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Electron ionization mass spectral fragmentation of C19 isoprenoid aldehydes and carboxylic acid methyl and trimethylsilyl esters

Authors :
Corinne Aubert
J.-F. Rontani
Source :
Rapid Communications in Mass Spectrometry. 17:949-956
Publication Year :
2003
Publisher :
Wiley, 2003.

Abstract

The electron ionization (EI) mass spectra of saturated and α,β-unsaturated C19 isoprenoid aldehydes and carboxylic acid methyl and trimethylsilyl esters are reported. Different pathways are proposed in order to explain the main fragmentations observed. The conjugated double bond migrates more or less readily before γ-hydrogen rearrangement according to the structure of the considered compound. Configurations of the double bond of α,β-unsaturated C19 isoprenoid aldehydes and fatty acid methyl and trimethylsilyl esters can be easily determined thanks to the peaks at m/z 97, 127 and 185, respectively, which are much more abundant in the mass spectra of the Z isomers owing to the formation of a cyclic ion. In the case of trimethylsilyl esters, subsequent fragmentation of the cyclic ion at m/z 185 affords two other diagnostic ions at m/z 95 and 169. Copyright © 2003 John Wiley & Sons, Ltd.

Details

ISSN :
10970231 and 09514198
Volume :
17
Database :
OpenAIRE
Journal :
Rapid Communications in Mass Spectrometry
Accession number :
edsair.doi.dedup.....d8420ff5df1ec9f2d4237125fc42c175
Full Text :
https://doi.org/10.1002/rcm.1004