Methylchavicol 179

Methylchavicol (estragol, isoanethol, p-allylanisol), C10H12O, was first found in anise bark oil, later also in staranise oil,

1) Berl. Berichte 23 (1890), 862.

Japanese staranise oil, kobuschi oil (?), in the oils of Persea gratissima, bay, anise, chervil, fennel, Pseudocymopterus anis-atus, in German, French and Japanese basilicum oils, in esdragon oil, and in American wood turpentine oil. It has also been obtained synthetically.

Methylchavicol is a colorless liquid with a slight anise-like odor, but which does not possess the intensively sweet taste of anethol. It is optically inactive; boils at 215 to 216° (corr.);1) d115o 0,979; nD1,5244.2) According to Schimmel & Co. the ether isolated from esdragon oil possesses the following properties:

B. p. 97 to 97,5° (12 mm.); 86° (7 mm.); d15o0,9714 to 0,972; nD16o 1,52355 to 1,52380.

Methylchavicol can be characterized by its conversion into the solid anethol by boiling it with alcoholic potassa, or by its conversion into homoanisic acid (p-methoxy phenyl acetic acid)3) which melts at 86°. In addition, however, anisic acid, m. p. 184°, which likewise results from anethol, is also formed. A confounding of the two phenol ethers, however, can be avoided by attention to the differences in the physical constants. Monobrommethyl-chavicol dibromide,4) which melts at 62,4°, can also be used for the identification of the ether.