Identification and synthesis of the isomeric tetrahydroxytetrahydronaphthalene metabolites excreted in rat urine.
The structures of three isomeric 1,2,3,4-tetrahydroxytetrahydronaphthalene metabolites of naphthalene have been confirmed by synthesis. Six isometric 1,2,3,4-tetrahydroxy-1,2,3,4-tetrahydronaphthalene structures occurring in for dl-pairs and two mesoforms have been synthesized. Five were synthesized by the action of osmium tetroxide on the cis- and trans-1,2-dihydrodiols and cis- and trans-1,4-dihydrodiols. The sixth isomeric tetrahydrotetrol was synthesized by hydrolysis of trans-1,2-dihydroxy-syn-3,4-epoxy-1,2,3,4-tetrahydronaphthalene (the syn-dihydrodiolepoxide of naphthalene). By comparing the gas-chromatographic and mass-spectrometric properties of the synthetic and urinary tetrahydrotetrols, two of the urinary metabolites were identified as 1 beta, 2 alpha, 3 alpha, 4 beta- and structure of the third tetrahydrotetrol metabolite, 1 beta, 2 alpha, 3 beta, 4 alpha-tetrahydroxy-1,2,3,4-tetrahydronaphthalene, identified in earlier studies, was confirmed.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D007536:Isomerism; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000378:metabolism*; D009993:Osmium Tetroxide; D051381:Rats; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000652:urine
D009281:Naphthalenes; D013764:Tetrahydronaphthalenes; D009993:Osmium Tetroxide