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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    Caulophyllosapogenin Dimethyl Ether, CMH8607(0,CHa)2.—In order to prepare this derivative, caulophyllosapogenin was dissolved in alcohol containing a little potassium hydroxide, and the solution heated with an excess of methyl iodide for slveral hours. The greater portion of the solvent was then removed, the mixture poured into dilute hydrochloric acid, and the resulting precipitate collected. When crystallised from dilute alcohol, it separated in stellate clusters of small needles, which melted at 240—242°: 0-0888 gave 0'2436 C02 and 0-0809 H20. C = 74‘8; H = 10T. The number of methoxyl groups in the compound was determined by Perkin’s modification of Zeisel’s method: 0-1547 gave 00.746 Agl. MeO = 64. C56H8607(OCH3)2 requires C = 74'7; H = 99; MeO = 6'7 per cent. Gaulophyllosapogenin dimethyl ether is readily soluble in alcohol, ether, chloroform, or benzene. Its specific rotatory power was determined with the following result: 0-1222, made up to 20 c.c. with chloroform, gave aD +0°32/ in a 2-dcm. tube, whence [a]D +436°. Identification of l-Arabinose, a Hydrolytic Product of Caulophyllosapogenin. The aqueous liquid obtained in the hydrolysis of caulophyllo- sapogenin, as above described, was exactly neutralised with sodium carbonate, and evaporated to dryness under diminished pressure. The residue was then digested with hot alcohol, the mixture filtered, and to the hot filtrate an equal volume of ethyl acetate was added, when a syrup was deposited. This was removed, and a further quantity of ethyl acetate added to the hot liquid. On keeping the latter for some time, a crystalline substance separated in small, hard nodules, which melted at 156°, and readily reduced Fehling’s solution (Found, C = 399; H = 69. C5H]0O5 requires C = 400; H = 67 per cent.). The optical rotatory power of the substance was determined with the following result: 0T702, made up to 25 c.c. with water, gave aD + 1°2V in a 2-dcm. tube, whence [a]D+1065°. The substance yielded an osazone, which, when crystallised from dilute alcohol, was obtained in brownish-yellow needles, melting at 160° (Found, C = 622; H = 62. C17H20O3N4 requires C = 622; H = 6T per cent.). From the above results it was evident that the sugar formed by the hydrolysis of caulophyllosaponin is a pentose, agreeing in all its properties with £-arabinose, In order further to confirm its