Note on gynocardin and gynocardase / by Charles W. Moore and Frank Tutin.

  • Moore, Charles Watson.
Date:
1910
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: Note on gynocardin and gynocardase / by Charles W. Moore and Frank Tutin. 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.

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    the barium with sulphuric acid. It was observed by the present authors that when a considerable excess of barium hydroxide is employed in the hydrolysis a very sparingly soluble crystalline double compound of barium gynocardinate and barium hydroxide separates, but this was not further investigated. Twenty grams of gynocardinic acid were methylated by means of methyl iodide and dry silver oxide according to Purdie and Pitkeathly’s method (loc. cit.). The methylation was first carried out in methyl alcohol solution, and was repeated under these con- ditions until the product was soluble in methyl iodide, after which further methylation was effected in methyl iodide solution, the treatment being continued until there was no further reaction on boiling with dry silver oxide. The methylated product was removed from the reaction mixture by means of ether. It formed a syrup, which showed no signs of crystallising. When distilled under diminished pressure, a definite fraction boiling at 220°/15 mm. was obtained, which formed a viscid liquid at the ordinary temperature: 0 1642 gave 0'3170 COg and 0'1145 H2O. C = 52 6j H = 7'7. C10H32O11 requires C = 52'3; H = 7 3 per cent. A determination of the number of methoxyl groups by Perkin’s modification of Zeisel’s method gave the following result: 0-1880 gave 0‘6010 Agl. OMe = 42-2. Ci3Hi405(0Me)6 requires OMe = 42'6 per cent. This substance is therefore a methyl ‘pentamethylgynocardinaie, C]2Hj404(0Me)5C02Me, and must therefore still contain two hydroxyl groups, since Power and Lees have shown that gynocardin yields a hepta-acetyl derivative. In the endeavour to obtain a fully methylated product, a small quantity of the ester was heated with methyl iodide and dry silver oxide for some hours at 100° in a sealed tube, but the product gave practically the same results on analysis as before this treatment. On boiling methyl pentamethylgynocardinate with dilute sul- phuric acid, it was completely decomposed, nothing but bro-wn, resinous products resulting. Sodium Derivative of Gynocardin, CjaHigOaNNa. As already mentioned, gynocardin possesses feebly acidic pro- perties, in virtue of which it is able to form derivatives with the alkali metals. On adding excess of sodium ethoxide or aqueous sodium hydroxide to an ethyl-alcoholic solution of gynocardin, a white precipitate is produced, readily soluble in water or methyl alcohol, but sparingly so in ethyl alcohol;