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.
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 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.
Akesson-Nilsson
Gunilla
G
Department of Chemistry and Biomedical Sciences, University of Kalmar, SE-391 82 Kalmar, Sweden. gunilla.akesson-nilsson@hik.se
Wesén
Clas
C
D002478:Cells, Cultured; D002713:Chlorine / Q000032:analysis / Q000737:chemistry* / Q000378:metabolism; D004777:Environment; D004952:Esters / Q000032:analysis / Q000737:chemistry*; D005227:Fatty Acids / Q000032:analysis / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D010084:Oxidation-Reduction; D010848:Picolinic Acids / Q000032:analysis / Q000737:chemistry*; D011759:Pyrrolidines / Q000032:analysis / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D004952:Esters; D005227:Fatty Acids; D010848:Picolinic Acids; D011759:Pyrrolidines; D002713:Chlorine