The constituents of the rhizome and roots of Caulophyllum thalictroides / by Frederick B. Power and Arthur H. Salway.

  • Power, Frederick B. (Frederick Belding), 1853-1927.
Date:
1913
Catalogue details

Licence: In copyright

Credit: The constituents of the rhizome and roots of Caulophyllum thalictroides / by Frederick B. Power and Arthur H. Salway. 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 number of acetyl groups in this sodium derivative was directly determined by heating the substance with a known volume of Nj 10-alcoholic sodium hydroxide, and titrating the excess of alkali with standard acid: 0 3191 gave on hydrolysis acetic acid equivalent to 8'45 c.c. N/ 10-NaOH. C0*CH3 = 1T4. C42Hc30GNa(CO*CH3)2 requires COCH3 = lll per cent. T etrab enzoylcaulosapog enin, —This com- jjound was prepared by heating caulosapogenin in pyridine solution with benzoyl chloride for about an hour. The mixture was then poured into water, rendered slightly alkaline with sodium carbonate, and kept for some time, when the reaction product slowly solidified. It was collected and purified by crystallisation from a mixture of chloroform and alcohol, when the substance separated in well- formed, hexagonal prisms, melting at 288°. An analysis and a determination of its molecular weight gave the following results: 01040 gave 0'2946 C02 and 0'0735 EUO. C = 77-3; H = 79. 0'5529 in 252 benzene gave ht — 0T02°. M.W. = 1076. C70H82O10 requires C = 77'6; H = 7'6 per cent. M.W. = 1082. The preceding results have thus served to establish the corrects ness of the formula assigned to caulosapogenin. Tetrabenzoylcaulosapogenin is readily soluble in ether, chloro- form, or benzene, but only sparingly so in water or alcohol. It does not possess the phenolic properties of the original substance. Its specific rotatory power was determined, with the following result: 0'3092, made up to 20 c.c. with chloroform, gave aD in a 2-dcm. tube, whence [o]D +11T00. Caulosapogenin Monomethyl Ether, C42H6506(0*CH3).—This sub- stance was prepared by heating caulosapogenin for several hours with alcoholic sodium hydroxide and methyl iodide. When crystal- lised from dilute alcohol, it separated in well-formed needles, melt- ing at 235°: 0-1143 gave 0'3173 C02 and 0T059 H20. C = 75'7; H = 10‘3. The number of methoxyl groups in the compound was determined by Perkin’s modification of Zeisel’s method: 0-1318 gave 0-0544 Agl. MeO = 5‘5. C42H6505(0Me) requires C = 75‘9; H=100j MeO = 4’6 per cent. The specific rotatory power of the substance was determined with the following result: 0-1412, made up to 20 c.c. with chloroform, gave aD +1°3' in a .A-dcm. lube, whence [a]D +744°.