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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:32:24 UTC
Update Date2019-07-23 06:14:18 UTC
HMDB IDHMDB0033778
Secondary Accession Numbers
  • HMDB33778
Metabolite Identification
Common NameElemicin
DescriptionElemicin, also known as 5'-metoxy eugenol, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Elemicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Elemicin is a flower and spice tasting compound. Outside of the human body, elemicin is found, on average, in the highest concentration in a few different foods, such as wild carrots, carrots, and nutmegs and in a lower concentration in parsley. elemicin has also been detected, but not quantified in, several different foods, such as dills, herbs and spices, sweet bay, and tarragons. This could make elemicin a potential biomarker for the consumption of these foods. This is due to syringol's allyl aromatic ether being blocked by ethers in both ortho-positions. Elemicin is named after this tree. Elemicin has been synthesized from syringol and allyl bromide using Williamson ether synthesis and Claisen rearrangement. 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. Raw nutmeg causes anticholinergic-like effects, which are attributed to elemicin and myristicin. Elemicin is a constituent of the oleoresin and the essential oil of Canarium luzonicum (also referred to as elemi). Specifically, the substance was collected between 162-165 °C at a reduced pressure of 10 torr.
Structure
Data?1563862458
Synonyms
ValueSource
5'-Metoxy eugenolHMDB
1,2,3-Trimethoxy-5-(2-propenyl)-benzeneHMDB
1,2,3-Trimethoxy-5-(2-propenyl)benzene, 9ciHMDB
1,2,3-Trimethoxy-5-allylbenzene (elemicin)HMDB
1,2,3-Trimethoxy-5-[2-propenyl]-benzeneHMDB
3,4, 5-TrimethoxyallylbenzeneHMDB
3,4,5-TrimethoxyallylbenzeneHMDB
4-Allyl-1,2,6-trimethoxybenzeneHMDB
5-Allyl-1,2,3-trimethoxy-benzeneHMDB
5-Allyl-1,2,3-trimethoxybenzeneHMDB
Benzene, 1,2,3-trimethoxy-5-(2-propenyl)- (9ci)HMDB
Benzene, 5-(2-propenyl)-1,2,3-trimethoxyHMDB
ElemicineHMDB
Chemical FormulaC12H16O3
Average Molecular Weight208.2536
Monoisotopic Molecular Weight208.109944378
IUPAC Name1,2,3-trimethoxy-5-(prop-2-en-1-yl)benzene
Traditional Nameelemicin
CAS Registry Number487-11-6
SMILES
COC1=CC(CC=C)=CC(OC)=C1OC
InChI Identifier
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
InChI KeyBPLQKQKXWHCZSS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP3.03ALOGPS
logP2.6ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity59.73 m³·mol⁻¹ChemAxon
Polarizability22.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-1910000000-90f58b5ac3c420a0beadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-0d12e8d4c75330b0079dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3790000000-c789d6a44beb86af1b56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5900000000-f5bd2ff33bc271ebe936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-445d52139886db9fa3a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0890000000-b4607d26dffb40f5f337Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0cdr-3900000000-9daed5f20cf190665c47Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-4950000000-139934290bd7ee24b6baSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011932
KNApSAcK IDC00002739
Chemspider ID9830
KEGG Compound IDC10451
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkElemicin
METLIN IDNot Available
PubChem Compound10248
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .