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.

    7/22 (page 247)
    The acetyl derivative, when crystallised from acetic anhydride, separated in needles melting at 118—119°. 0-2160, dissolved in 25 c.c. of chloroform, gave aD - 0°34' in a 2-dcm. tube, whence [a]D - 32,8°. The above-mentioned phytosterol was tested for the presence of stigmasterol, C30H50O, according to the method described by Windaus and Hauth (Ber., 1907, 40, 3681), and was found to be free from the latter compound. The melting point of its acetate would indicate that it is not identical with sitosterol (Zeitsch. physiol. Chem., 1902, 34, 461), but it agrees closely in its character with the phytosterol obtained from olive bark (Trans., 1908, 93, 909). Identification of the Fatty Acids. The alkaline, aqueous solution of potassium salts from which the phytosterol had been removed by extraction with ether, as above described, was acidified, and again extracted with ether, the ethereal solution being washed, dried, and the solvent removed. A quantity (12 grams) of fatty acids was thus obtained, which, when distilled under diminished pressure, passed over between 215° and 270°/10mm. As these acids distilled within the same range of temperature as those previously obtained, which existed in the bark in a free state, for the purpose of their examination the two portions were mixed. Twenty grams of the total mixed acids were converted into their lead salts, and the latter digested with ether, when a portion was dissolved. Both the soluble and insoluble portions were decomposed by hydrochloric acid, and the regenerated fatty acids purified by distillation under diminished pressure, when in each case they amounted to about 8 grams. The acids obtained from the soluble portion of lead salt were liquid, whilst those from the insoluble portion were solid. The Liquid Acids.—These acids were fractionally distilled under diminished pressure, and the following fractions collected: (a) 214—216° (about 5 grams) ; (b) 216—230°/12 mm. (about 2 grams). They were analysed and their iodine values determined, with the following results : (a) 0-1730 gave 0-4855 C02 and 0-1784 H20. C = 76-5; H = ll-4. 0-4190 absorbed 0-6312 iodine. Iodine value = 150-6. {b) 0-1890 gave 0*5360 C02 and 0-1930 H20. C = 77 3 ; H = ll-3. 0-2152 absorbed 0-3372 iodine. Iodine value = 156-7. ^i8H8402 requires C = 76-6 ; H = 12*1 per cent. Iodine value = 90-1. Ci8HsA „ C = 77-l j 11 = 11-4 „ „ =181-4. These results indicated that the liquid acids consisted chiefly of a mixture of oleic and linolic acids, the latter predominating.