The constitution of chaulmoogric and hydnocarpic acids / by Marmaduke Barrowcliff and Frederick B. Power.

  • Barrowcliff, Marmaduke.
Date:
[1907]
Catalogue details

Licence: In copyright

Credit: The constitution of chaulmoogric and hydnocarpic acids / by Marmaduke Barrowcliff and Frederick B. Power. Source: Wellcome Collection.

    3/26
    LVII. — The Constitution of Chaulmoogric and Hydno car pic Acids. By Marmaduke Barrowcliff and Frederick Belding Power. In a previous communication on “ The Constituents of Chaulmoogra Seeds” (Power and Gornall, Trans.. 1904, 85, 838) the isolation of a new, unsaturated, optically active acid was described. This acid, designated chaulmoogric acid, melted at 68°, had [a]D +56°, and was shown to possess the formula C18H3202. Although isomeric with linolic acid, it combined with only two atomic proportions of bromine or iodine, and must, therefore, contain in its structure both a closed ring and an ethylenic linking. In a subsequent communication, entitled “ The Constitution of Chaul¬ moogric Acid, Part I ” (Trans., 1904, 85, 851), several derivatives of this new acid were described. It was also shown that, for an unsatu¬ rated compound, it exhibited certain remarkable properties, since it was unattacked by fused alkalis, even at 300°, and when boiled with sodium and amyl alcohol the ethylenic linking was not reduced. When oxidised in alkaline solution with potassium permanganate, dihydroxydihydrochaulmoogric acid, C18H3202(0H)2, was obtained, together with formic acid, and an acid possessing the formula <J,,H280(C02H)2* The authors have extended the study of chaulmoogric acid, more especi¬ ally with regard to the products furnished by its oxidation with potassium permanganate. The present communication embodies the results obtained, and the conclusions which may be drawn from them respecting the constitution of this acid. * An ester, to which the formula Ci5H28(C02Et)2 was previously ascribed, has now been found to have consisted of impure ethyl dodecanedicar boxy late. No acid of the formula C18H2a(COaH)a is produced by the oxidation of chaulmoogric acid.