110 PROTEIN POISONS 



Likewise a heavy precipitate is produced by the use of a 

 saturated solution of picric acid, but the poison is not in the 

 precipitate, which gives only a very poor Millon test after 

 removal of the picric acid, and no biuret. Hofmeister has 

 given a method for introducing iodine into the molecule 

 of egg albumen. This was tried with the poison split from 

 egg albumen. The iodized compound no longer gave either 

 the Millon or biuret reactions, and while it affected animals 

 more or less, they did not die, and the symptoms were not 

 those induced by toxin poisoning. The iodine seemed to 

 have entered into chemical combination in the poison 

 molecule, and to have thus changed its characteristics. 

 The iodized body was freely soluble in absolute alcohol, 

 and in alkaline water, not in water alone, and was precipi- 

 tated by acid water from alcoholic solution, also on acidi- 

 fying an alkaline water solution. Though it no longer 

 responded to the Millon and biuret reactions, a good test 

 for nitrogen was obtained after fusing with metallic sodium. 

 An attempt was made to benzoylate the poison by the 

 Schotten-Baumann method, using albumin poison. Prac- 

 tically no precipitate was obtained. From the filtrate in a 

 part soluble in hot alcohol there were obtained shiny, glis- 

 tening plates or flat needles which matted together under 

 suction, and had much the appearance of some of the fatty 

 acids. These were insoluble in water or very difficultly 

 so, if at all, difficultly soluble in cold alcohol, readily in hot. 

 They gave no Millon test, no biuret, no Molisch, and con- 

 tained no nitrogen. After recrystallization from alcohol 

 they melted constantly at 62. Palmitic acid melts at 62 

 and boils at 339 to 350 (Mulliken). A Merck preparation 

 of palmitic acid melted at 62 and boiled at about 345 to 

 350. Our crystals had not yet boiled at 360, though 

 above 300 there was some decomposition. From the 

 remainder of the filtrate there was obtained from the part 

 soluble in cold alcohol a non-crystallizable body, giving 

 both Millon and biuret tests and containing 9.335 per cent, 

 of nitrogen, and from the part soluble only in water, likewise 

 a non-crystalline compound, with 9.66 per cent, nitrogen, 



