N. 0 BIXINEjE. 
123 
and isolinoleuic acids, the lattter preponderating; and (4) oleic acid, in 
relatively small amount. 
In addition to the fatty oil, gyuocardia seeds contain 5 per cent, of a 
crystalline glucoside, gynocardia, C ll H 13 O i) N, IJH,0, and a hydrolytic enzyme, 
gynocardase. 
(Power and Barroncliff, Trans., Ch. S. LXXXVH, p. 898, et seq.) 
Gynocardin, a new cyanogenetie glucoside. Power and Gornall have 
(shown Ohcm. Soc. Proc., t904) that when the seeds of Gynocardia odorata 
are crushed and brought iuto 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 the composition JH 2 0 ; the water 
is expelled at 115°C. 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 percent, 
hydrochloric or sulphuric acid. Dextrose and hydrogen cyanide were isolated 
from the products of the reaction, but the third substance, C 5 H 9 0 4 , which 
should be produced, according to the equation : — 
C 13 U, # 0 9 N - t -Il 2 0=C 5 iI I7 O d -f 0,11,0, -j 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^H^OjCO^H, being formed, according to the 
equation : C 1J H 1> 0,N+2H I 0.=0 11 H, i) O a .Co 1 H+HNj. This acid forms dextrose 
and an acid, C 7 II 10 O o ., on hydrolysis with acids. The results obtained indicato 
that gynocardia is the dextrose either of the cyanohydrin of a trihydroxy— 
aldehde or ketone, in accordance with one of the following formulae : 
OiH^OHj.OI^CNJO.CjHjjOj, or 
C s H s (OH), C(CN), O.C s H n O s . 
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, 
