The constituents of the leaves of prunus serotina / by Frederick B. Power and Charles W. Moore.

  • Frederick Belding Power
Date:
[1910?]
Catalogue details

Licence: In copyright

Credit: The constituents of the leaves of prunus serotina / by Frederick B. Power and Charles W. Moore. Source: Wellcome Collection.

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    sodium carbonate, when an insoluble compound was deposited, which was evidently the sodium salt of an acid phthalic ester. This was collected, washed with a little ether and water, and then hydrolysed by boiling for some time with an alcoholic solution of potassium hydroxide. On cooling, a quantity of a colourless sub¬ stance separated, which was collected, washed with a little alcohol, and crystallised from a large volume of alcohol, when it was obtained in colourless, glistening plates, melting at 79°. (Found, C = 81’5; H = 14'l. Calc., C = 81*8; H = 14*l per cent.) This substance was thus identified as ceryl alcohol. The ether-chloroform solution from which the ceryl alcohol had been removed, as above described, was evaporated, and the residue heated with alcoholic potassium hydroxide in order to hydrolyse unchanged phthalic anhydride. The alcohol was then evaporated, water added, and the insoluble portion extracted with ether, the ethereal liquid being washed, dried, and the solvent removed. A quantity of a waxy solid was thus obtained, which distilled between 170° and 300°/15 mm., but from which no pure substance could be isolated. It appeared to consist of a mixture of hydrocarbons. Isolation of Ipuranol, C23H3802('0H)2. The aqueous, alkaline solution of potassium salts, from which the hentriacontane and ceryl alcohol had been removed by extrac¬ tion with ether, was acidified, and again extracted with ether. The ethereal liquid was washed, dried, and concentrated to a volume of about 500 c.c., when, on keeping for several hours, a small quantity of a dark green powder separated. This was collected, washed with ether, and crystallised from dilute pyridine, when it was obtained in colourless, microscopic needles, melting at 295°. This substance possessed the characteristic properties of ipuranol (Trans., 1909, 95, 249), with which it evidently was identical. It yielded an acetyl derivative, which separated in glistening leaflets, melting at 163°, and when this was mixed with a little diacetyl- ipuranol the melting point remained unchanged. The amount of substance obtained was too small for analysis. Examination of the Fatty Acids. The ethereal filtrate from the ipuranol was concentrated some¬ what, and then mixed with a large volume of light petroleum, when a quantity of chlorophyll was precipitated. This was removed by filtration, and the filtrate evaporated, when a quantity (12 grams) of fatty acids was obtained, which, when distilled under diminished pressure, passed over between 225° and 237°/12 mm.
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