Methyleugenol (CHEM003832)

Record Information
Version1.0
Creation Date2014-09-11 05:20:24 UTC
Update Date2026-08-18 10:32:52 UTC
Accession NumberCHEM003832
Identification
Common NameMethyleugenol
ClassSmall Molecule
Description
Methyleugenol is found in allspice. Methyleugenol is present in many essential oils, e.g. nutmeg, mace and also many fruits, e.g. apple, banana, orange juice or peel, grapefruit, bilberry Methyleugenol has been shown to exhibit anti-nociceptive function (1). Methyleugenol belongs to the family of Anisoles. These are organic compounds contaiing a methoxybenzene or a derivative thereof.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ether
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Plant Toxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Dimethoxy-4-(2-propenyl)benzeneChEBI
Eugenol methyl etherChEBI
Methyl eugenolChEBI
O-MethyleugenolKegg
MethyleugenolChEBI
1, 2-Dimethoxy-4-(2-propenyl)benzeneHMDB
1-(3, 4-Dimethoxyphenyl)-2-propeneHMDB
4-Allyl-1, 2-dimethoxybenzeneHMDB
4-Allyl-1,2-dimethoxy-benzeneHMDB
4-Allyl-1,2-dimethyoxybenzeneHMDB
4-AllylveratroleHMDB
Allyl-1,2-dimethoxybenzeneHMDB
Benzene, 4-(2-propenyl)-1,2-dimethoxyHMDB
Eugenol methylHMDB
FEMA 2475HMDB
4-Allyl-1,2-dimethoxybenzeneMeSH
1-Allyl-3,4-dimethoxybenzeneMeSH
1,2-Dimethoxy-4-(2-propen-1-yl)benzenePhytoBank
1,2-Dimethoxy-4-allylbenzenePhytoBank
1,3,4-Eugenol methyl etherPhytoBank
1-(3,4-Dimethoxyphenyl)-2-propenePhytoBank
3,4-Dimethoxy-1-(2-propenyl)benzenePhytoBank
3,4-DimethoxyallylbenzenePhytoBank
3-(3,4-Dimethoxyphenyl)-1-propenePhytoBank
3-(3,4-Dimethoxyphenyl)propenePhytoBank
Chavibetol methyl etherPhytoBank
Eugenyl methyl etherPhytoBank
Methyl eugenol etherPhytoBank
Methyl eugenyl etherPhytoBank
MethylchavibetolPhytoBank
Veratrole methyl etherPhytoBank
Chemical FormulaC11H14O2
Average Molecular Mass178.228 g/mol
Monoisotopic Mass178.099 g/mol
CAS Registry Number93-15-2
IUPAC Name1,2-dimethoxy-4-(prop-2-en-1-yl)benzene
Traditional Namemethyl eugenol
SMILESCOC1=C(OC)C=C(CC=C)C=C1
InChI IdentifierInChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3
InChI KeyZYEMGPIYFIJGTP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
Alternative Parents
Substituents
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Phenoxy compound
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-4 °C
Boiling PointNot Available
Solubility0.5 mg/mL at 25 °C
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.99ALOGPS
logP2.76ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.27 m³·mol⁻¹ChemAxon
Polarizability19.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (2)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0031864
FooDB IDFDB008548
Phenol Explorer IDNot Available
KNApSAcK IDC00002741
BiGG IDNot Available
BioCyc IDCPD-6482
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMethyl eugenol
Chemspider ID21106140
ChEBI ID4918
PubChem Compound ID7127
Kegg Compound IDC10454
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yano S, Suzuki Y, Yuzurihara M, Kase Y, Takeda S, Watanabe S, Aburada M, Miyamoto K: Antinociceptive effect of methyleugenol on formalin-induced hyperalgesia in mice. Eur J Pharmacol. 2006 Dec 28;553(1-3):99-103. Epub 2006 Sep 23.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.