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  • Title: Characterization of new bacterial transformation products of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl) ethane (DDT) by gas chromatography/mass spectrometry.
    Author: Massé R, Lalanne D, Messier F, Sylvestre M.
    Journal: Biomed Environ Mass Spectrom; 1989 Sep; 18(9):741-52. PubMed ID: 2790260.
    Abstract:
    The microbial transformation of DDT, DDD and DDE was studied in Gram-negative strain B-206 and a number of phenolic metabolites were identified as the trimethylsilyl derivatives in the bacterial extracts by gas chromatography/mass spectrometry. The major metabolites of DDT were DDD, DDE, DDMU, 1,1,1-trichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethane, 1,1,1-trichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-hydroxyphenyl) ethane, and 1,1,1-trichloro-2,2-bis-(2-hydroxy-4-chlorophenyl) ethane. Conversely, DDD was mainly degraded into DDE, 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethane and 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-hydroxyphenyl) ethane. Finally, DDE was transformed into DDMU, 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethylene, 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'hydroxyphenyl) ethylene and 1-chloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethylene. The phenolic metabolites exhibited [M - TMSCl]+., [M - HCl - TMSCl]+. and/or [M - HCl - TMSCl - Me]+ fragment ions which reflect the presence of an ortho hydroxyl group in these molecules. Other mass spectral features used to determine their structure are presented and a metabolic scheme accounting for their formation is proposed.
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