Premium
Mass spectra of acetylenic fatty acid methyl esters and derivatives
Author(s) -
Kleiman R.,
Bohan M. B.,
Gunstone F. D.,
Barve J. A.
Publication year - 1976
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02532872
Subject(s) - degree of unsaturation , chemistry , double bond , triple bond , mass spectrum , silylation , mass spectrometry , medicinal chemistry , stereochemistry , organic chemistry , ion , catalysis , chromatography
A series of isomeric methyl octadecynoates was analyzed by mass spectrometry; each isomer gave a unique spectrum. The characteristic ions were those resulting from a McLafferty rearrangement of the allenic sites or of the already‐rearranged allenic sites. The acetylenic esters were also subjected to oxymercuration whereupon a carbonyl group was formed at either of the original actylenic carbon atoms providing two oxostearates. Further reaction with NaBH 4 formed hydroxy esters which, after silylation, gave diagnostic mass spectra indicative of the triple bond location. Applied to esters with both double and triple bonds, this procedure permitted differentiation between the two types of unsaturation. Methoxyl groups marked the original double bond locations and hydroxyls did so for triple bonds.