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 compose 2.4% of the fresh essential oil. Elemicin is also present in the oils of the spices nutmeg and

mace Mace may refer to: Spices * Mace (spice), a spice derived from the aril of nutmeg * '' Achillea ageratum'', known as English mace, a flowering plant once used as a herb Weapons * Mace (bludgeon), a weapon with a heavy head on a solid shaft used ...

, with it composing 2.4% and 10.5% of those oils respectively. Structurally, elemicin is similar to

myristicin Myristicin is a naturally occurring compound found in common herbs and spices, the most well known being nutmeg. It is an insecticide, and has been shown to enhance the effectiveness of other insecticides in combination. Myristicin is also a pre ...

, 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 Mescaline or mescalin (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. Biological sou ...

Pharmacology

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

. Elemicin inhibits Stearoyl-CoA Desaturase 1 (SCD1) by metabolic activation. Elemicin is one of the main components in aromatic food and has antimicrobial, antioxidant, and antiviral activities. Elemicin possesses genotoxicity and carcinogenicity. Excess consumption of raw nutmeg results in delirium and disorientation.

References