CHOL1C ACID. 401 



rCHOH 

 C24H 40 O 5 , = C 20 H 31 \ (CH 2 OH) 2 . According to MvLius, 1 cholic acid is a 



ICOOH 



monobasic alcohol-acid with one secondary and two primary alcohol 

 groups. CURTIUS 2 has shown by preparing the cholamine, C 23 H S9 O 3 .NH 2 , 

 from the above-mentioned (p. 397) cholic-acid azide, with cholic-acid 

 urethane as an intermediary step, that the carboxyl group. is not imme- 

 diately connected with the CHOH group, but is combined with the chief 

 nucleus without the neighboring secondary alcohol group. On oxida- 

 tion it first yields dehydrocholic acid, C 24 H 34 O 5 (HAMMARSTEN). On 

 further oxidation bilianic acid, C 2 4H 34 O 8 (CLEVE), is obtained, or, more 

 correctly, according to LATSCHINOFF, LASSAR-CO'HN and PREGL, a mix- 

 ture of bilianic and isobilianic acids discovered by LATSCHINOFF. On 

 oxidation, bilianic acid yields cilianic acid (LASSAR-COHN), whose form- 

 ula, according to PREGL, S is C 20 H 2 8O 8 . On reduction (by putrefaction) 

 MYLIUS obtained desoxycholic acid, C 2 4H 40 O 4 from cholic acid. 



On stronger oxidation it yields cholesterinic acid, which has not been carefully 

 studied, and finally phthalic acid, as maintained by SENKOWSKI, but not sub- 

 stantiated by BULNHEIM or PREGL. 4 On reduction with hydriodic acid and red 

 phosphorus, PREGL obtained a product which he considers as a mono-carboxylic 



fCH 2 

 acid, with the formula C 20 H 31 \ (CH 3 ) 2 . SENKOWSKI 5 obtained an acid with the 



ICOOH 



formula C 2 4H 40 O 2 , cholylic acid, on the reduction of the anhydride. 



As above-mentioned, PREGL 6 obtained, by the action of concen- 

 trated sulphuric acid upon cholic acid, a fluorescent substance which 

 he calls dehydrocholon. This is produced by oxidation, and at the same 

 time, water is eliminated. It has probably the formula C 24 H 38 O. Dehy- 

 drocholon is nitrated by nitric acid, while the cholic acid is not. From 

 this behavior, as well as from the determination of the molecular refrac- 

 tion and dispersion of both bodies, PREGL finds it probable that cholic 

 acid belongs to the hydrated carbocyclic compounds. This view has 

 received further support by PANZER/ who obtained a homologue of 

 benzene having the formula CnH 16 from a cholic acid derivate, the chole- 



1 The important researches of Strecker on the bile-acids may be found in Annal . d . 

 Chem. u. Pharm., 65, (57, and 70; Mylius, Ber. d. deutsch. chem. Gesellsch., 19. 



2 Ibid., 39. 



3 Hammarsten, Ber. d. deutsch. chem. Gesellsch., 14; Cleve, Bull. Soc. chim., 35; 

 Latschinoff, Ber. d. d. chem. Gesellsch., 15; Lassar-Cohn, Ber. d. d. chem. Gesellsch., 

 32; Pregl, Wien. Sitzungsber., Ill, 1902. 



4 Se"nkowski, Monatsh. f. Chem., 17; Bulnheim, Zeitschr. f. physiol. Chem., 25 

 which also contains the literature on cholesterinic acid. 



5 Mylius, 1. c.; Pregl, Pfliiger's Arch., 71; Se"nkowski, Monatshefte f. Chem., 19. 



6 Zeitschr. f. physiol. Chem., 45. 



7 Zeitschr. f. physiol. Chem., 48; Latschinoff, Ber. d. d. Chem. Gesellsch., 12 



