Studies in detoxication. 20. The metabolism of benzene. II. The isolation of phenol, catechol, quinol and hydroxyquinol from the ethereal sulphate fraction of the urine of rabbits receiving benzene orally

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Abstract
The color reactions of phenols with FeCl3, 2,6-dichloroquinone-chloroimide and concentrated H2SO4 and the melting points of benzoates and p-toluene sulfonates of phenols are tabulated. Phenol, catechol, quinol and hydroxyquinol were isolated from the ethereal sulfate fraction of the urine of rabbits receiving benzene orally on 2 consecutive days. The phenols isolated amounted to 3.5% of the dose of benzene. Phenol is excreted first and then catechol and quinol; hydroxyquinol is only found in appreciable amounts on the 3d and 4th days after the initial dose of benzene. The results suggest the following sequence in the oxidation of benzene: benzene[forward arrow]phenol [forward arrow] catechol (and quinol) [forward arrow]hydroxyquinol. The phenols excreted are almost entirely conjugated. Only traces of phenol, and none of the polyhydric phenols, are excreted in the free state.