Oxychlordane, Animal Metabolite of Chlordane: Isolation and Synthesis

Abstract

Oxychlordane (C(10)H(4)Cl(8)O), a minor heretofore unidentified metabolite, was isolated from fat of pigs on diets heavily dosed with pure isomers of the insecticide, chlordane (C(10)H(6)Cl(8)). Chemical and spectroscopic evidence provides bases for proposal of structure of the metabolite as 1-exo-2-endo-4,5,6,7,8,8-octachloro-2,3-exo-epoxy-2,3,3a,4,7,7a-hexahydro-4,7-methanoindene.

Depuration rates of chlordane compounds from rat fat

“…The endo isomer, gCL, produces an optically active form of OXY, but the exo isomer, aCL, is metabolized to a racemic mixture of OXY isomers (13). The endo isomer, gCL, produces an optically active form of OXY, but the exo isomer, aCL, is metabolized to a racemic mixture of OXY isomers (13).…”

Metabolism, tissue distribution, and elimination of cis-[14C]chlordane in the tropical freshwater fish, Cichlasoma species

“…Korte (1964, 1971) showed that trons-chlordane administered to rats and rabbits was rapidly metabolized and eliminated. Identification, characterization, and probable pathway of formation of oxychlordane from chlordanes (Schwemmer et al, 1970; Lawrence et al, 1970;Polen et al, 1971; Street and Blau, 1972) was another important development in the toxicology of chlordanes. Detailed investigation of the in vivo metabolism of chlordanes was carried out by Barnett and Dorough (1974).…”

Metabolic routes of cis- and trans-chlordane in rats

“…In terms of metabolic fates of chlordane in animals, so far, the center of attention has been the formation of oxychlordane, the acknowledged toxic metabolic product both from cis-and trons-chlordane (Schwemmer et al, 1970; Lawrence et al, 1970; Polen et al, 1971; Street and Department of Entomology, University of Wisconsin, Madison, Wisconsin 53706. Blau, 1972; Dorough and Hemken, 1973).…”