The constituents of the essential oil of nutmeg / by Frederick B. Power and Arthur H. Salway.

  • Frederick Belding Power
Date:
[1907?]
Catalogue details

Licence: In copyright

Credit: The constituents of the essential oil of nutmeg / by Frederick B. Power and Arthur H. Salway. Source: Wellcome Collection.

    18/26 (page 2052)
    Since not more than a trace of substance of aldehydic or ketonic nature was present in the fraction of the oil employed, it is evident that the above-mentioned diketone must represent the oxidation pro¬ duct of an unidentified compound, which is doubtless an alcohol. The light petroleum liquid which had been separated from the dioxime, as above described, possessed a strongly camphoraceous odour. After the removal of the solvent, a brown oil was obtained which did not solidify, and was therefore distilled under diminished pressure. From the first portions of the distillate a solid separated which had the characteristic odour of camphor, and, after drying on a porous tile, melted at 170—175°. This substance readily yielded a semi- carbazone melting at 238°, and when the latter was mixed with eamphorsemicarbazone the melting point remained unchanged. Not having obtained the camphor in the form of its oxime by the treat¬ ment of the original product of oxidation with hydroxylamine, it may be assumed that the amount of the latter was only sufficient to com¬ bine with the diketone which was present in the mixture. The identification of camphor as a product of oxidation of the fraction boiling between 205° and 215° affords conclusive evidence of the presence of borneol in the original oil. Identification of Geraniol. Fraction 215—225°.—This was a comparatively large fraction. It was a colourless liquid, possessing a rose-like odour : 0-1109 gave 0-3136 C02 and 0-1055 H20. 0 = 77*1; H=10-6. This fraction was found to contain some terpineol, since it readily yielded the crystalline dipentene dihydriodide (m. p. 80°) on treatment with concentrated hydriodic acid, whilst the analytical results also indicated it to contain some of the constituents of the succeeding fraction. A portion of the fraction was oxidised with a chromic acid mixture, when the odour of citral was at first strongly developed, and from the final product a further small amount of the diketone, CsH1402, was obtained in the form of its dioxime (in. p. 140°), which has been described in connexion with the preceding fraction. As the odour of the fraction, together with the evident formation of citral by its limited oxidation, indicated the presence *of geraniol, a portion of it was treated with diphenylcarbamic chloride in the presence of pyridine, according to the method suggested by Erdmann (Jpr. Chem., 1897, [ii], 56, 8), when a product was obtained which crystallised from alcohol in thin, colourless needles melting at 81—82°. This was found to be identical with the diphenylurethane (m. p. 82°)