PT  - JOURNAL ARTICLE
AU  - Stillwell, W G
AU  - Horning, M G
AU  - Griffin, G W
AU  - Tsang, W S
TI  - Identification and synthesis of the isomeric tetrahydroxytetrahydronaphthalene metabolites excreted in rat urine.
DP  - 1982 Jan 01
TA  - Drug Metabolism and Disposition
PG  - 11--14
VI  - 10
IP  - 1
4099  - http://dmd.aspetjournals.org/content/10/1/11.short
4100  - http://dmd.aspetjournals.org/content/10/1/11.full
SO  - Drug Metab Dispos1982 Jan 01; 10
AB  - 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.