The constituents of the bark of Prunus serotina : [isolation of 1-mandelonitrile glucoside] / by Frederick B. Power and Charles W. Moore.

  • Frederick Belding Power
Date:
[1909]
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The constituents of the bark of Prunus serotina : [isolation of 1-mandelonitrile glucoside] / by Frederick B. Power and Charles W. Moore. 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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    of considerable interest from the fact that, so far as known to us, it is the first instance in which its occurrence in nature has been observed. Further confirmation of the identity of the above substance was afforded by the preparation of some derivatives, a determination of the number of methoxyl groups, and its molecular weight. The methyl ester was prepared in the usual manner, and, as this can be volatilised with steam, it affords a ready method for the purification of the acid. When crystallised from water, it separated in long needles melting at 84° : 0-2098 gave 0-4485 C02 and 01190 H20. C = 58-3 ; H = 6-3. CnHu05 requires C = 58-4 ; H = 62 per cent. The acid was regenerated from this ester, and crystallised from ethyl acetate, when it melted at 167—169°, as before, and was again analysed : 0-1287 gave 0 2680 C02 and 0-0685 H20. 0 = 56-8 ; H = 5-9. C10H12O6 requires C = 56’6 ; H = 56 per cent. The silver salt was obtained as a crystalline precipitate by the addition of silver nitrate to a solution of the ammonium salt. It was washed with a little cold water, dried in a vacuum over sulphuric acid, and analysed : 05070 gave, on ignition, 0-1710 Ag. Ag = 337. C10HnO5Ag requires Ag = 33-8 per cent. A determination of the number of methoxyl groups in the acid by Perkin’s modification of the Zeisel method gave the following result : 0-1316 gave 0-4370 Agl. OMe = 43 8. C7H300(OMe)3 requires OMe = 43-9 per cent. The molecular weight of the acid was determined by the cryoscopic method in acetic acid solution : 0 2965 in 22-2415 of acetic acid gave M - 0-254°. M.W. = 201. C]0H12O5 requires M.W. = 212. Isolation of ip-Coumaric Acid. After the removal of the trimethylgallic acid from the ethereal liquid by the first three extractions of the latter with aqueous ammonium carbonate, as above described, the subsequent extractions with this alkali gave, when acidified, about 8 grams of a product melting at 210—213° with evolution of carbon dioxide. This was recrystallised from hot water, from which it separated in small, colour- less needles melting, as before, at 210—213° : 0-1580 gave 0-3810 C02 and 0-0690 H20. C = 65-8 ; H = 4-9, C9H8Oa requires C = 65*9 H = 4*9 per cent,