Routes of
administration Oral PubChem CID 10248 KEGG C10451 | CAS Number 487-11-6 ChemSpider 9830 Molar mass 208.25 g/mol | |
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Legal status In general: uncontrolled | ||
Elemicin is a phenylpropene, a natural organic compound, and is a constituent of several plant species' essential oils.
Contents
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%.
Uses
Elemicin has been used to synthesize the alkaloid mescaline.
Pharmacology
Raw nutmeg causes anticholinergic-like effects, which are attributed to elemicin and myristicin.