Asarone 191

Asarone (4-propenyl-l,2,5-trimethoxybenzene), C12H1603, is a constituent of Asarum oil. It has been found in the oils of calamus, matico and Asarum arifolium. If present in larger amounts, it separates upon prolonged standing. Asarone has likewise been obtained synthetically.

In the pure state asarone is devoid of odor and taste and is further characterized by the following properties:

M. p. 61°;5) d11o 1,091; nD1,5719.6)

1) Observation made in the laboratory of Schimmel & Co.

2) Eykman, Berl. Berichte 23 (1890), 859.

3) Hoering, Berl. Berichte 38 (1905), 3466; 40 (1907), 1101.

4) Berl. Berichte 42 (1909), 3076.

5) Gattermann and Eggers, Berl. Berichte 32 (1899), 290. 6) Eykman, ibidem 23 (1890), 862.

Upon bromination it yields the well crystallizable dibromide, Cl2H10Br2O3, m. p. 86°. When treated with sodium methylate in the cold, this in turn yields the crystalline C6 H2 (OCH3)3 CH(OCH3)CHBrCH3, melts at 77,5°.

Oxidized with chromic acid, asarone yields asaryl aldehyde C10Hl2O4, m. p. 114°. Together with asaronic acid [trimethoxy-benzoic acid, C6H2(OCH8)3COOH, m. p. 144°], this is also formed when asarone is oxidized with permanganate.