IDENTIFICATION OF NEW SULFUR-CONTAINING METABOLITES OF NAPHTHALENE IN MOUSE URINE

  • 1 January 1982
    • journal article
    • research article
    • Vol. 10  (6) , 624-631
Abstract
Seven acidic S-containing metabolites were isolated from mouse urine following naphthalene administration. The metabolites have been identified as (1-hydroxy-1,2-dihydro-2-naphthalenylthio)acetic acid (I), 2-hydroxy-3-(1-hydroxy-1,2-dihydro-2-naphthalenylthio)propanoic acid (II), (1,2,3,-trihydroxy-1,2,3,4-tetrahydro-4-naphthalenylthio)acetic acid (III) and N-acetyl-S-(1-hydroxy-1,2,-dihydro-2-naphthalenyl)-L-cysteine (IV). The dehydration products of I, II and IV namely 1-(naphthalenylthio)acetic acid (V), 2-hydroxy-3-(1-naphthalenylthio)propanoic acid (VI) and N-acetyl-S-(1-naphthalenyl)-L-cysteine (VII), respectively, were present in several urinary extracts. Nine methylthio derivatives were identified in the neutral extract of urine. These metabolites were the following: 1-methylthionaphthalene, trans-1-hydroxy-2-methylthio-1,2-dihydronaphthalene, 2 stereoisomeric 1,2,3-trihydroxy-4-methylthio-1,2,3,4-tetrahydronaphthalenes, 1,3-di(methylthio)-2,4-dihydroxy-1,2,3,4-tetrahydronaphthalene, 1,4-di(methylthio)-2,3-dihydroxy-1,2,3,4-tetrahydronaphthalene, 2 methylthiohydroxy-naphthalenes and a methylthiodihydroxydihydronaphthalene. Following i.p. administration of N-acetyl-S-(1-hydroxy-1,2-dihydro-2-naphthalenyl)-L-cysteine to mice, the acidic metabolites I, II, and unchanged IV were found. The gas-chromatographic and gas chromatographic-mass spectral properties of the methyl ester-trimethylsilyl derivatives of the acidic S metabolites of naphthalene are presented.