306 



DERIVATIVES OF CHOLALIC ACID. 



[BOOK ii. 



2. Bilic Acid, C^H^Os. By the action of potassium dichro- 

 mate and sulphuric acid on cholalic acid Cleve 1 obtained bilic acid 

 an acid which is devoid of bitter taste, which does not exhibit 

 Pettenkofer's reaction, which is sparingly soluble in water but readily 

 soluble in alcohol, and separates from its alcoholic solutions in 

 crystals belonging to the rhombic system. Its specific rotation 



structural According to Mylius cholalic acid may be repre- 



formuia of sented by the formula, 

 cholalic acid / CHOH 



SiSTC: C 20 H 21 (CHOH) 2 



drocholalic 



acid and toilic Thig f ormu i a does not attempt to explain the structure 

 of the nucleus of cholacic acid, but to indicate that 

 cholalic acid is a monobasic acid in which are two primary 

 alcohol groups and one secondary alcohol group. The hypothetical 

 relation according to Mylius 2 between cholalic acid and its derivatives 

 is exhibited in the three subjoined structural formulae (Mylius, 

 slightly modified by Neumeister 3 ) : 



Cholalic acid. 



C 24 H 40 5 



Dehydrocholalic acid. 



Bilic acid. 



C 24 H 34 O 8 

 COOH 



COOH 



COOH 



CH 



OH 



c 



C 20 H 31 



CH 2 OH 



CHOH 



u o 



i, 



COOH 



C 19 H 31 COOH 

 CO 



CO 



Desoxychoia- From bile which had been decomposed by the 

 lie acid, a pro- ac ti on o f putrefactive bacteria, Mylius 4 separated, in 



reduction of addition to cholalic acid, an acid with the composition 

 cholalic acid. C^H^O^ to which he assigned the name desoxy cholalic 

 acid, indicating that it differs from cholalic acid in 

 containing less oxygen. He also obtained this acid by causing 

 sodium cholalate to digest for some days at about 40 C. with decom- 

 posing pancreas. 



1 P. T. Cleve, ' Sur les produits d'oxydation de 1'acide cholalique.' Bull. Soc. 

 Chimique, Vol. xxxv. 373379, 429438. Abstracted in Maly's Jahresbericht, Vol. xi. 

 (1882), p. 316. The Author has not seen the original. 



2 Mylius, <Ueber die Cholsaure.' Ber. d. d. chem. Gesellsch. Vol. xx. p. 19G8 et seq. 



3 Neumeister, Lehrbuch der physiologischen Chemie, Erster Theil, 1893, see p. 162. 



4 Mylius, ' Ueber die Cholsaure. ' 



