Chemical examination of the root of ipomoea orizabensis / by Frederick B. Power and Harold Rogerson.

  • Frederick Belding Power
Date:
[1912?]
Catalogue details

Licence: In copyright

Credit: Chemical examination of the root of ipomoea orizabensis / by Frederick B. Power and Harold Rogerson. Source: Wellcome Collection.

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    Summary. The material employed for this investigation consisted of the roots of Ipomoea orizabtnsis, Ledanois (Nat. Ord. Convolvulaceae), which are commonly known as “ Mexican Scammony Root.” The root w*as found to contain 14’55 per cent, of resin, 71 per cent, of which was soluble in ether. After treatment with animal charcoal the resin was obtained nearly colourless. It then melted at 125—130°, and had [aJD — 23'0°. For a complete examination of the root, 48'76 kilograms of the ground material were extracted with hot alcohol. A portion of the concentrated extract was employed for determining the presence of sucrose, and a small amount of the latter was isolated. Another portion of the extract was distilled in a current of steam, when a very small amount of a pale yellow essential oil was obtained. From the portion of the extract which was soluble in water, the following compounds were isolated : (i) scopoletin, C10H8O4 (m. p. 203—204°), a small proportion of which appeared to be present in the form of a glucoside; (ii) 3:4-dihydroxycinnamic acid, C9H804 (m. p. 223—225°), from which the methyl ester (m. p. 158—160°) was prepared. The aqueous liquid contained, furthermore, a quantity of sugar, which yielded ei-phenylglucosazone (m. p. 205—206°). The portion of the alcoholic extract which was insoluble in water consisted of a resin which possessed the above-mentioned characters. The resin was first successively extracted with various solvents, and the resulting extracts were then further examined. I. Petrol turn Extract of the Resin.—From this extract the following substances were obtained: (i) hentriacontane, CgjH^; (ii) a phytosterol, C27H460; (iii) cetyl alcohol, C16H340; (iv) a mixture of fatty acids, consisting of palmitic, stearic, oleic, and linolenic acids. II. Ethereal Extract of the Resin.—The optical rotatory power of this extract was [a_jD — 20'5°. After hydrolysis with barium hydroxide it yielded : (i) ipuranol, C23H3S°2(OH)2 i (ii) d-a-methyl- butyric acid; (iii) tiglic acid; and a product which on acid hydro¬ lysis gave (iv) jalapinolic acid, C15H30(OH)*CO2H (m. p. 67—68°; [a]D +0'79°), together with a little methyl jalapinolate, and (v) a mixture of sugars, consisting of dextrose and a methylpentose. The latter yielded an osazone melting at 180—182°, and a tetra-acetyl derivative, CGHs05(C0,CH3)4, which apparently is a new compound. This derivative crystallises in haudsome, prismatic needles, melting at 142—143°, and has [a]Jt +21'64°. The ethyl acetate extract of the product resulting from the alkaline hydrolysis of the ethereal extract of the resin gave on oxidation with nitric acid a mixture