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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:46:02 UTC
Update Date2022-03-07 02:53:09 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. 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. 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
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 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

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.5 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker133.68130932474
[M+H]+Baker138.94330932474
[M-H]-Not Available133.681http://allccs.zhulab.cn/database/detail?ID=AllCCS00001922
[M+H]+Not Available138.943http://allccs.zhulab.cn/database/detail?ID=AllCCS00001922
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.99931661259
DarkChem[M-H]-139.08131661259
DeepCCS[M+H]+141.47430932474
DeepCCS[M-H]-137.9830932474
DeepCCS[M-2H]-175.2130932474
DeepCCS[M+Na]+150.74830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethyleugenolCOC1=C(OC)C=C(CC=C)C=C12025.8Standard polar33892256
MethyleugenolCOC1=C(OC)C=C(CC=C)C=C11362.0Standard non polar33892256
MethyleugenolCOC1=C(OC)C=C(CC=C)C=C11399.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyleugenol EI-B (Non-derivatized)splash10-004i-6900000000-24e258249ebb81a10db82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyleugenol EI-B (Non-derivatized)splash10-001i-6900000000-7eab85ab8f89486d0c672017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyleugenol EI-B (Non-derivatized)splash10-004i-6900000000-511a7254b57b1693d1252017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyleugenol EI-B (Non-derivatized)splash10-004i-6900000000-6e7986f7be4dcc512bf52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyleugenol EI-B (Non-derivatized)splash10-001l-6900000000-0b489e050538331d30902017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyleugenol EI-B (Non-derivatized)splash10-004i-6900000000-24e258249ebb81a10db82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyleugenol EI-B (Non-derivatized)splash10-001i-6900000000-7eab85ab8f89486d0c672018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyleugenol EI-B (Non-derivatized)splash10-004i-6900000000-511a7254b57b1693d1252018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyleugenol EI-B (Non-derivatized)splash10-004i-6900000000-6e7986f7be4dcc512bf52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyleugenol EI-B (Non-derivatized)splash10-001l-6900000000-0b489e050538331d30902018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyleugenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g0-1900000000-ef346d457b34fcee14be2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyleugenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyleugenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-3900000000-6a0a17f77c5384cea66f2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyleugenol LC-ESI-qTof , Positive-QTOFsplash10-0006-0900000000-d41423501ff6a0caec1e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyleugenol , positive-QTOFsplash10-006t-1910000000-c6bd5f4739dc2d3b4f992017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 10V, Positive-QTOFsplash10-004i-0900000000-5bcc530b76def442eca82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 20V, Positive-QTOFsplash10-004i-1900000000-7363ea03a8cd36e7f50a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 40V, Positive-QTOFsplash10-0f6x-9600000000-8efff378856493d57d482016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 10V, Negative-QTOFsplash10-004i-0900000000-248b8d584ce0c311ffc02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 20V, Negative-QTOFsplash10-004i-0900000000-8e61ac867ff1e4b6bdd82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 40V, Negative-QTOFsplash10-07cr-4900000000-e8817397f71772abc1752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 10V, Negative-QTOFsplash10-004i-0900000000-583273c8100f9e55b4bd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 20V, Negative-QTOFsplash10-004j-0900000000-2884ce971c57cbd816d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 40V, Negative-QTOFsplash10-02u9-9800000000-4811899c7b2ebb02f8362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 10V, Positive-QTOFsplash10-004i-0900000000-98bc20876c03ad8e0e922021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 20V, Positive-QTOFsplash10-0ufr-0900000000-ba7858c7a47bbfdf0ab32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyleugenol 40V, Positive-QTOFsplash10-004i-9400000000-86967ab180df17622b532021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
MarkerDB IDNot Available
Good Scents 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.. .