Gynocardin : a new cyanogenetic glucoside / by Frederick B. Power and Frederic H. Lees.

  • Frederick Belding Power
Date:
[1905]
Catalogue details

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.

    9/16 (page 355)
    mixture of ethyl acetate and light petroleum, then from a mixture of chloroform and petroleum, and finally from the former mixture of solvents, without any appreciable change in the melting point. Hepta-acetylgynocardin forms aggregates of fine, white needles melt- ing at 118—119°. 0-1532 gave 0-2907 C02 and 0-0736 H20. C = 51 -8 ; H = 5’3. 0-1672 „ 0-3180 C02 „ 0-0808 H20. C = 51-8; H = 5-4. C13H1209(C2H30)7N requires C = 51’7 ; H = 5-3 per cent. A solution of 0-4740 in chloroform, made up to 25 c.c., gave, in a 1 dm. tube, aD + 0°46', whence [a]D + 40-4°. Hydrolysis of Gynocardin by Dilute Acids. The Formation of d -Glucose. Gynocardin is only very slowly hydrolysed by heating with 5 per cent, hydrochloric or sulphuric acid, and the reaction is always attended with the formation of a dark secondary product, even when the operation is conducted in an atmosphere of carbon dioxide. In experiments in which two portions of gynocardin of 10 grams each were heated, in the one case for 2 hours on a water-bath with 100 c.c. of 5 per cent, hydrochloric acid, and in the other by boiling for 4 hours with 5 per cent, sulphuric acid, it was possible to recover some unchanged gynocardin, hydrolysis having been far from complete, even with these prolonged periods of heating. The following experiment represents the result of the complete hydrolysis of gynocardin with hydrochloric acid. Twenty grams of gynocardin were dissolved in 200 c.c. of 5 per cent, hydi’ochloric acid and the solution heated on a water-bath. Hydrogen cyanide was not present in the liquid until the heating had been in progress for half an hour. After 7 hours’ heating, when the solution smelt strongly of hydrogen cyanide and had become brown in colour, steam was passed through it. It then became apparent that hydrolysis had not been complete, for it was necessary to continue the distillation until 2A litres of liquid had collected before all the hydrogen cyanide was removed. The residual liquid, which contained the non- volatile products of the completely hydrolysed glucoside, was very dark brown, considerable secondary decomposition appearing to have taken place. This solution was neutralised with sodium hydroxide, concen- trated considerably under diminished pressure, and extracted with ether, but nothing was removed by the latter. It was therefore mixed with previously extracted sawdust, the mass dried, and extracted with ether, ethyl acetate, and ethyl alcohol respectively. The ether and ethyl acetate extracted nothing, but from the alcoholic extract there