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J Chem Ecol

Title:		"Stereoisomeric analysis of 6,10,14-trimethylpentadecan-2-ol and the corresponding ketone in wing extracts from African Bicyclus butterfly species"
Author(s):		Hedenstrom E; Wallin EA; Andersson J; Bang J; Wang HL; Lofstedt C; Brattstrom O; Baquet P;
Address:		"Eco-Chemistry, Department of Chemical Engineering, Mid Sweden University, 851 70, Sundsvall, Sweden, erik.hedenstrom@miun.se"
Journal Title:		J Chem Ecol
Year:		2015
Volume:		20141220
Issue:		1
Page Number:		44 - 51
DOI:		10.1007/s10886-014-0539-5
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
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"
Keywords:		"Alcohols/chemical synthesis/*chemistry Animals Butterflies/*chemistry Chemistry Techniques, Synthetic Female Gas Chromatography-Mass Spectrometry Male Molecular Structure Sex Attractants/chemistry Solid Phase Extraction Stereoisomerism Terpenes/chemical s;"
Notes:		"MedlineHedenstrom, E Wallin, E A Andersson, J Bang, J Wang, H-L Lofstedt, C Brattstrom, O Baquet, P eng Research Support, Non-U.S. Gov't 2014/12/21 J Chem Ecol. 2015 Jan; 41(1):44-51. doi: 10.1007/s10886-014-0539-5. Epub 2014 Dec 20"