Elemicin

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Elemicin
Skeletal formula of elemicin
Ball-and-stick model of the elemicin molecule
Clinical data
Routes of
administration
Oral
Legal status
Legal status
  • In general: uncontrolled
Identifiers
CAS Number
PubChem CID
ChemSpider
KEGG
ChEMBL
ECHA InfoCard100.006.954 Edit this at Wikidata
Chemical and physical data
FormulaC12H16O3
Molar mass208.25 g/mol
3D model (JSmol)
  (verify)

Elemicin is a phenylpropene, a natural organic compound, and is a constituent of several plant species' essential oils.[1][2]

Natural occurrence[edit]

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.[1] Elemicin is also present in the oils of the spices nutmeg and mace, with it composing 2.4% and 10.5% of those oils respectively.[2]

Isolation[edit]

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[edit]

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[edit]

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

Pharmacology[edit]

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

See also[edit]

References[edit]

  1. ^ a b 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)|format= requires |url= (help). 8: 35–37. doi:10.1002/ffj.2730080107.
  2. ^ a b 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 978-0470010402.
  8. ^ Adams, Rodger (1944). "The Claisen Rearrangement". Organic Reactions, Volume II (PDF). Newyork: John Wiley & Sons, Inc. pp. 2–44 [44]. doi:10.1002/0471264180.or002.01. ISBN 978-0471264187.
  9. ^ Hahn, Georg; 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.