SECTION III, 1902 11178] Trans. R.S, C. 
XIIL.— An Abnormal Result in the Hydrolysis of Amygdaline. 
By J. WALLACE WALKER, M.A., Ph.D. 
AND 
W. S. Hurcurnson, M.Sc. 
(Read May 27, 1902.) 
The glucoside amygdaline C,,H,,NO,,, as is well known, when 
heated with dilute acids, is split up into glucose, benzaldehyde and 
hydrocyanie acid, the reaction consisting in a combination of the 
substance with the elements of water. When amygdaline is treated 
with strong hydrochloric acid at a temperature of 100° C. for two 
hours the glucose is converted into a charred mass, and the aqueous 
extract contains ammonium chloride and laevo-rotatory mandelic 
acid. One of us has had occasion to convert large quantities of 
amygdaline into active mandelic acid by the above method, but the 
yield was always much below the theoretical. A somewhat larger 
quantity was obtained by using hydrochloric acid of specific gravity 
1:12. The loss was not due to the production of the inactive variety, 
although the formation of the latter might, from analogy with the 
behaviour of tartaric and malic acids under similar conditions, be 
expected on heating the active with a strong mineral acid. As 
amygdaline is an exceedingly expensive substance it was thought 
advisable to try the hydrolysis in another way. | 
When amygdaline is boiled with alkalies the nitrogen atom only 
is split off as ammonia, but the glucose is not separated from the 
remainder. It remains combined in the form of an acid called amyg- 
dalinic acid, a quantitative yield of the latter being obtained, and it 
was expected that the substance could then be resolved quantitatively 
into glucose and active mandelic acid by boiling with dilute hydro- 
chloric acid. The first part of the expectation was fulfilled, the 
reaction went quantitatively, but instead of active mandelic acid, the 
inactive modification was alone produced. 
The method we adopted was to boil the amygdaline with a slight 
excess of barium hydroxide solution till all the ammonia was expelled, 
then add enough normal hydrochloric acid to combine with all the 
barium, and leave a gram molecule in excess for every gram molecule 
of amygdaline taken. This solution was then boiled for six hours 
on the water-bath, polarimetric readings being taken every hour till 
there was no further change in rotation. When cold, it was extracted 
with ether. The ether left on evaporation a crystalline acid which, 
