Elemicin

Elemicin

Systematic (IUPAC) name
1,2,3-Trimethoxy-5-prop-2-enylbenzene
Clinical data
Routes of administration	Oral
Legal status	Uncontrolled
Identifiers
CAS Number	487-11-6
PubChem	CID 10248
ChemSpider	9830
KEGG	C10451
ChEMBL	CHEMBL458690
Chemical data
Formula	C12H16O3
Molar mass	208.25 g/mol
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 Key:BPLQKQKXWHCZSS-UHFFFAOYSA-N
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Elemicin is a phenylpropene, a natural organic compound, and is a constituent of several plant species' essential oils.^[1][2]

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.^[1] 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.^[2]

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.^[3][4]

Preparation

Elemicin has been synthesized from syringol and allyl bromide using Williamson ether synthesis and Claisen rearrangement.^[5][6] The electrophilic aromatic substitution entering the para-position was made possible by secondary Cope rearrangement.^[7] 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%.^[8]

Uses

Elemicin has been used to synthesize the alkaloid mescaline.^[9]

Pharmacology

Raw nutmeg causes anticholinergic-like effects, which are attributed to elemicin and myristicin.^[10][11]

See also

• Nutmeg oil
• Myristicin
• Phenylpropanoid

References

1. Villanueva, M. A.; Torres, R. C.; Baser, K. H. C.; Özek, T.; Kürkçüoglu, M. (1993). "The Composition of Manila Elemi Oil". Flavour and Fragrance Journal (pdf) 8: 35–37. doi:10.1002/ffj.2730080107.
2. Leela, N. (2008). Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. pp. 165–188 [170]. ISBN 9781845934057.
3. Editor (1908). "Constituents of Essential Oils. Elemicin, a High-boiling Constituent of Elemi Oil, and the Displacement of Alkyloxygroups in the Benzene Nucleus by Hydrogen". Journal of the Chemical Society, Abstracts 94 (A493): 557–558. doi:10.1039/CA9089400493.
4. Semmler, Friedrich (1908). "Zur Kenntnis der Bestandteile der ätherischen Öle. (Über das Elemicin, einen hochsiedenden Bestandteil des Elemiöls, und über Ersetzung von Alkyloxy-gruppen am Benzolkern durch Wasserstoff.)". Berichte der deutschen chemischen Gesellschaft 41 (2): 1768–1775. doi:10.1002/cber.19080410240.
5. F. Mauthner (1918). "Die Synthese des Elemicins und Isoelemicins". Justus Liebigs Annalen der Chemie 414 (2): 250–255. doi:10.1002/jlac.19184140213.
6. Editor (1918). "Synthesis of Elemicin and of isoElemicin". Journal of the Chemical Society, Abstracts 114: i428. doi:10.1039/CA9181400421.
7. Thomas, Laue (2005). Named Organic Reactions, 2nd Edition. Wolfsburg, Germany: John Wiley & Sons, Ltd. pp. 58–60 [59]. ISBN 0470010401.
8. Adams, Rodger (1944). Organic Reactions, Volume II (PDF). Newyork: John Wiley & Sons, Inc. pp. 2–44 [44]. doi:10.1002/0471264180.or002.01.
9. Hahn, Georg; and Wassmuth, Heinrich (1934). "Über β-[Oxyphenyl]-äthylamine und ihre Umwandlungen, I. Mitteil.: Synthese des Mezcalins". Berichte der deutschen chemischen Gesellschaft (A and B Series) 67 (4): 696–708. doi:10.1002/cber.19340670430.
10. McKenna, A.; Nordt, S. P.; Ryan, J. (2004). "Acute Nutmeg Poisoning". European Journal of Emergency Medicine 11 (4): 240–241. doi:10.1097/01.mej.0000127649.69328.a5. PMID 15249817.
11. Shulgin, A. T.; Sargent, T.; Naranjo, C. (1967). "The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines" (pdf). Psychopharmacology Bulletin 4 (3): 13. PMID 5615546.