US EPA

58073 

Journal Article 

Mutagenicity in vitro and potential carcinogenicity of chlorinated ethylenes as a function of metabolic oxirane formation 

Greim, H; Bonse, G; Radwan, Z; Reichert, D; Henschler, D 

1975 

Yes 

Biochemical Pharmacology
ISSN: 0006-2952
EISSN: 1873-2968 

24 

21 

2013-2017 

English 

1108881 

10.1016/0006-2952(75)90396-2 

WOS:A1975AW39600021 

http://://WOS:A1975AW39600021
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All chlorinated ethylenes undergo biotransformation in mammalian organisms, the main pathway being an oxidation to oxiranes, as the first step. The stability of these oxiranes varies widely and depends on the number of chlorine substitutions and on the relative position of the substituents in the molecule. Symmetrically substituted oxiranes from the tetrachloro- and the isomeric 1,2-dichloroethylenes seem to be rather stable I),2). In the case of vinyl chloride and trichloroethylene the polarity of the unsymmetrical oxiranes exerts lesser stabilit3 and induces intramolecular rearrangement 3)'4). Attempts to prepare the oxirane with the highest polarity from l.l-dichloroethylene (I.I-DCE) remained unsuccessful till now. In the reaction of I.I-DCE with m-chloroperoxybenzoic acid,the corresponding oxirane could not be detected; instead, the chloroacetyl chloride was isolated as the product of oxirane-rearrangement 5) 

DCN-120379; Mutagens; Bioassays; Pharmacology; Bacteria; Biochemical tests; Liver microsomal metabolism; Laboratory testing; Dose response; Liver microsomes