HYDROCARBONS 351 



In the case of decalin, Bernhard"* was able to account for 33% of the 

 CIS- and ^rans-hydrocarbons administered, in the form of decahydronaph- 

 thol. However, httle glucuronide formation took place, and Bernhard"* 

 believed that most of the decalin was completely oxidized in the animal. 



c. Three-Ringed Hydrocarbons, (a) Anthracene. Although anthra- 

 cene is a compound having a coefficient of digestibility of only 31 according 

 to Chang, -"^ the proportion which is absorbed follows metabolic pathways 

 not too remote from those of benzene and naphthalene."* The products 

 excreted in the urine include l,2-dihydroxy-l,2-dihydroanthracene and 

 its glucuronide, a hydroxy-dihydroanthracene, 1-anthrylmercapturic 

 acid, and possibly 9,10-anthraquinone.^^^'^^® Elson et al."""^ reported that 

 no ethereal sulfate was formed as a result of the metabolism of anthracene 

 in the rat. Bo\'land and Le^'i^^^•^^* have been extremely active in investi- 

 gating the metabohsm of anthracene. 



a'. Dihydroxydihydroanthracene : Boyland and Levi^^^ isolated and 

 identified l,2-dihydroxy-l,2-dihydroanthracene (also called 1,2-dihydro- 

 anthracene-l,2-diol) in the urine of rats and rabbits which had received 

 anthracene. Booth and Boyland^*' are of the opinion that this compound 

 has a trans configuration. 



Anthracene 1,2-Dihydroanthracene l-Hydroxyanthracene 



1,2-diol 



The Conversion of Anthracene to 1 ,2-Dih5'droanthracene-l ,2-Diol in the Animal 

 Body, and Its Further Conversion to l-Hydroxyanthracene bj^ Heating with Dilute 



HCl 



l,2-Dihydroanthracene-l,2-diol differs from anthracene by having an 

 additional H2O2. The formation of such a compound is referred to as 

 ' 'perhydroxylation . " 



Boyland and Levi^^* also isolated a monoglucuronide of 1,2-dihydroxy- 

 anthracene-l,2-diol from the urine of rats and rabbits which had been 

 treated with anthracene. The compound was shown to have the glucuronic 

 acid combined ■wath the 1-hydroxyl, since on treatment wdth acid it jdelded 

 1-anthrylglucuronide, which in turn could be changed to 1-hydroxyanthra- 

 cene by hydrolysis. 



"* L. H. Chang, /. Biol. Chem., 151, 93-99 (1943). 



="6 A. A. Levi and E. Boyland, Chemistry & Industry, 56 (15), 446 (1937). 



="' L. A. Elson, F. Goulden, and F. L. Warren, Biochem. J., 39, 301-308 (1945). 



