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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

Åkesson-Nilsson, Gunilla and Wesén, Clas LU (2004) In Journal of Mass Spectrometry 39(11). p.1313-1320
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-dichlorooctaclecanoic acid. This indicates that dichlorinated fatty acids are degraded by beta-oxidation. It is also possible to locate tentatively the position of chlorine atoms in 5,6-dichlorotetradecanoic acid as its methyl ester or... (More)
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-dichlorooctaclecanoic acid. This indicates that dichlorinated fatty acids are degraded by beta-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 (C) 2004 John Wiley Sons, Ltd. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Mass Spectrometry
volume
39
issue
11
pages
1313 - 1320
publisher
John Wiley & Sons
external identifiers
  • pmid:15532069
  • wos:000225339000008
  • scopus:9144269855
ISSN
1076-5174
DOI
10.1002/jms.724
language
English
LU publication?
yes
id
9a973d6a-cdea-4d68-8012-d79d4ca174ec (old id 152680)
date added to LUP
2007-06-25 17:06:32
date last changed
2017-01-01 07:01:45
@article{9a973d6a-cdea-4d68-8012-d79d4ca174ec,
  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-dichlorooctaclecanoic acid. This indicates that dichlorinated fatty acids are degraded by beta-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 (C) 2004 John Wiley Sons, Ltd.},
  author       = {Åkesson-Nilsson, Gunilla and Wesén, Clas},
  issn         = {1076-5174},
  language     = {eng},
  number       = {11},
  pages        = {1313--1320},
  publisher    = {John Wiley & Sons},
  series       = {Journal of Mass Spectrometry},
  title        = {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},
  url          = {http://dx.doi.org/10.1002/jms.724},
  volume       = {39},
  year         = {2004},
}