Elemicin

Elemicin

Clinical data
Routes of administration	Oral
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 1,2,3-Trimethoxy-5-(prop-2-en-1-yl)benzene
CAS Number	487-11-6 Y
PubChem CID	10248
ChemSpider	9830 Y
KEGG	C10451 Y
ChEMBL	CHEMBL458690 Y
ECHA InfoCard	100.006.954
Chemical and physical data
Formula	C12H16O3
Molar mass	208.25 g/mol
3D model (Jmol)	Interactive image
SMILES C=CCC1=CC(OC)=C(OC)C(OC)=C1
InChI InChI=1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3 Y Key:BPLQKQKXWHCZSS-UHFFFAOYSA-N Y

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

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.

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.

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%.

Elemicin has been used to synthesize the alkaloid mescaline.

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