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.

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    sulphuric acid, no evidence was afforded of its pre-existence in the oil. Briihl (Ber., 1888, 21, 472), with consideration of the statements respecting the character of the so-called “ myristicol,” and from purely physical data, which apparently were obtained by the examina¬ tion of a fraction of nutmeg oil boiling at 224°, was led to the conclu¬ sion that, as an alcohol of the formula C10H16O, myristicol was to be regarded as a cyclic compound containing two ethylenic linkings. He, moreover, suggested constitutional formulae which w*ere believed to be in accordance with the physical determinations. Wallach (Annalen, 1889, 252, 105) examined the lower boiling portions of an oil which he designated as “mace oil,” and positively established the presence of pinene and dipentene. In this connexion, he noted that “it was remarkable that the fractions containing pinene were nearly inactive (very slightly laevorotatory). The crude oil, on the other hand, as also the fractions of higher boiling point, were strongly dextrorotatory. It is to be assumed that in the low boiling portion, + and - pinene neutralise each other. The nature of the higher boiling, dextrorotatory portions of mace oil still remains to be cleared up.” The investigation of the oils of nutmeg and mace was subsequently undertaken by Semmler (Ber., 1890, 23, 1803 ; 1891, 24, 3818). The oil of nutmeg supplied to him had a density of 0*8611 at 15°, and was found to consist entirely of terpenes, but these were not further examined. He particularly noted the absence of cymene, “ myristicol,” and higher boiling oils of high specific gravity, and stated that the oil in question evidently represented the portions which are most volatile in steam. These results led Semmler to examine an oil of mace, which was found to have a specific gravity of 0*9309 at 14°, and to give a green coloration with ferric chloride, indicating the presence of a phenolic substance. A fraction collected between 70° and 144° at 10 mm. pressure was assumed to contain “myristicol,” but was not further examined. From the higher boiling portions of the oil, after treatment vrith sodium, a crystalline substance was isolated, to which Semmler gave the name myristicin, and assigned to it the formula C12H1403. It was subsequently showm, howTever, that myristicin has the formula CnH1203, and is 3-meihoxy-4 :5-methylenedioxy-l-allyl- benzene. This substance is a liquid, but, by treatment with metallic sodium or with alkalis, it is readily converted into the correspond¬ ing propenyl compound (m. p. 45°), which has been designated isomyristicin (compare Thoms, Ber., 1903, 36, 3446; Richter, Ber. Deut. pharm. Ges., 1907, 17, 152 ; Rimini, Gazzetta, 34, ii, 281 ; 35, i, 406 ; Rimini and Olivari, Atti R. Accad. Lincei, 1907, [v], 16, i, 663).