The constituents of the seeds of Casimiroa edulis / by Frederick B. Power and Thomas Callan.

  • Frederick Belding Power
Date:
1911
Catalogue details

Licence: In copyright

Credit: The constituents of the seeds of Casimiroa edulis / by Frederick B. Power and Thomas Callan. 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 Solid Acids.—These acids, when crystallised from glacial acetic acid, separated in glistening leaflets, melting at 60—62°: 0T030 gave 0 2875 CO, and 01194 H20. C = 761; H = 12*9. 0 2292 neutralised 00461 KOH. Neutralisation value=201’l. C10H3.,O2 requires C = 75 0; H = 12-5 per cent. N.V. = 2191. C^H^oj „ C = 761; H = 12'7 „ „ N.V. = 197*5. The solid acids would thus appear to consist of a mixture of palmitic and stearic acids, the latter predominating. Ethereal Extract of the Resin. This extract, after the removal of the solvent, formed a brittle mass, which could readily be reduced to a light brown powder, and amounted to 75 grams. It was heated with 2 litres of alcohol, when the greater portion dissolved. The small insoluble portion (2 3 grams) was collected, and identified as ipuranol. Isolation of a New Lactone, Casimirolid, C2.H2806. The above-mentioned hot alcoholic liquid deposited on cooling a quantity (22* 1 grams) of well-developed crystals, which, when recrystallised from alcohol with the addition of a little animal charcoal, separated in colourless prisms, melting at 229—230°: 0 0960 gave 0 2448 CO, and 0 0594 H,0. C = 69*5; H = 6*9. 0T326, in 2T16 benzene, gave M — 0-072°. M.W. = 426. C24H2806 requires C = 69*9; II = 6'8 per cent. M.W. = 412. From these results it is evident that the above-described substance possesses the formula C24H2S06, and that it is a new compound. Having ascertained that it is a lactone, as shown below, it is proposed to designate it casimirolid. Casimirolid is readily soluble in ether, chloroform, and ethyl acetate. It is optically active, and a determination of its specific rotatory power gave the following result: 0*3856, made up to 25 c.c. with chloroform, gave aD -1°31/ in a 2-dcm. tube, whence [a]D — 49*2°. Hydrolysis of the Lactone. Formation of a New Hydroxy-acid, Casimiroic Acid, C23H2804(0H)*C02H. When casimirolid is shaken with a cold solution of potassium hydroxide in aqueous alcohol, it readily takes up a molecule of water, and is converted into an acid, which is precipitated on acidifying the alkaline liquid. This acid crystallises very readily from alcohol in rosettes of glistening needles, melting at 207°: