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Metabolism of isosafrole and dihydrosafrole in the rat
Author(s) -
Klungsøyr Jarie,
Scheline Ronald R.
Publication year - 1982
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200090803
Subject(s) - methylenedioxy , metabolite , chemistry , hydroxylation , metabolism , epoxide , chromatography , urine , gas chromatography , excretion , biochemistry , enzyme , organic chemistry , alkyl , halogen , catalysis
The urinary metabolites of isosafrole(1,2‐methylenedioxy‐4‐propenylbenzene) and dihydrosafrole (1,2‐methylenedioxy‐4‐propylbenzene) in the rat were identified using gas chromatographic mass spectrometric methods. Additionally, the amounts of the individual metabolites excreted were determined gas chromatographically. Metabolite excretion was 89% (isosafrole) and 97% (dihydrosafrole) of the dose in 72 h. Although isosafrole was metabolized by allylic hydroxylation and via the epoxide‐diol pathway, demethylenation leading mainly to 1,2‐dihydroxy‐4‐propenylbenzene was by far the most prominent reaction. This was similarly true with dihydrosafrole which was metabolized mainly to 1,2‐dihydroxy‐4‐(1‐propyl) benzene. The total amount of demethylenated metabolites formed were 92% (isosafrole) and 95% (dihydrosafrole) of the identified material.