Studies in detoxication

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Abstract
The optical resolution of dl-menthol was effected through its conjugation with glucuronic acid in the rabbit. Two methods were used: the ammonium salts of the d- and Z-menthylglucuronides, excreted in the urine following the oral adm. of dl-menthol, were fractionally crystallized; l-menthol could be eliminated because the rabbit oxidizes it more easily than (d-menthol. When menthol recovered from a previous adm. of dl-menthol was re-fed, nearly 90% of the l-menthol was oxidized biologically, and the excreted glucuronide was mainly d-menthylglucuronide which was easily purified. d-Menthol, from hydrolysis of d-menthylglucuronide, was obtained in about 10% yield, calculated on the dl-menthol fed. l-Menthol was not readily obtainable in optically pure form by these methods. Following a dose of 3 g. per rabbit the excretion of conjugated menthol is complete in about 30 hr., the material excreted throughout this period having a constant ratio of d- to Z-menthol. The following derivatives of d-menthol are described for the first time: d-menthyl-glucuronide and its ammonium salt, d-menthylphenyl-urethane and d-menthyl 3:5-denitrobenzoate.