Elemicin (EM)

Elemicin is a phenylpropene, a natural organic compound, and is a constituent of the essential oils of the spices nutmeg and mace. Elemicin is also a constituent of the oleoresin and essential oil of Canarium luzonicum (also referred to as elemi). Elemicin is named after this tree. Elemicin was first isolated from elemi oil using fractional distillation. Raw nutmeg causes anticholinergic-like effects, which are attributed to elemicin and myristicin. Elemicin has been used to synthesize the alkaloid mescaline. Elemicin was later 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.