I9I5] 



Casimir Funk 3^7 



used by Gautier and Mourgues ; and the extract was worked up by 

 ordinary methods for the Separation of organic bases. In the sec- 

 ond case the oil was extracted with dilute sulfuric acid sol., and the 

 phosphotungstate precipitate obtained was worked up by the acetone 

 method— which has been used successfully in our work on yeast (5) . 

 Substances were separated in each fraction, but the quantity of each 

 product was so small that the work will have to be repeated with 



more material. 



ExPERiMENTAL. I. The cod-Hver oil was entirely soluble in 

 ether, acetone, ligroin and Chloroform, and partially so in benzene. 

 With alcohol alone, or with alcoholic mercuric chlorid sol., a slight 

 precipitate was noticed. About 23.5 k. of the oil were used. Each 

 k. was extracted with a sol. of 660 cc. of abs. alcohol and 50 cc. of 

 conc. hydrochloric acid made up to 2 1. with water. Each k. was 

 extracted three times, a third part of the sol. having been used in 

 each extraction. The extracts were isolated in a separatory funnel, 

 and evaporated in vaciio. The residue, which had an agreeable 

 smell, was dissolved in alcohol, filtered from a precipitate which 

 consisted mainly of inorganic salts, and the sol. evaporated again. 

 Oil separated, which was twice washed with water and then hydro- 

 lyzed with 5 percent sulfuric acid sol. The watery extract was 

 precipitated with 5 percent sulfuric acid sol. containing 50 percent 

 of phosphotungstic acid. The precipitate was filtered, washed with 

 dilute sulfuric acid sol., and dried. It weighed 969 gm. when 

 nearly dry. 



Treatment of the phosphotungstic acid precipitate. The precip- 

 itate was decomposed with 2 k. of baryta in a mortar. The phos- 

 photungstate of barium was suspended in water and shaken. The 

 combined filtrates were freed from baryta with sulfuric acid and 

 evaporated in vacuo. The residue did not give a precipitate with 

 alcoholic mercuric chlorid sol. No precipitate was obtained with 

 silver nitrate and baryta. The sol. was freed from silver and 

 baryta, and was reprecipitated with phosphotungstic acid. The 

 resulting precipitate amounted to only 304 gm., consequently con- 

 siderable decomposition of the nitrogenous substances must have 

 taken place. This view is strengthened by the fact that the precip- 

 itate, decomposed with neutral lead acetate, gave a very heavy pre- 



