Safrol 189

Safrol, C10H10O2, is the principal constituent of oil of sassafras. It is also contained in appreciable amount in camphor oil from which it is obtained technologically. In addition it has been found in the oils of Asarum arifolium, A. Blumei, American wormseed oil, Japanese staranise oil, in the common staranise oil (traces), in the oils of apopin, ylang-ylang (?), nutmeg, cinnamon leaves, cinnamon root, in the oil from the bark of Cinnamomum Mer-cadoi, in pichurimbean oil (?), in California laurel oil, and in massoy bark oil. Safrol is the methylene ether of m-allylpyrocatechin. It is a colorless or slightly yellowish, optically inactive liquid, which upon cooling congeals to a crystalline mass, and possesses the following additional properties:

1) Ciamician and Silber, Berl. Berichte 23 (1890), 1165. 2) Eykman, Bed. Berichte 23 (1890), 862.

Congealing point about + 11°; b. p. 91° (4 mm.), 233° (759mm.); d15o 1,105 to 1,107; nD20o1,536 to 1,54a1)

Eykman2) found: M. p. +8°; b. p. 229 to 231° (uncorr.); d15o1,0960; d12o1,110; nD 1,5420.

Subjected to careful oxidation with potassium permanganate, it yields first of all a glycol (m. p. 82 to 83°), which upon further oxidation yields a-homopiperonylic acid. C6H3(OOCH2)CH2COOH (m. p. 127 to 128°). When oxidized with chromic acid mixture, piperonal (heliotropin), m. p. 37°, and piperonylic acid, C6H3(OOCH2)COOH (m. p. 228°) result.

When reduced in alcoholic solution with sodium, or with nickel in a current of hydrogen, safrol as well as Isosafrol yield the dihydro-derivative C10H12O2 (b. p. 228°) and /77-propylphenol (b. p. 228°).3)