356 



VII. ACIDS, AMIDES, ALDEHYDES AND HYDROCARBONS 



respectively. Chalmers and Crowfoot-^* isolated a small amount of 

 "BPX" as a crystalline compound, and proved it to be identical with 

 "BPF." It was shown to be a phenolic compound, but was neither 4- 

 hydroxy-3,4-benzpyrene nor 6-hydroxy-3,4-benzpyrene. However, it was 

 later identified as 8-hydroxy-3,4-benzpyrene, by Berenblum and co- 

 workers, ^s^. 284 ^ quinone, identified as 3,4-benzpyrene-5,8-quinone,2^* 

 has likewise been isolated from the feces of mice and rats which had re- 

 ceived 3,4-benzpyrene intraperitoneally.^^^ 



OH 



3,4-Benzpyrene-5,8- 

 qiiinone 



The Metabolism of 3,4-Benzpyrene in Rats to 8-Hydroxy-3,4-Benzpyrene and to 3,4- 



Benzpyrene-5,8-Quinone 



Weigert and Mottram-^^ believe that there are several intermediates in 

 the conversion of 3,4-benzpyrene to 8-hydroxy -3,4-benzpyrene. These 

 workers considered "BPX" and "BPF" to be different, and they have 

 suggested two new intermediates (BPX) and (BPF). The relationship 

 is given in Figure 6. 



(1) In vivo, local production in skin, kidney, lung, and liver (hence 

 in bile). 



(2) In vivo, in the large intestine and occasionally in the lung of rabbits 

 and mice or in vitro by post-mortem autolysis. 



"8 J. G. Chalmers and D. Crowfoot, Biochem. J., 35, 1270-1275 (1941). 

 "6 F. Weigert and J. C. Mottram, Biochem. J., 37, 497-501 (1943). 



