Elemicin


Elemicin is a phenylpropene, a natural organic compound, and is a constituent of several plant species' essential oils.

Natural occurrence

Elemicin is a constituent of the oleoresin and the essential oil of Canarium luzonicum. Elemicin is named after this tree. One study found it to compose 2.4% of the fresh essential oil. Elemicin is also present in the oils of the spices nutmeg and mace, with it composing 2.4% and 10.5% of those oils respectively. Structurally, elemcin is similar to myristicin, differing only by myristicin's methyl group that joins the two oxygen atoms that make up its dioxymethy moiety, with both constituents being found in nutmeg and mace.

Isolation

Elemicin was first isolated from elemi oil using vacuum distillation. Specifically, the substance was collected between 162-165 °C at a reduced pressure of 10 torr.

Preparation

Elemicin has been synthesized from syringol and allyl bromide using Williamson ether synthesis and Claisen rearrangement. The electrophilic aromatic substitution entering the para-position was made possible by secondary Cope rearrangement. This is due to syringol's allyl aromatic ether being blocked by ethers in both ortho-positions. When blocked the allyl group migrates to the para-position, in this case with yields above 85%.

Uses

Elemicin has been used to synthesize the proto-alkaloid mescaline.

Pharmacology

Raw nutmeg causes anticholinergic-like effects, which are attributed to elemicin and myristicin.