US EPA

2196683 

Journal Article 

Structure of a major metabolite of 2,2',4,5,5'-pentachlorobiphenyl in mice 

Sundstrom, G; Wachtmeister, CA 

1975 

Yes 

Chemosphere
ISSN: 0045-6535
EISSN: 1879-1298 

4 

1 

7-11 

English 

10.1016/0045-6535(75)90040-5 

The characterization of the phenolic metabolite 2,2',4,5,5'-pentachlorobiphenyl (37680732), through the use of simple degradation and derivatization reactions and through comparisons with synthetic material using combined gas chromatography/mass spectrometry (GC-MS) is presented. The proposed technique should be adaptable to the structural elucidation of hydroxychlorobiphenyls in general. Previous investigations on the metabolism of structurally defined chlorobiphenyls have shown that in rats and mice hydroxylation takes place in the 3 position when the 4 position is substituted with chlorine-(5,6 or 8). It is surprising that the present compound containing the same structural unit, i.e. the 2,5-dichlorophenyl ring, only gives rise to the 3-hydroxy compound. The possibility that the formation in the rat of the 4-hydroxy-isomer was overlooked must be considered as minute since the synthesized isomeric phenols all showed practically identical behavior in partition experiments between organic solvents and 2 molar solution of sodium-hydroxide.