354 VII. ACIDS, AMIDES, ALDEHYDES AND HYDROCARBONS 



H2C — CH2 HOOC COOH 0=C C=0 



o 



Acenaphthene Naphthalic acid Naphthalic anhydride 



The Conversion of Acenaphthene to NaphthaUc Acid (Naphthalene-l,8-dicarboxylic 

 Acid) in Rats, and Then to NaphthaUc Anhydride (the Latter Compound May Be 

 Formed during the Isolation of the NaphthaUc Acid from the Urine) 



d. Higher Aromatic Hydrocarbons. Because of the carcinogenic ac- 

 tion of a number of the higher aromatic hydrocarbons, considerable in- 

 formation has been amassed in recent years concerning the intermediary 

 metabohsm of these compounds. According to Boyland and Levi,^^*-^^^ 

 Dobriner et aZ.,^^^ Berenblum and Schoental,-*-''^^ and Berenblum et al.,^^* 

 the polycycHc hydrocarbons usually undergo oxidation to yield phenolic 

 derivatives. The positions of oxidation in vivo differ from those kno\vn to 

 be the most active in vitro, which, in the case of anthracenoid substances, 

 are the weso-positions. 



(a) Four-Ringed Hydrocarbons, a'. Chrysene: This is a non -carcino- 

 genic hydrocarbon, which is most reactive in mono-substitutions in posi- 

 tion 2, while other substitutions lead mainly to ^-position derivatives.^^* 

 Cook and SehoentaP^^ were able to identify all six possible monochrysols. 

 According to Berenblum and Schoental,-"'-^'' 3-methyoxychrysenol is 

 formed in the rat from chrysene, and the substitution does not proceed 

 beyond the mono-stage. The 3-position is a to the naphthalene nucleus. 

 Chrysene is not metabolized to products which increase the ethereal sulfate 

 output of rats. 2''^ 



b'. 1,2-Benzanthracene: Berenblum and SchoentaP^^ demonstrated 

 that intraperitoneally injected 1,2-benzanthracene is eliminated in the 

 feces of mice and rats as 4' -hydroxy- 1,2-benzanthracene. Dickens^^* 



281 K. Dobriner, C. P. Rhoads, and G. I. Lavin, Cancer Research, 2, 95-107 (1942). 

 282 1. Berenblum and R. Schoental, Cancer Research, 3, 145-150 (1943). 



283 I. Berenblum and R. Schoental, Cancer Research, S, 686-688 (1943). 



284 I. Berenblum, D. Crowfoot, E. R. Holiday, and R. Schoental, Cancer Research, 3, 

 151-158(1943). 



28^ M. S. Newman and J. A. Cathcart, /. Org. Chem., 6, 618-622 (1940). 



286 J. W. Cook and R. Schoental, /. Chem. Soc, 1945, 288-293. 



287 1. Berenblum and R. Schoental, Biochem. J., U, 604-606 (1949). 



288 F. Dickens, 22nd Rept. Brit. Empire Cancer Campaign, p. 55; cited by L. Young, 

 Oxidation of Polycyclic Hydrocarbons in the Animal Body, in R. T. WilUams, Biological 

 Oxidation of Aromatic Rings, Biochem. Soc. Symposia, No. 5, Cambridge Univ. Press, 

 27-39 (1950), p. 33. 



