Elemicin 192

Elemicin (4-allyl-l,2,6-trimethoxy benzene), C12H1603, constitutes the principal constituent of Manila elemi oil, in which it was discovered by Semmler1) who also gave it its name. It is found in fraction 277 to 280° of elemi oil.2) In order to isolate elemicin, the fraction in question is boiled for half an hour with formic acid. As Semmler has demonstrated by experiments made on anethol and safrol, allyl compounds remain unchanged, whereas propenyl compounds are destroyed. Elemicin purified in this manner possessed the following properties:

B. p. 144 to 147°; d20o1,063; nD 1,52848.

When oxidized in acetone solution with potassium permanganate trimethylgallic acid, C10H12O5, m. p. 169°; b. p. 225 to 227°, results.

When heated with sodium or with alcoholic potassa, iso-elemicin, an isomer of position to asarone, results. Isoelemicin is 4-propenyl-1,2,6-trimethoxy benzene and is characterized by the following constants:

1) Berl. Berichte 41 (1908), 1768, 1918, 2183, 2556. 2) Report of Schimmel & Co. October 1896, 29; April 1907, 41; October 1908, 51.

B. p. 153 to 156° (10 mm.); d20o1,073; nD 1,54679.

Isoelemicin is characterized chemically by its dibromide, m. p. 88 to 89°. Like elemicin, it yields trimethylgallic acid upon oxidation with permanganate.