CLE A VA GE PR OD UCTS OF THE BILE A CIDS. 3 8 1 
therefore contain one carboxyl group (COOH), and according fco Mylius 1 
it also contains one secondary (CHOH) and two primary alcohol 
groups (CH 2 OH). 
The evidence for this is derived from its behaviour on cautious 
oxidation. It first yields, when oxidised, monobasic dehydrocholalic acid 
(( '. J( 1 1 ..,< ).),- and on further oxidation tribasic bilic, or bilianic acid 
(C 24 H., 4 8 ). 3 These changes may be expressed by supposing that, in 
the formation of dehydrocholalic acid, the two primary alcohol groups 
form aldehyde groups (H — C = 0), and the secondary group, a ketone 
group (C = 0), and that in the further formation of bilianic acid the two 
aldehyde groups pass into (acid or) carboxyl groups, so producing a 
tribasic acid ; while besides, in the rest of the molecule, an additional 
ketone group is formed, as shown by the following formulae : — 
Cholalic acid, C 20 H 31 (CHOH)(CH 2 OH) 2 (COOH), n oxidation forms, 
in place of one secondary alcohol group (CHOH) and two primary 
alcohol groups (CH 2 OH), one ketone group (CO) and two aldehyde 
groups (COH), thus yielding dehydrocholalic acid, C 20 H 31 (CO)(COH) 2 
(COOH), in which, on further oxidation, an additional ketone group is 
formed, and the aldehyde groups change into carboxyl groups (COOH), 
thus yielding the tribasic acid, bilianic (or bilic) acid, C 19 H 31 (CO.) 2 (COOH) 3 . 
Scarcely anything is known of the arrangement of the atoms in the 
hydrocarbon part of the molecule. Mylius 4 has obtained a reaction 
between cholalic acid and iodine, in solution, with the formation of a 
blue compound, which is crystallisable and becomes easily dissociated in 
the same manner as iodide of starch. For example, in solution, it 
becomes decolorised on heating. 
This substance is probably an addition product of cholalic acid and 
iodine, and so points out that the hydrocarbon radicle of the acid is not 
fully saturated ; beyond this, however, we know nothing of its composition. 
Desoxycholalic acid is a reduction compound obtained by Mylius 5 of 
the formula C 24 H 40 O 4 . 
Clioleic acid 6 was first found in the preparation of cholalic acid from ox 
bile, and separated from it by means of the more sparing solubility of its barium 
salt. According to Lassar-Cohn, it also occurs in human bile, and its formula 
is C 24 H 4 „0 4 . Latscbinoff, 7 its discoverer, ascribed to it the formula C 25 H 42 4 . 
From Lassar-Cohn's 8 formula it appears to be isomeric, or perhaps identical, 
with desoxycholalic acid. 
Fellic acid 9 (C 2 oH 40 O 4 ) is an arid which has been obtained from human 
bile ; it is crystalline, insoluble in water, and forms insoluble barium and 
magnesium salts. 
The acids formed by the cleavage of the peculiar bile acids found in the bile 
of the pig and goose have been already mentioned in treating of these acids. 
1 Ber. d. deutsch. chem. Gesellsch., Berlin, 1886, Bd. xix. S. 369, 2000. 
2 Hammarsten, ibid., 1881, Bd. xiv. S. 71 (iJchydrocholsaiire) ; Lassar-Colm, ibid., 1892, 
Bd. xxv. S. 805 ; Ztschr. f. physiol. Chem., Strassburg, 1892, Bd. xvi. S. 488. 
3 Clevo, Bull. Soc. chim., Paris, tome xxxv. 
4 Ztschr.f. physiol. Chem., Strassburg, 1887, Bd. xi. S. 306 ; Ber. d. deutsch. chem. 
Gesellsch., Berlin, 1887, Bd. xx. S. 683. 
5 Loc. eit. 
6 Choleinsdure of Latscbinoff, Ber. d. deutsch. chem. Gesellsch., Berlin, 18S5, Bd. xviii. 
S. 3039. 
7 Loc. cit. 
8 Ber. d. deutsch. chem. Gesellsch., Berlin, 1894, Bd. xxvii. S. 1339. 
9 Fellinsaure of Schotten, Ztschr. f. physiol. Chem.. Strassburg, 1887, Bd. xi. S. 26S. See 
also Lassar-Cohn, ibid., 1894, Bd. xix. S. 563. 
