Hydroxy-5-methylchrysene

The Suzuki cross-coupling reaction is recognized as a novel, abbreviated method for the synthesis of 2-hydroxychrysene, 2-hydroxy-5-methylchrysene, and 8-hydroxy-5-methyl-chrysene from easily accessible reactants (Eq. (8)) [23]. These phenolic compounds constitute precursors for the synthesis of dihydrodiol and bay-region diol epoxide derivatives of chrysene and 5-methylchrysene, which are implicated as the active forms of carcinogenic polynuclear aromatic hydrocarbons. 

Hydroxymethylchrysene, 200, 201 7-Hydroxy-5-methylchrysene, 201 9-Hydroxy-5-methylchrysene, 201 Hydroxymethyl group, 194-197, 199, 201 N-Hydroxy-1-naphthylamine, 157, 169... 

Okuda, H., Miwa, K., Nojima, H., and Watabe, T., Inactivation of the carcinogen S-hydroxy-methylchrysene by glutathione conjugation via a sulphate ester in hepatic cytosol. Biochem. Pharmacol. 35, 4573-4576 (1986). 

Wilds, A. L., Djerassi, C. Dienone-phenol rearrangement applied to chrysene derivatives. The synthesis of 3-hydroxy-1-methylchrysene and related compounds. J. Am. Chem. Soc. 1946, 68, 1715-1719. 

Several correlations were also found for positions of substitution on the aromatic molecules. 0 methyl-substituted isomers, such as 2- and 3-meth-ylphenanthrene, were more abundant than a-substituted isomers, such as 1- and 4-methylphenanthrene. This trend was observed for the methylna-phthalenes, methylphenanthrenes, and methylchrysenes (II). However, the relative abundances of positions of substitution were not consistent for the methyldibenzothiophenes and methylcarbazoles when compared with the methylphenanthrenes different factors are involved in their production. The methyl-substituted PACs are probably highly related to the alkyl linkages in the original coal structure. For the hydroxy- and amino-substituted PACs, hydrogenation in the SRC II process is an important factor. 

Dimethylchrysene, its 1,2-dihydroxy and 1-hydroxy metabolites, and 1-hydroxy-5-(hydroxymethyl)-6-methylchrysene were resolved on a C g column (A = 254 run) using a complex 30/70-> 100/0 methanol/water gradient [165]. Similarly, dibenz[aj]anthracene (DBA) and thrm metabolites (5,6-dihydroxy-, 3,4-dihydroxy- and 1,2,3,4-tetrahydroxy-DBA) were resolved on a C g column (A = 254 nm) using a complex 60-min 50/50 — 100/0 methanol/water gradient [166]. 

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