Gynocardin : a new cyanogenetic glucoside / by Frederick B. Power and Frederic H. Lees.
- Frederick Belding Power
- Date:
- [1905]
Licence: Attribution 4.0 International (CC BY 4.0)
Credit: Gynocardin : a new cyanogenetic glucoside / by Frederick B. Power and Frederic H. Lees. Source: Wellcome Collection.
Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.
5/16 page 351
![with 5 per cent, hydrochloric acid, and complete hydrolysis was not effected until the solution had been heated for 9 hours. During the hydrolysis, hydrogen cyanide is generated, and the solution continually becomes darker in colour, being ultimately dark brown. Among the products of the reaction, it has been possible to identify only (Z-glucose and hydrogen cyanide, although, excluding the contingency of secondary decomposition, which undoubtedly occurs, it should have been possible to obtain, in addition to the above hydrolytic products, a substance of the formula C6Hg04, in accordance with the equa- tion : C13H]909N + H20 = C6H1206 4- C6Hs04 + HCN. In view of the above-mentioned secondary decomposition, which was thought to be due solely to the prolonged heating necessary to effect hydrolysis, the enzyme, gynocardase, appeared to be better adapted for this purpose. Gynocardin is very readily hydrolysed at the ordinary temperature by the enzyme, but, as in the case of the hydrolysis by acid, the reaction is attended with the formation of dark-coloured resinous matter, and only glucose and hydrogen cyanide could be identified among the products. Gynocardin readily reacts with hot barium hydroxide, with the liberation of ammonia and the formation of barium gynocardinate, (C12H1909*C02)2Ba, according to the equation : C13H1909N + 2H20 = C12H1909-C02H + NH3. Gynocardinic acid, C12H1909’C02H, prepared from its barium salt, is extremely soluble in water, and was only obtained as a nearly colourless syrup; it is dextrorotatory, and does not reduce Fehling’s solution. When gynocardinic acid is heated with dilute sulphuric acid, it is hydrolysed in accordance with the equation : c12h19o9-co2h+h2o=c6h12o6+c6h9o4-co2h. There are formed, d-glucose (phenylglucosazone, m. p. 205—206°) and an acid, which must have the formula C7H10O6. This acid could not be separated in a free state from the sugar which accompanied it, but by converting it into its quinine salt a small amount of the latter could be isolated in a state of purity. This salt formed needles, melting at 224° with decomposition, and on analysis gave numbers agreeing fairly well with the formula C20H24O2N„,C7H10OG. The facts from which we draw a conclusion respecting the structure of gynocardin are as follows : (1) It has the formula C13H19O0N. (2) It gives a hepta-acetyl derivative.](https://iiif.wellcomecollection.org/image/b22401945_0007.jp2/full/800%2C/0/default.jpg)
