Elemicin

Elemicin

Elemicin
Skeletal formula of elemicin
Ball-and-stick model of the elemicin molecule
Systematic (IUPAC) name
1,2,3-Trimethoxy-5-prop-2-enylbenzene
Clinical data
Legal status
  • Uncontrolled
Routes of
administration
Oral
Identifiers
CAS Registry Number  Y
PubChem CID:
ChemSpider  Y
KEGG  Y
ChEMBL  Y
Chemical data
Formula C12H16O3
Molecular mass 208.25 g/mol
 Y   

Elemicin is a essential oils.[1][2]


Contents

  • Natural Occurrence 1
  • Isolation 2
  • Preparation 3
  • Uses 4
  • Pharmacology 5
  • See also 6
  • References 7

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

References

  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) 8: 35–37.  
  2. ^ a b Leela, N. (2008). Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. pp. 165–188 [170].  
  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.  
  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.  
  5. ^ F. Mauthner (1918). "Die Synthese des Elemicins und Isoelemicins". Justus Liebigs Annalen der Chemie 414 (2): 250–255.  
  6. ^ Editor (1918). "Synthesis of Elemicin and of isoElemicin". Journal of the Chemical Society, Abstracts 114: i428.  
  7. ^ Thomas, Laue (2005). Named Organic Reactions, 2nd Edition. Wolfsburg, Germany: John Wiley & Sons, Ltd. pp. 58–60 [59].  
  8. ^ Adams, Rodger (1944). Organic Reactions, Volume II (PDF). Newyork: John Wiley & Sons, Inc. pp. 2–44 [44].  
  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.  
  10. ^ McKenna, A.; Nordt, S. P.; Ryan, J. (2004). "Acute Nutmeg Poisoning". European Journal of Emergency Medicine 11 (4): 240–241.  
  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.