1103. Benzo[a]pyrene
Nomenclature
Description and references
Formerly called 1,2-benzpyrene. Occurs in coal tar, q.v. Isoln by fractionation: Cook et al., J. Chem. Soc. 1933, 395; by adsorption and fluorimetric determn: Hieger, Am. J. Cancer 29, 705 (1937); Winterstein et al., Z. Physiol. Chem. 230, 158, 169 (1934); Naturwissenschaften 22, 237 (1934). Synthesis from pyrene and succinic anhydride: Cook, Hewett, J. Chem. Soc. 1933, 398; Fieser, Fieser, J. Am. Chem. Soc. 57, 782 (1935); Winterstein et al., Ber. 68, 1079 (1935); Fieser et al., J. Am. Chem. Soc. 57, 1509 (1935). Absorption spectrum: Mayneord, Roe, Proc. R. Soc. London A152, 299 (1935). Review: Clar, Polycyclic Hydrocarbons Vol. 1 & 2 (Academic Press, New York, 1964). Review of carcinogenicity studies: IARC Monographs 3, 91-136 (1973). Inhibition of the mutagenicity of the ultimate carcinogenic metabolite of benzo[a]pyrene by ellagic acid: A. W. Wood et al., Proc. Natl. Acad. Sci. USA 79, 5513 (1982). Study of the reaction between this metabolite (benzo[a]pyrene-7,8-diol 9,10-epoxide) and ellagic acid: J. M. Sayer et al., J. Am. Chem. Soc. 104, 5562 (1982). Review: D. H. Phillips, Nature 303, 468-472 (1983). Review of toxicology and human exposure: Toxicological Profile for Polycyclic Aromatic Hydrocarbons (PB95-264370, 1995) 487 pp.
