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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:14:42 UTC
Update Date2022-03-07 02:57:04 UTC
HMDB IDHMDB0041553
Secondary Accession Numbers
  • HMDB41553
Metabolite Identification
Common NameMethylisoeugenol
DescriptionMethylisoeugenol 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. Methylisoeugenol is a mild, bitter, and clove tasting compound. Methylisoeugenol is found, on average, in the highest concentration within a few different foods, such as nutmegs (Myristica fragrans), star anises (Illicium verum), and gingers (Zingiber officinale). Methylisoeugenol has also been detected, but not quantified in, several different foods, such as carrots (Daucus carota ssp. sativus), evergreen blackberries (Rubus laciniatus), blackberries (Rubus), tarragons (Artemisia dracunculus), and sweet basils (Ocimum basilicum). This could make methylisoeugenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Methylisoeugenol.
Structure
Data?1563863676
Synonyms
ValueSource
(Z)-Methyl isoeugenolChEBI
cis-4-Propenyl veratroleChEBI
cis-Methyl isoeugenolChEBI
(e)-Methyl eugenolHMDB
(e)-Methyl isoeugenolHMDB
1,2-Dimethoxy-4-(1-propenyl)benzene, 9ciHMDB
1,2-Dimethoxy-4-propenyl-(e)-benzeneHMDB
1,2-Dimethoxy-4-propenyl-benzeneHMDB
1,2-Dimethoxy-4-propenylbenzeneHMDB
1,3,4-Isoeugenol methyl etherHMDB
1-(3,4-Dimethoxyphenyl)-1-propeneHMDB
1-Veratryl-1-propeneHMDB
3,4-DimethoxypropenylbenzeneHMDB
4-(1-Propenyl)veratroleHMDB
4-Propenyl-1,2-dimethoxybenzeneHMDB
4-PropenylveratroleHMDB
4-trans-PropenylveratroleHMDB
FEMA 2476HMDB
Isoeugenol methyl etherHMDB
Isoeugenyl methyl etherHMDB
IsohomogenolHMDB
IsomethyleugenolHMDB, MeSH
Methyl isoeugenolHMDB, MeSH
O-MethylisoeugenolHMDB
trans-4-PropenylveratroleHMDB
trans-IsomethyleugenolHMDB, MeSH
trans-Methyl isoeugenolHMDB
1,2-Dimethoxy-4-(1-e-propenyl)benzeneMeSH, HMDB
1,2-Dimethoxy-4-(1-propenyl)benzeneMeSH, HMDB
1,2-Dimethoxy-4-(1-Z-propenyl)benzeneMeSH, HMDB
Isomethyleugenol, (e)-isomerMeSH, HMDB
Isomethyleugenol, (Z)-isomerMeSH, HMDB
MethylisoeugenolMeSH
Chemical FormulaC11H14O2
Average Molecular Weight178.2277
Monoisotopic Molecular Weight178.099379692
IUPAC Name1,2-dimethoxy-4-[(1Z)-prop-1-en-1-yl]benzene
Traditional Name(Z)-methyl isoeugenol
CAS Registry Number6379-72-2
SMILES
COC1=C(OC)C=C(\C=C/C)C=C1
InChI Identifier
InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4-
InChI KeyNNWHUJCUHAELCL-PLNGDYQASA-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
  • Styrene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point16 - 17 °CNot Available
Boiling Point270.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility144.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.050 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP3.47ALOGPS
logP2.78ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.34 m³·mol⁻¹ChemAxon
Polarizability19.92 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]+144.25631661259
DarkChem[M-H]-140.49731661259
DeepCCS[M+H]+144.23430932474
DeepCCS[M-H]-141.47430932474
DeepCCS[M-2H]-177.25930932474
DeepCCS[M+Na]+152.76730932474
AllCCS[M+H]+137.932859911
AllCCS[M+H-H2O]+133.532859911
AllCCS[M+NH4]+142.032859911
AllCCS[M+Na]+143.132859911
AllCCS[M-H]-140.232859911
AllCCS[M+Na-2H]-141.132859911
AllCCS[M+HCOO]-142.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethylisoeugenolCOC1=C(OC)C=C(\C=C/C)C=C12193.0Standard polar33892256
MethylisoeugenolCOC1=C(OC)C=C(\C=C/C)C=C11433.1Standard non polar33892256
MethylisoeugenolCOC1=C(OC)C=C(\C=C/C)C=C11489.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methylisoeugenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fs-1900000000-3d41a0d29a7363963fbb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylisoeugenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 10V, Positive-QTOFsplash10-004i-0900000000-1b4a5c893c8cb3d527972016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 20V, Positive-QTOFsplash10-004i-2900000000-dd43f9e1c8e86b7ba6ff2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 40V, Positive-QTOFsplash10-0006-9500000000-20fd1ba2b53cc59be2ea2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 10V, Negative-QTOFsplash10-004i-0900000000-13d0af68ffab1cb5c56d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 20V, Negative-QTOFsplash10-004i-0900000000-02afbb666cbaaa0c075e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 40V, Negative-QTOFsplash10-07cr-4900000000-6a705aba56bdf50c37282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 10V, Positive-QTOFsplash10-004i-0900000000-cde372377d8e900ad3a32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 20V, Positive-QTOFsplash10-0fb9-0900000000-28cc89aae8d7b76189de2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 40V, Positive-QTOFsplash10-004i-9400000000-219c0ddce8933e6a09c32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 10V, Negative-QTOFsplash10-004i-0900000000-583273c8100f9e55b4bd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 20V, Negative-QTOFsplash10-004j-0900000000-75e41d1bbbb423dac95f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylisoeugenol 40V, Negative-QTOFsplash10-02u9-9800000000-aa3ed6a53e37b0107f0e2021-09-22Wishart LabView Spectrum
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 IDFDB021536
KNApSAcK IDC00050779
Chemspider ID21242881
KEGG Compound IDC10478
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl isoeugenol
METLIN IDNot Available
PubChem Compound1549045
PDB IDNot Available
ChEBI ID50550
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1435081
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cartus AT, Merz KH, Schrenk D: Metabolism of methylisoeugenol in liver microsomes of human, rat, and bovine origin. Drug Metab Dispos. 2011 Sep;39(9):1727-33. doi: 10.1124/dmd.111.038851. Epub 2011 Jun 1. [PubMed:21632962 ]
  2. Pande C, Tewari G, Singh C, Singh S, Padalia RC: Chemical composition of the essential oil of Feronia elephantum Correa. Nat Prod Res. 2010 Nov;24(19):1807-10. doi: 10.1080/14786411003752078. [PubMed:21104525 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .