Survey with prize
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:46:02 UTC
Update Date2019-07-23 06:09:42 UTC
HMDB IDHMDB0031864
Secondary Accession Numbers
  • HMDB31864
Metabolite Identification
Common NameMethyleugenol
DescriptionMethyleugenol, also known as 4-allylveratrole or eugenol methyl, 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. Methyleugenol is an extremely weak basic (essentially neutral) compound (based on its pKa). FDA noted the action was despite its continuing stance that this substance does not pose a risk to public health under the conditions of its intended use. Methyleugenol is a sweet, anise, and apricot tasting compound. Outside of the human body, Methyleugenol is found, on average, in the highest concentration within a few different foods, such as allspices, tarragons, and sweet bay and in a lower concentration in sweet basils, rosemaries, and hyssops. Methyleugenol has also been detected, but not quantified in, several different foods, such as soy beans, evergreen blackberries, muskmelons, citrus, and pomes. This could make methyleugenol a potential biomarker for the consumption of these foods. As of October 2018, the US FDA withdrew authorization for the use of methyl eugenol as a synthetic flavoring substance for use in food because petitioners provided data demonstrating that these additives induce cancer in laboratory animals. Methyleugenol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Methyl eugenol (allylveratrol) is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. It is the methyl ether of eugenol and is important to insect behavior and pollination. Their ability to attract insects, particularly Bactrocera fruit flies was first noticed in 1915 by F. M. Howlett. The compound may have evolved in response to pathogens, as methyl eugenol has some antifungal activity. Methyl eugenol is found in a number of plants (over 450 species from 80 families including both angiosperm and gymnosperm families) and has a role in attracting pollinators. About 350 plant species have them as a component of floral fragrance.
Structure
Data?1563862182
Synonyms
ValueSource
1,2-Dimethoxy-4-(2-propenyl)benzeneChEBI
Eugenol methyl etherChEBI
Methyl eugenolChEBI
O-MethyleugenolKegg
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
MethyleugenolChEBI
4-Allyl-1,2-dimethoxybenzeneMeSH
1-Allyl-3,4-dimethoxybenzeneMeSH
Chemical FormulaC11H14O2
Average Molecular Weight178.2277
Monoisotopic Molecular Weight178.099379692
IUPAC Name1,2-dimethoxy-4-(prop-2-en-1-yl)benzene
Traditional Namemethyl eugenol
CAS Registry Number93-15-2
SMILES
COC1=C(OC)C=C(CC=C)C=C1
InChI Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.5 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-6900000000-24e258249ebb81a10db8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-6900000000-7eab85ab8f89486d0c67Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-6900000000-511a7254b57b1693d125Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-6900000000-6e7986f7be4dcc512bf5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001l-6900000000-0b489e050538331d3090Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-6900000000-24e258249ebb81a10db8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-6900000000-7eab85ab8f89486d0c67Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-6900000000-511a7254b57b1693d125Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-6900000000-6e7986f7be4dcc512bf5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001l-6900000000-0b489e050538331d3090Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g0-1900000000-ef346d457b34fcee14beSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-0900000000-d41423501ff6a0caec1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-006t-1910000000-c6bd5f4739dc2d3b4f99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-5bcc530b76def442eca8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-7363ea03a8cd36e7f50aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9600000000-8efff378856493d57d48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-248b8d584ce0c311ffc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-8e61ac867ff1e4b6bdd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07cr-4900000000-e8817397f71772abc175Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-3900000000-6a0a17f77c5384cea66fSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDFDB008548
KNApSAcK IDC00002741
Chemspider ID21106140
KEGG Compound IDC10454
BioCyc IDCPD-6482
BiGG IDNot Available
Wikipedia LinkMethyl eugenol
METLIN IDNot Available
PubChem Compound7127
PDB IDNot Available
ChEBI ID4918
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:17049512 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .