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5142556 
Technical Report 
Labeled metabolites of polycyclic aromatic hydrocarbons: IV. 7-Hydroxybenzo(a)pyrene-7-13C 
Duncan, WP; Perry, WC; Engel, JF 
1976 
12 
2 
275-280 
HEEP COPYRIGHT: BIOL ABS. To facilitate an evaluation of the usefulness of 13C labeled BP (benzo(a)pyrene) derivatives, the synthesis and 13C NMR spectral data of 7-hydroxybenzo(a)pyrene-7-13C are reported. The synthesis pathway uses beta-1-pyrenylpropionic acid (I) obtained in 56% yield from commercially available 1-pyrenecarboxaldehyde by malonic ester synthesis. Diborane reduction of I gave a 77% yield of the corresponding alcohol which in turn was converted to the bromide (II) in 68% yield. Reaction of II with potassium cyanide-13C in DMSO (dimethylsulfoxide) followed by hydrolysis, cyclization and aromatization afforded 7-hydroxybenzo(a)pyrene-7-13C (VI) in an overall yield of 20%. The natural abundance 13C NMR spectrum of BP, 0.24 M in chloroform-d, was reported. The resonance at delta 128.77 was assigned to C-7. A chemical shift of 154.95 for C-7 of VI using a 0.30 M solution in acetone-d6 was observed.