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Stereoisomeric separation of derivatised 2-alkanols using gas chromatography – mass spectrometry: sex pheromone precursors found in pine sawfly species
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- Bång, Joakim (author)
- Mittuniversitetet,Mid Sweden University,Institutionen för tillämpad naturvetenskap och design (-2013)
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- Hedenström, Erik (author)
- Mittuniversitetet,Mid Sweden University,Institutionen för tillämpad naturvetenskap och design (-2013)
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- Anderbrant, Olle (author)
- Lund University,Lunds universitet,Funktionell zoologi,Biologiska institutionen,Naturvetenskapliga fakulteten,Functional zoology,Department of Biology,Faculty of Science,Lund Univ, Dept Biol, Lund, Sweden
- (creator_code:org_t)
- Informa UK Limited, 2012
- 2012
- English.
- In: Analytical Letters. - : Informa UK Limited. - 0003-2719 .- 1532-236X. ; 45:9, s. 1016-1027
- Journal article (peer-reviewed)
Abstract
Subject headings
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- Abstract in UndeterminedStereoisomers 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.
Subject headings
- NATURVETENSKAP -- Biologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences (hsv//eng)
- NATURVETENSKAP -- Biologi -- Zoologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences -- Zoology (hsv//eng)
- NATURVETENSKAP -- Kemi -- Analytisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Analytical Chemistry (hsv//eng)
Keyword
- alcohols
- Secondary
- Pine sawflies
- Neodiprion lecontei
- Derivatization
- GC-MS
- Sex pheromone
- Stereoisomers
- Stereoisomers
Publication and Content Type
- art (subject category)
- ref (subject category)
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