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Stereoisomeric analysis of 6,10,14-Trimethylpentadecan-2-ol and the corresponding ketone in wing extracts from African Bicyclus butterfly species

Hedenström, Erik; Wallin, Erika A.; Andersson, Johan; Bång, J.; Wang, Hong-Lei LU ; Löfstedt, Christer LU ; Brattström, Oskar and Baquet, P. (2015) In Journal of Chemical Ecology 41(1). p.44-51
Abstract
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
14-Trimethylpentadecan-2-one, 10, 6, Asymmetric synthesis, GC/MS, Wing, compounds, Stereoisomers
in
Journal of Chemical Ecology
volume
41
issue
1
pages
44 - 51
publisher
Springer
external identifiers
  • wos:000348424800006
  • scopus:84925537674
ISSN
1573-1561
DOI
10.1007/s10886-014-0539-5
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
9b6570df-d492-4bfa-8268-ff4a3142dcc4 (old id 5204198)
date added to LUP
2015-03-25 16:32:12
date last changed
2017-01-01 06:19:24
@article{9b6570df-d492-4bfa-8268-ff4a3142dcc4,
  abstract     = {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.},
  author       = {Hedenström, Erik and Wallin, Erika A. and Andersson, Johan and Bång, J. and Wang, Hong-Lei and Löfstedt, Christer and Brattström, Oskar and Baquet, P.},
  issn         = {1573-1561},
  keyword      = {14-Trimethylpentadecan-2-one,10,6,Asymmetric synthesis,GC/MS,Wing,compounds,Stereoisomers},
  language     = {eng},
  number       = {1},
  pages        = {44--51},
  publisher    = {Springer},
  series       = {Journal of Chemical Ecology},
  title        = {Stereoisomeric analysis of 6,10,14-Trimethylpentadecan-2-ol and the corresponding ketone in wing extracts from African <i>Bicyclus</i> butterfly species},
  url          = {http://dx.doi.org/10.1007/s10886-014-0539-5},
  volume       = {41},
  year         = {2015},
}