Methyleugenol 186

Eugenol is frequently accompanied by its methyl ether, the methyleugenol (allylveratrol), C11h14O2. It occurs in citronella oil, Japanese calamus oil, matico oil (?), betel oil, Canada snake-root oil, in the oils of Asarum europseum (?), champaca flowers (?), paracoto bark, in the oil from the bark of Cinnamomum peda-tinervium, in culilawan oil, laurel oil, in California laurel oil, in the oil of cassie buds, and in the oils of Evodia simplex, bay, and pimenta.

Its odor reminds of that of eugenol, but is fainter. It boils at 248 to 249° (128 to 129° at 11 mm.);3) d11. 1,041; and nDl,5373.4)

In the laboratory of Schimmel & Co., the following constants were observed in connection with technical products: d15o1,04 to 1,043; n20o1,534 to 1,540; soluble in 4 vols, of 60 p. c. and in 1 to 2 vols. of 70 p. c. alcohol.

1) Journ. f. prakt. Chem. II. 56 (1897), 147.

2) Report of Schimmel & Co. Oct. 1903, 30, footnote.

3) Bertram and Gildemeister, Journ. f. prakt. Chem. II. 39 (1889), 354.

4) Eykman, Berl. Berichte 23 (1890), 862.

When boiled with alcoholic potassa, methylisoeugenol results. Bromine is added with the formation of the handsome crystalline tribrommethyleugenol, C6H2Br.(OCH3)2 'C3H5Br2, which melts at 78o 1 ) Upon oxidation with potassium permanganate it is converted into dimethoxybenzoic acid (veratric acid) which melts at 179 to 180°.-) This same acid is likewise obtained upon the oxidation of methylisoeugenol. Both compounds, as also the methyleugenol nitrite,8) m. p. 125°, can be utilized for the identification of methyleugenol.