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Isolation and Identification of Three Urinary Metabolites of Retinoic Acid in the Rat

✍ Scribed by Ralph Hänni; Felix Bigler; Walter Meister; Gerhard Englert

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
432 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

After the intraperitoneal administration of high doses of ^14^C‐ and ^3^H‐labelled retinoic acid (1) to rats three major urinary metabolites have been isolated in microgram amounts by use of column, thin‐layer and high‐pressure liquid chromatography. Their structures were elucidated by mass spectroscopy and Fourier transform ^1^H‐NMR. spectroscopy as 2 (5‐methyl‐5‐[2‐(2,6,6‐trimethyl‐3‐oxo‐1‐cyclohexen‐1‐yl)vinyl]‐2‐tetrahydrofuranone), 3 (5‐[2‐(6‐hydroxymethyl‐2,6‐dimethyl‐3‐oxo‐1‐cyclohexen‐1‐yl)vinyl]‐5‐methyl‐2‐tetrahydrofuranone) and 4 (6‐(6‐hydroxymethyl‐2,6‐dimethyl‐3‐oxo‐1‐cyclohexen‐1‐yl)‐4‐methyl‐4‐hexenoic acid). In these metabolites the tetraene side chain of 1 is shortened and the cyclohexene ring oxidized. The radioactivity of 2 and 3 accounted for about 10% (0.9% of the dose) each, metabolite 4 for about 6% (0.5% of the dose) of the total urinary radioactivity.

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