Metabolism of 4-hydroxyanisole: identification of major urinary excretory products.

Abstract

The human metabolism of 4-hydroxyanisole was investigated by the analysis of urine samples from melanoma patients treated with this substance. The samples were hydrolyzed with glucoronidase and/or arylsulphatase, extracted with ethyl acetate, and, after derivatization with pentafluoropropionylanhydride, analyzed by gas chromatography-mass spectrometry. We were able to identify peaks by their retention times and mass spectra corresponding to 4-hydroxyanisole, 3,4-dihydroxyanisole, and two of its o-methyl derivatives, namely, 3-hydroxy-4-methoxy- and 4-hydroxy-3-methoxyanisole. We also detected a peak of hydroquinone, which may have originated (at least partly) from 4-hydroxyanisole. All the above-mentioned compounds were excreted predominantly as sulphates and glucuronides. Only a small proportion of the substances was present in urine in an unconjugated form. Our results demonstrate that 3,4-dihydroxyanisole is the most important metabolite of 4-hydroxyanisole.

• Authors: S Pavel, J L Holden, P A Riley
• Journal: Pigment cell research (Pigment Cell Res) 1989 Sep-Oct Vol. 2 Issue 5 Pg. 421-6 ISSN: 0893-5785 [Print] Denmark
• PMID: 2587513 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Anisoles
• Antineoplastic Agents
• mequinol

Topics

• Anisoles (metabolism, therapeutic use, urine)
• Antineoplastic Agents (urine)
• Gas Chromatography-Mass Spectrometry
• Humans
• Mass Spectrometry
• Melanoma (drug therapy, urine)
• Neoplasm Recurrence, Local
• Skin Neoplasms (drug therapy, urine)