Chenopodium oil / by Thomas Anderson Henry and Humphrey Paget.

  • Henry, Thomas Anderson, 1873-1958
Date:
[1921.]
Catalogue details

Licence: Public Domain Mark

Credit: Chenopodium oil / by Thomas Anderson Henry and Humphrey Paget. Source: Wellcome Collection.

    11/16 (page 1722)
    The only difference observed in the course of the oxidations with permanganate in (a) water and (b) acetone was that in the former case the volatile acids produced included «<sobutyric acid (Found : in the silver salt, Ag = 55-5, 55*7. Calc., Ag = 55*39 per cent.), which was separated from the acetic acid also formed by fractional crystallisation of the anilides, acetanilide, m. p. 114°, separating first from boiling water and zsobutyranilide, m. p. 102°, last. Oxidation with permanganate of the hydrocarbon fraction of chenopodium oil from which a-terpinene had been removed (p. 1717) yielded acetic and isobutyric acids and the volatile, crystalline acid melting at 117°. The latter appears, therefore, to be the only oxidation product found which may be characteristic of the lsevoro- tatory terpene, and so far it has not been possible to obtain it in quantity sufficient for examination. From this terpinene-free fraction of the hydrocarbon mixture 58 per cent, of cymene was recovered on oxidation. Oxidation of limonene and phellandrene, under the conditions described above, yielded none of the crystalline products obtained from the chenopodium mixture of hydrocarbons, thus confirming evidence already given of the absence of these terpenes from the mixture. Ascaridole Fraction. As already stated, fraction (c) consisted almost wholly of ascaridole and on redistillation had b. p. 108—110°/15 mm., dlb° 1*0120, [a]jf —0*5°, constants which are in good agreement with those already on record (Found : C = 71*63; H = 9*45. Calc., C = 71*43; H = 9*53 per cent.). As stated above, ascaridole, when heated above 160°, is converted explosively into an isomeric substance, ascaridole glycol anhydride, the temperature rising to about 300°. Nelson found that the action could be readily con¬ trolled by dropping ascaridole into cymene heated at 150°. The authors found that dilution of ascaridole with any volatile, indifferent solvent boiling at about 130—150°, for example, xylene, will serve equally well. After the reaction is complete, the solvent is distilled off, leaving a residue of the anhydride which can be purified by distillation. It forms a viscous, yellow oil, b. p. 230—245°/755 mm., 122—125o/20 mm.; dl5° 1*026; [a]lf -0*72°. By treatment with steam, the anhydride is converted into ascaridole glycol, which is not volatile in steam, but can be distilled apparently unchanged under reduced pressure. Obtained in this way, it is a heavy, green, viscous oil, b. p. 135—160°/15 mm. (Found : C = 64*55; H = 9*74. Calc., C = 64*46; H = 9*74 per cent.). It was previously prepared by Nelson (loc. cit.) by