Metabolism of polycyclic compounds. 11. The conversion of naphthalene into 2-hydroxy-1-naphthyl sulphate in the rabbit

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Abstract
Four rabbits were each injected intraperitoneally on 4 consecutive days with a solution of naphthalene in arachis oil (5 ml of 20%, w/v). The urines were collected up to the 6th day, pooled, centrifuged, acidified to pH 4 with acetic acid and washed several times with ether. Naphthalene metabolites were absorbed on an activated charcoal column and eluted with methanol. The methanol was evaporated to dryness under reduced pressure and the brown gum was rechromato-graphed on cellulose-powder using n-butanol-cyclohexane-water (13:8:1 by volume). A broad band which had violet fluorescence under UV light formed and the fractions which corresponded to the elution of this band were evaporated to form light brown gums. The combined gums were dissolved in water (5 ml) and 5 N NaOH (5 ml) was added, followed by ethanol (50 ml). The 2-hydroxy-1-naphthyl sulfate (980 mg) was recrystallized from aqueous ethanol. The infrared spectrum was identical with the synthetic Na salt and the 2 salts had identical properties on paper chromatograms developed with n-butanol-saturated with 2N NH3 solution, n-butanol-ethanol-water (17:3:20 by volume) or isobutanol-3N-(NH4)2CO3-3N-NH3 solution (4:3:3 by volume).