated all eight stereoisomers of 3,7dimethylundecan-2-ol, 3,7-dimethyldodecan-2-ol, and 3,7-dimethyltridecan-2-ol. A combination of two different derivatization methods was needed to separate all stereoisomers of the longer chained alcohols 3,7-dimethyltetradecan-2-ol and 3,7-dimethylpentadecan-2-ol. A female extract of the pine sawfly Neodiprion lecontei was also analyzed and the stereochemistry of the sex pheromone alcohol precursor was determined to be (2S,3S,7S)-3,7-dimethylpentadecan-2-ol at an amount of about 7 ng/female. This paper presents the first GC-MS separation of all eight stereoisomers of 3,7-dimethylundecan-2-ol, 3,7dimethyldodecan-2-ol, and 3,7-dimethyltridecan-2-ol in a single analytical run and also the first GC-MS determination of the stereochemistry of the sex pheromone precursor found in females of N. lecontei.},
  author       = {Bång, Joakim and Hedenström, Erik and Anderbrant, Olle},
  issn         = {0003-2719},
  keyword      = {alcohols,Secondary,Pine sawflies,Neodiprion lecontei,Derivatization,GC-MS,Sex pheromone,Stereoisomers},
  language     = {eng},
  number       = {9},
  pages        = {1016--1027},
  publisher    = {Taylor & Francis},
  series       = {Analytical Letters},
  title        = {Stereoisomeric separation of derivatised 2-alkanols using gas chromatography – mass spectrometry: sex pheromone precursors found in pine sawfly species},
  url          = {http://dx.doi.org/10.1080/00032719.2012.670789},
  volume       = {45},
  year         = {2012},
}