ISOLATION AND IDENTIFICATION OF THE URINARY METABOLITE OF BIPHENYL DIMETHYL DICARBOXYLATE

Dimethyl-4, 4'-dimethoxy-5, 6, 5', 6'-dimethylenedioxybiphenyl-2, 2'-dicarboxylate(Biphenyl dimethyl dicarboxylate, BDD) is originally an intermediate for the synthesis of schizandrin C analogs. It has been shown to be useful for the treatment of chronic hepatitis.After oral administration of BDD to rats, a water soluble metabolite was separated from urine by TLC. After hydrolysis of the metabolite by incubation with glucuronidase, a compound was isolated by TLC and identified by MS, IR and NMR spectra to be dimethyl-4-hydroxy-4'-methoxy-5, 6, 5', 6'-dimethylenedioxybiphenyl-2, 2'-dicarboxylate(4-demethyl-BDD). The water soluble metabolite in urine is apparently a conjugate of 4-demethyl-BDD with glucuronic acid.After oral administration of ³H-BDD to rats, the main part of the radioactivity in liver or kidney appears to be the glucuronide of 4-demethyl-BDD.