352 VII. ACIDS, AMIDES, ALDEHYDES AND HYDROCARBONS 



OCeHgOe OCeHgOs 



- aX 



1,2-Dihydroanthracene- 1-Anthryl- 1-Hydroxy- 



1,2-diol monoglucuronide glucuronide anthracene 



The Conversion of l,2-Dihydroanthracene-l,2-diol Monoglucuronide to 1-Anthrylglu- 

 curonide by Treatment with Acid, Followed by Hydrolysis to l-Hydroxyanthracene^'* 



The samples of l,2-dihydroanthracene-l,2-diol obtained from the urine 

 of the rat and the rabbit appear to differ in physical properties. '^^ How- 

 ever, both yield the same naphthalene-2,3-dicarboxylic acid on oxidation 

 with potassium permanganate. The yield of the diol is about 0.5% of 

 the anthracene fed. As might be expected, the properties of the glucuroii- 

 ides of the diol also differ in rabbit and rat urine, respectively. 



b'. Anthrylmercapturic Acid: In common with benzene and naphtha- 

 lene, as well as with many other aromatic compounds, anthracene also 

 gives rise to a mercapturic acid derivative when metabolized in the animal 

 body. Boyland and Levi'^^ proved that the increase in the quantity of 

 organic sulfur excreted in the urine of rats and rabbits receiving anthracene 

 was due in part to the presence of anthrylmercapturic acid, which they 

 likewise isolated. In contradistinction to the glucuronides, the mercap- 

 turic acid derivatives in the urine of rats and of rabbits were identical. 

 The sulfur-containing excretion product was shown to be a (or 1) -anthryl- 

 mercapturic acid; the structure was proved by its conversion to a,a' - 

 dianthryldisulfide by alkaline hydrolysis, followed by oxidation with 

 hydrogen peroxide. This compound was changed, by means of nitric 

 acid, to anthraquinone-sulfonic acid, which was transformed, by reaction 

 with HCl and KCIO3, to a-chloroanthraquinone. The structure of the 

 latter is known. 



/^ — SCH.CH-COOH 



NHCOCH3 



w 



a-Anthrylmercapturic Acid 



c'. Anthraquinone : Boyland and Levi'^^ reported the isolation of 

 small amounts of 9,10-anthraquinone, 



O 



