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Structural characterization of 5,6‐dichlorotetradecanoic acid, an isolated metabolite of 9,10‐dichlorooctadecanoic acid, by studying picolinyl esters, pyrrolidides and methyl esters with electron ionization mass spectrometry
Author(s) -
ÅkessonNilsson Gunilla,
Wesén Clas
Publication year - 2004
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.724
Subject(s) - chemistry , electron ionization , derivatization , metabolite , mass spectrometry , chemical ionization , fragmentation (computing) , mass spectrum , chlorine , chromatography , organic chemistry , fatty acid , ionization , stereochemistry , ion , biochemistry , computer science , operating system
A method is presented for identification of positional isomers of dichlorinated fatty acids, based on derivatization to picolinyl esters prior to gas chromatographic/mass spectrometric analysis in the electron ionization mode. The mass spectra of the picolinyl esters showed structure‐specific fragmentation patterns. By using the picolinyl ester, 5,6‐dichlorotetradecanoic acid was identified as a metabolite from a cell‐culture medium obtained by culturing human cell lines in media supplemented with threo ‐9,10‐dichlorooctadecanoic acid. This indicates that dichlorinated fatty acids are degraded by β‐oxidation. It is also possible to locate tentatively the position of chlorine atoms in 5,6‐dichlorotetradecanoic acid as its methyl ester or pyrrolidide. Copyright © 2004 John Wiley & Sons, Ltd.