366 Report of the Department of Chemistry of the 



phoric acid. It is likewise carried down in the precipitate obtained 

 with copper acetate because copper oxalate is very slightly soluble. 

 The complete removal of the barium oxalate from the other mixture 

 of barium salts was finally secured by allowing it to crystallize out 

 from a very dilute hydrochloric acid solution of the mixed salts. 



If the name " phytin " is to be applied to certain salts of inosite 

 hexaphosphate then it is evident that wheat bran does not contain 

 phytin for we have been unable to isolate any salt of this acid from 

 this material. 



It appears more probable that wheat bran contains several different 

 organic phosphoric acids. So far we have been able to identify 

 only one of these acids, viz., inosite monophosphate, a substance 

 which will be described in a succeeding paper. 



EXPERIMENTAL PART. 



ISOLATION OF THE CRUDE ORGANIC PHOSPHORUS COMPOUND FROM 



WHEAT BRAN. 



A larger quantity of the crude natural organic phosphorus com- 

 pound was prepared by precipitating a 0.2 per ct. hydrochloric 

 acid extract of wheat bran with alcohol exactly as before. From 

 25 kilograms of wheat bran we obtained 222 grams of the crude 

 compound as a nearly white amorphous powder. This substance 

 had the following composition: C = 20.21; H = 3.54; P = 13.45; 

 Mg = 8.20; K = 5.23; Na = 2.56; Ca = trace. Nitrogen was present 

 but it was not determined. The substance was practically free 

 from inorganic phosphate as it gave only a trace of a yellow precipi- 

 tate on warming its nitric acid solution to 65° for a longer time with 

 ammonium molybdate. 



Of the above substance, 50 grams were suspended in a small 

 amount of water and dissolved by the addition of a little hydro- 

 chloric acid. After diluting with water it was precipitated by adding 

 barium hydroxide in excess. It was then filtered and thoroughly 

 washed in water. 



PREPARATION OF THE NITROGEN-CONTAINING SUBSTANCE. 



The filtrate from the above was freed from excess of barium 

 hydroxide with carbon dioxide, filtered and evaporated in vacuum 

 at a temperature of 40°-45° to small bulk and again filtered from a 

 small amount of barium carbonate. The concentrated solution was 

 then poured into about 500 c.c. of alcohol. It separated as a some- 

 what sticky mass which soon hardened. It was filtered, washed in 

 alcohol and ether and dried in vacuum over sulphuric acid. It 

 weighed 7 grams. 



It was dissolved in a small amount of water and reprecipitated 

 with alcohol, filtered, washed and dried as before. It was obtained 

 as a nearly white amorphous powder. The substance was very 



