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
✍ Scribed by Gunilla Åkesson-Nilsson; Clas Wesén
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- English
- Weight
- 168 KB
- Volume
- 39
- Category
- Article
- ISSN
- 1076-5174
- DOI
- 10.1002/jms.724
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✦ Synopsis
Abstract
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.