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Methylisoeugenol (FDB021536)

Record Information
Version1.0
Creation date2010-04-08 22:15:46 UTC
Update date2019-11-26 03:20:31 UTC
Primary IDFDB021536
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 wild carrots (Daucus carota), carrots (Daucus carota ssp. sativus), sweet basils (Ocimum basilicum), tarragons (Artemisia dracunculus), and evergreen blackberries (Rubus laciniatus). 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.
CAS Number6379-72-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(Z)-Methyl isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03fs-1900000000-3d41a0d29a7363963fbbSpectrum
Predicted GC-MS(Z)-Methyl isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-1b4a5c893c8cb3d527972016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-dd43f9e1c8e86b7ba6ff2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9500000000-20fd1ba2b53cc59be2ea2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-13d0af68ffab1cb5c56d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-02afbb666cbaaa0c075e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07cr-4900000000-6a705aba56bdf50c37282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-cde372377d8e900ad3a32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0900000000-28cc89aae8d7b76189de2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9400000000-219c0ddce8933e6a09c32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-583273c8100f9e55b4bd2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-0900000000-75e41d1bbbb423dac95f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02u9-9800000000-aa3ed6a53e37b0107f0e2021-09-22View Spectrum
NMRNot Available
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.