Record Information
Version1.0
Creation date2010-04-08 22:15:46 UTC
Update date2019-11-27 17:41:47 UTC
Primary IDFDB021536
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethylisoeugenol
DescriptionMethylisoeugenol, also known as (e)-methyl eugenol or 4-propenylveratrole, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Methylisoeugenol is a mild, bitter, and clove tasting compound. Methylisoeugenol is found, on average, in the highest concentration in a few different foods, such as nutmegs, star anises, and gingers and in a lower concentration in . Methylisoeugenol has also been detected, but not quantified in, several different foods, such as carrots, ceylon cinnamons, sweet basils, tarragons, and wild carrots. This could make methylisoeugenol a potential biomarker for the consumption of these foods.
CAS Number6379-72-2
Structure
Thumb
Synonyms
SynonymSource
(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
Methyl isoeugenolHMDB
O-MethylisoeugenolHMDB
trans-4-PropenylveratroleHMDB
trans-IsomethyleugenolHMDB
trans-Methyl isoeugenolHMDB
1,2-Dimethoxy-4-(1-e-propenyl)benzeneHMDB
1,2-Dimethoxy-4-(1-propenyl)benzeneHMDB
1,2-Dimethoxy-4-(1-Z-propenyl)benzeneHMDB
Isomethyleugenol, (e)-isomerHMDB
Isomethyleugenol, (Z)-isomerHMDB
MethylisoeugenolMeSH
(e)-methyl eugenolbiospider
(e)-methyl isoeugenolbiospider
1,2-Dimethoxy-4-(1-propenyl)benzene, 9CIdb_source
Benzene, 1,2-dimethoxy-4-propenyl-biospider
Benzene, 1,2-dimethoxy-4-propenyl-, (E)-biospider
O-methylisoeugenolbiospider
Trans-isomethyleugenolbiospider
Trans-methyl isoeugenolbiospider
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC11H14O2
IUPAC name1,2-dimethoxy-4-[(1Z)-prop-1-en-1-yl]benzene
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C(OC)C=C(\C=C/C)C=C1
Average Molecular Weight178.2277
Monoisotopic Molecular Weight178.099379692
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 74.13%; H 7.92%; O 17.95%DFC
Melting PointMp 16-17°DFC
Boiling PointBp12 138-140°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.5616DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fs-1900000000-3d41a0d29a7363963fbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-1b4a5c893c8cb3d52797View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-dd43f9e1c8e86b7ba6ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9500000000-20fd1ba2b53cc59be2eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-13d0af68ffab1cb5c56dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-02afbb666cbaaa0c075eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07cr-4900000000-6a705aba56bdf50c3728View in MoNA
ChemSpider ID21242881
ChEMBL IDCHEMBL1164609
KEGG Compound IDC10478
Pubchem Compound ID1549045
Pubchem Substance IDNot Available
ChEBI ID6877
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41553
CRC / DFC (Dictionary of Food Compounds) IDMVN84-F:NZP08-I
EAFUS ID1891
Dr. Duke IDMETHYL-ISOEUGENOL|(E)-METHYL-ISOEUGENOL|ISOEUGENOL-METHYL-ETHER|TRANS-METHYL-ISOEUGENOL
BIGG IDNot Available
KNApSAcK IDC00002760
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1435071
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anestheticDUKE
anti aggregantDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidicideDUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
insect attractant24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
toxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
clove
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.