382 BILIFUSCIN. BILIHUMIN. BILIPRASIN. [BOOK II. 



Bilifuscin C 32 H 40 N 4 8 ? 



By this name Stadeler 1 designated a constituent of gall-stones 

 which, contrasted with bilirubin, is very sparingly soluble in chloro- 

 form, but is soluble in absolute alcohol. When bilirubin-calcium 

 gall-stones have been treated with hydrochloric acid and then 

 extracted with chloroform (see page 316), the first chloroform extract 

 contains some bilifuscin. When evaporated to dryness, the residue 

 yields the latter substance to absolute alcohol. The greater part of 

 the bilifuscin is to be found in the residue from which chloroform 

 has extracted bilirubin. If this be dried and treated with absolute 

 alcohol, the latter dissolves bilifuscin. The solution is evaporated to 

 dryness, extracted with boiling water, and the insoluble residue 

 again dissolved in as small a quantity as possible of absolute alcohol. 

 From its solution in the latter, the colouring matter is precipitated 

 by the addition of large quantities of ether. It is again dissolved in 

 alcohol and the solution evaporated to dryness. 



Bilifuscin is described as a dark-brown body easily soluble in 

 alcohol, glacial acetic acid, and solutions of the alkaline hydrates. It 

 is sparingly soluble in chloroform and is insoluble in water and ether. 

 Its solutions are brown, with a shade of olive-green. Its ammoniacal 

 solution is precipitated by calcium chloride, insoluble brown flakes of 

 bilifuscin-calcium being obtained. Bilifuscin does not exhibit Gmelin's 

 reaction. 



Bilihumin ? 



By this term is designated the insoluble colouring matter which 

 is left after decomposing bilirubin-calcium calculi with dilute hydro- 

 chloric acid and extracting with chloroform, absolute alcohol and 

 ether. The body, which is doubtless a mixture of derivatives of 

 bilirubin, does not exhibit Gmelin's reaction. 



Naunyn 2 seems to consider bilihumin to be almost a characteristic 

 of the small biliary calculi w T hich take their origin in the intra- 

 hepatic ducts, and which are to be distinguished from concretions of 

 inspissated bile by their containing the higher oxidation products of 

 the bile-colouring matter (to wit, biliverdin, bilicyanin and choletelin) 

 as well as bilihumin-like bodies. It is very hard to understand how 

 oxidations can take place within the hepatic ducts. 



Biliprasin ?? 



The colouring matter described under this name by Stadeler is 

 believed to be a mixture of bilifuscin and biliverdin. 



1 Stadeler, ' Ueber die Farbstoffe der Galle,' Annalen d. Chemie u. Pharm. 

 Vol. cxxxn. (1864), pp. 323 et seq. 



2 Naunyn, 'Die Entstehung der Bilirubin -Kalksteinchen in den Gallengangen der 

 Leber.' Op. cit. p. 27. 



