Elemicin

Description

Elemicin is a trioxygenated phenylpropane that has been found in A. dracunculus. It is active against S. aureus, B. subtilis, and C. albicans (MICs = 600, 2,500, and 1,000 mg/L, respectively) but not E. coli, K. pneumoniae, P. aeruginosa (MICs = >8,000 mg/L for all), or L. monocytogenes (MIC = >3,000 mg/L). Elemicin is toxic to mice following metabolic activation to 1’-hydroxyelemicin by the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2. It increases plasma and hepatic triglyceride levels, decreases stearoyl-CoA desaturase 1 (Scd1) expression, and induces hepatomegaly in mice when administered at a dose of 500 mg/kg per day for three weeks.

Chemical properties

Clear Colorless Oil

The Uses of Elemicin

A constituent of the essential oil of nutmeg and is responsible for the psychoactive effects of nutmeg. Also a minor constituent of the oleoresin and essential oil of Manila elemi (Canarium luzonicum). Exhibits anticholinergic-like effects in humans.

Definition

ChEBI: Elemicin is an olefinic compound.

What are the applications of Application

Elemicin is a constituent of the essential oil of nutmeg

Synthesis

Prod. :
1) by isolation from Elemi oil (high-boiling fractions).
2) from Dimcthylpyrogallol plus Allyl bromide, via 2,6-Dimethyl pyrogallol allylether. This is heated in a Claisen-rearrangement reaction to yield 4-Hydroxy-3,5-dimethoxy allylbenzene. The latter is methylated to yield Elemicine.
3) From Eugenol via 5-Hydroxyeugenol.