T^EW York Agricultural Experiment Station. 16V 



proof whatever that either pyro- or metaphosphoric acid is present 

 in cottonseed meal. 



The purpose of the present investigation was to isolate and 

 identify, if possible, the organic phosphoric acid in cottonseed meal. 

 We are, consequently, unable either to deny or affirm the absence 

 or presence of pyro- or metaphosphoric acid in this product. We 

 have found, however, that the organic phosphoric acid isolated 

 from cottonseed meal gives all the reactions reported by the above 

 authors, which they considered as evidence of the presence of pyro- 

 and metaphosphoric acid. It seems, therefore, probable that the 

 reactions referred to are due to the organic phosphoric acid rather 

 than to pyro- or metaphosphoric acids. 



The preparation of the substance and its purification will be more 

 fully described in the experimental part. It will suffice to state 

 here that cottonseed meal was extracted with 0.2 per ct. hydrochloric 

 acid and the substance isolated as the barium salt. The purifica- 

 tion of the substance is very difficult. The extract contains large 

 quantities of soluble impurities, mucilaginous substances, proteins, 

 etc., which render the purification extremely difficult and tedious. 

 In addition to the above, there is apparently some carbohydrate 

 associated with the organic phosphoric acid, the removal of which 

 requires much time. For the same reasons the yield of the pure 

 product is very unsatisfactory. 



The compound finally obtained is very similar to phytic acid so 

 far as composition and reactions are concerned. In fact it is im- 

 possible, from the present data, to determine whether the sub- 

 stance is phytic acid or an isomer. Both yield inosite when 

 heated in a sealed tube with dilute sulphuric acid and the reactions 

 of aqueous solutions of the free acids can hardly be differentiated. 



The most striking difference is that the barium salt of the product 

 from cottonseed meal shows a decided tendency to crystallize, a 

 property which we have never observed when working with barium 

 phytate under the same conditions. 



If the substance from cottonseed meal is precipitated from acid 

 solutions with barium hydroxide it separates as a white amorphous 

 precipitate. When the dried precipitate is digested in 0.5 per ct. 

 hydrochloric acid it dissolves very readily but after a few minutes 

 it precipitates again. Under the microscope this precipitate is 

 seen to consist of balls or globular masses of very fine needle-shaped 

 crystals. The dilute hydrochloric acid solution of the barium salt 

 gives a white amorphous precipitate on the addition of alcohol; by 

 standing for several hours, however, it slowly assumes the same 

 crystalline form as mentioned above. The free acid is not precip- 

 itated by barium chloride but if such a solution is allowed to stand 

 over night or longer the barium salt will separate in fine needle- 

 shaped crystals, grouped in the same general form as above but the 

 individual crystals are much larger. The amorphous precipitates 



