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Identification of long‐chain fatty acids and alcohols from human cerumen by the use of picolinyl and nicotinate esters
Author(s) -
Harvey D. J.
Publication year - 1989
Publication title -
biomedical and environmental mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0887-6134
DOI - 10.1002/bms.1200180912
Subject(s) - chemistry , degree of unsaturation , gas chromatography , trimethylsilyl , double bond , organic chemistry , osmium tetroxide , hydrolysis , squalene , chromatography , carbon chain , branching (polymer chemistry) , alkaline hydrolysis , stereochemistry , electron microscope , physics , optics
Human cerumen was hydrolysed with base and the constituents were examined as trimethylsilyl (TMS), methyl ester/TMS, picolinyl/TMS and nicotinate/TMS derivatives by gas chromatography and gas chromatography/mass spectrometry. A sample was also reacted with osmium tetroxide for double bond location. The major constituents were cholesterol, squalene and several series of long‐chain fatty acids and alcohols. These latter compounds had chain lengths of 12–26 carbon atoms and were predominantly either straight‐chain saturated or straight‐chain unsaturated compounds. Saturated branched‐chain acids with methyl groups predominantly on even‐numbered carbon atoms were present but were less abundant. Unsaturated, branched‐chain acids were also present. The major unsaturated acids contained unsaturation at the delta‐6‐position or were derived from these acids by chain elongation. The compounds were similar to those found in vernix caseosa. The mass spectra of picolinyl esters were, for the first time, shown to be capable of determining both the position of unsaturation and methyl branching in the same molecule.