N. 0. BlXINE^l. 123 



and isolinolenic acids, the lattter preponderating ; and (4) oleic acid, in 

 relatively small amount. 



In addition to the fatty oil, gynocardia seeds contain 5 per cent, of a 

 crystalline glucoside, gynocardia, C 12 H 19 9 N, l£H 2 0, and a hydrolytic enzyme, 

 gynocardase. 



(Power and Barroncliff, Trans., Oh. S. LXXXVII, p. 896, et seq.) 



Gynocardin, a new cyanogenetie glucoside. Power and Gornall have 

 (shown Ohem. Soc. Proc, 1904) that when the seeds of Gynocardia odorata 

 are crushed and brought into contact with water, hydrogen cyanide is 

 formed, owing to the presence in the seeds of a cyanogenetie glucoside, 

 which was isolated and designated gynocardin. They have determined its 

 constitution. Four Kilos of the powdered gynocardin seeds were first extracted 

 with cold petroleum, for the complete removal of the fatty oil, and then with 

 25 per cent, alcohol. On expelling the alcohol from the extract, a dark syrupy 

 residue was obtained, which soon formed a paste consisting chiefly of a 

 crystalline substance ; this was separated from the mother-liquor, digested 

 for several minutes with warm ethylacetate, and again separated. A further 

 quantity of the crude glucoside was obtained from the syrupy alcoholic 

 mother-liquor, by first mixing it with " prepared saw dust," drying the mass 

 and extracting it with ethylacetate, which slowly removes the glucoside. 

 The crude glucoside was purified by dissolving it in water, treating the solu- 

 tion with animal charcoal, and evaporating under diminished pressure to a 

 syrup, which set to a hard cake of colourless crystals which were dried on 

 porous earthenware. The yield was 200 grams. Gynocardia forms colourless, 

 glistening, prismatic needles of thecompositien C 13 H 10 O 9 N-f HH 2 ; the water 

 is expelled at 115°0. The anhydrous compound melts at 162°-163°C, and has 

 the optical rotation (a) D2l°=+72 , 5° in aqueous solution. It is readily 

 hydrolysed at the ordinary temperature by gynocardase ; an enzyme 

 contained in the seeds, but only with difficulty by boiling with 5 per cent, 

 hydrochloric or sulphuric acid. Dextrose and hydrogen cyanide were isolated 

 from the products of the reaction, but the third substance, C 6 H 3 4 , which 

 should be produced, according to the equation : — 



C ;3 H 19 O 9 N+H 2 O=C -H 12 O -+C 6 H 8 O 4 +HON, is decomposed by secondary 

 reactions. Gynocardin differs from other known cyanogenetie glucosides in 

 its relatively great stability towards acid hydrolysing agents. It is hydro- 

 lysed by treatment with barium hydroxide solution, ammonia and the barium 

 salt of gynocardic acid C 12 H, 9 9 C0 2 H, being formed, according to the 

 equation : C 13 H 19 9 N+2H 2 0=C 12 H 19 9 .Co 2 H4-HN 3 . This acid forms dextrose 

 and an acid, C 7 H 10 O o -, on hydrolysis with acids. The results obtained indicate 

 that gvnocardia is the dextrose either of the cyanohydrin of a trihydroxj— 

 aldehde or ketone, in accordance with one of the following formulae : 



C,H 4 (OH 3 .CH(CN)O.C 6 H n 5 , or 



C 5 H a (OH) 3 C(CN), O.C -H u O^ 



The enzyme gynocardase was isolated by treating the finely-ground seeds 



with light petroleum to remove the fatty oil, and then digesting them with 



water, at the ordinary temperature, for 24 hours. The filtered liquid was 



treated with twice its volume of alcohol, and after standing for some hours, 



