Reference

Metabolism of piperonal and piperonyl alcohol in the rat with special reference to the scission of the methylenedioxy group

Metabolism of piperonal and piperonyl alcohol in the rat with special reference to the scission of the methylenedioxy group. Klungsoeyr, Jarle; Scheline, Ronald R. (Sch. Med., Univ. Bergen, Bergen, Norway). Acta Pharm. Suec., 21(1), 67-72 (English) 1984. CODEN: APSXAS. ISSN: 0001-6675. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) The metab. of piperonal (I) [120-57-0] and piperonyl alc. (II) [495-76-1] (1 mmol/kg, orally) was studied in rats. Recoveries of urinary metabolites were 94 and 90%, resp. Metabolite excretion occurred mainly within 24 h. The pathways of metab. were similar with both compds. and gave piperonylglycine [27855-25-0] (71-72% of the dose) and piperonylic acid [94-53-1] (17-20%) as the major metabolites. Demethylenation of the methylenedioxy moiety led to the excretion of 3 catechol derivs. which accounted for 0.7% of the dose. This moderate extent of demethylenation is compared with previous findings of extensive demethylenation of several highly lipophilic methylenedioxyphenyl derivs., and no demethylenation of some hydrophilic derivs.

Metabolism of the proximate carcinogen 1'-hydroxysafrole and the isomer 3'-hydroxyisosafrole

Metabolism of the proximate carcinogen 1'-hydroxysafrole and the isomer 3'-hydroxyisosafrole. Peele, James D., Jr.; Oswald, Edward O. (Dep. Lab. Med., Med. Univ. South Carolina, Charleston, S. C., USA). Bull. Environ. Contam. Toxicol., 19(4), 396-402 (English) 1978. CODEN: BECTA6. ISSN: 0007-4861. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) In the neutral ext. of urine from animals injected with 1'-hydroxysafrole (I) [5208-87-7], unmetabolized I, 3'-hydroxyisosafrole (II) [17581-86-1], 3,4-methylenedioxyphenyl vinyl ketone [30418-53-2] and 2 unidentified metabolites (mol. wts. 180 and 226) were present. In the basic urine ext., the dimethylamino [30418-50-9] and piperidyl Mannich base [30418-51-0] metabolites were detected; the only acidic metabolite found was 3,4-methylenedioxyhippuric acid (III) [27855-25-0]. Neutral urine exts. from rats given II contained unmetabolized II, 3,4-methylenedioxyacetophenone [3162-29-6], and traces of I. No metabolites were seen in the basic fraction and the acidic one contained 3,4-methylenedioxyacetophenone and 3'-(3,4-methylenedioxyphenyl)-3'-hydroxypropionic acid [67191-87-1]. In addn., traces of piperonylic acid [94-53-1] and III were found. The acid-catalyzed rearrangement of I was faster and more complete than that of 1'-hydroxyallylbenzene under identical conditions. A mechanism for the allylic rearrangement of I is proposed.