Stereoisomeric analysis of 6,10,14-Trimethylpentadecan-2-ol and the corresponding ketone in wing extracts from African Bicyclus butterfly species
Author
Summary, in English
Gas chromatography (GC) and mass spectrometry (MS) were used to determine the stereoisomeric compositions of 6,10,14-trimethylpentadecan-2-ol and 6,10,14-trimethylpentadecan-2-one in wing extracts from 17 Bicyclus butterfly species from different regions of Africa. All samples were purified using solid phase extraction (SPE). Since some species contained both alcohol and ketone, these were separated and the ketone was reduced to the alcohol before analysis as either (R)-trans-chrysanthemoyl or (S)-2-acetoxypropionyl esters. A novel asymmetric synthesis was developed for a reference mixture of (2R/S,6S,10R)-6,10,14-trimethylpentadecan-2-ol with known composition of the eight stereoisomers. The mixture then was used as the (R)-trans-chrysanthemoyl esters to correlate each of the eight gas chromatographic peaks to a specific stereoisomer of the extracted wing compounds. Seven butterfly species showed (2R,6R,10R)-configuration of the alcohol, four species contained minute amounts of alcohol too small to determine the stereochemistry, nine species showed (6R,10R)-configuration of the ketone, and one species contained minute amounts of ketone too small to determine the stereochemistry. No other stereoisomers of alcohol or ketone could be detected in the extracts, and the quantities of the compounds in the wing extracts varied from 5 to 900 ng per sample for each species.
Department/s
Publishing year
2015
Language
English
Pages
44-51
Publication/Series
Journal of Chemical Ecology
Volume
41
Issue
1
Document type
Journal article
Publisher
Springer
Topic
- Zoology
Keywords
- 14-Trimethylpentadecan-2-one
- 10
- 6
- Asymmetric synthesis
- GC/MS
- Wing
- compounds
- Stereoisomers
Status
Published
Project
- Evolutionary mechanisms of pheromone divergence in Lepidoptera
Research group
- Pheromone Group
ISBN/ISSN/Other
- ISSN: 1573-1561