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 (also referred to as elemi). Elemicin is named after this tree. One study found it to comprise 2.4% of the fresh essential oil. Elemicin is also present in the oils of the spices nutmeg and mace, with it comprising 2.4% and 10.5% of those oils respectively.

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%.