Showing Compound Card for O-Methyleugenol (CDB000223)

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Record Information
Version1.0
Created at2020-03-19 00:25:22 UTC
Updated at2020-12-07 19:07:16 UTC
CannabisDB IDCDB000223
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameO-Methyleugenol
DescriptionMethyleugenol, also known as 4-allylveratrole, belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying two methoxy groups. Methyleugenol is a sweet, anise, and apricot tasting compound. Outside of the human body, Methyleugenol is found 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 soybeans, evergreen blackberries, muskmelons, citrus, and pomes. 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. 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 formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Methyl eugenol is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. It is the methyl ether of eugenol and it is important in the plant-insect interaction 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 has been identified 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. Methyleugenol has also been identified in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight178.23
Monoisotopic Molecular Weight178.0994
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

Indirect biological role:

Industrial application:

Physical Properties
StateSolid
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-3900000000-6a0a17f77c5384cea66f2014-09-20View Spectrum
GC-MSO-Methyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-24e258249ebb81a10db8Spectrum
GC-MSO-Methyleugenol, non-derivatized, GC-MS Spectrumsplash10-001i-6900000000-7eab85ab8f89486d0c67Spectrum
GC-MSO-Methyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-511a7254b57b1693d125Spectrum
GC-MSO-Methyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-6e7986f7be4dcc512bf5Spectrum
GC-MSO-Methyleugenol, non-derivatized, GC-MS Spectrumsplash10-001l-6900000000-0b489e050538331d3090Spectrum
GC-MSO-Methyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-24e258249ebb81a10db8Spectrum
GC-MSO-Methyleugenol, non-derivatized, GC-MS Spectrumsplash10-001i-6900000000-7eab85ab8f89486d0c67Spectrum
GC-MSO-Methyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-511a7254b57b1693d125Spectrum
GC-MSO-Methyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-6e7986f7be4dcc512bf5Spectrum
GC-MSO-Methyleugenol, non-derivatized, GC-MS Spectrumsplash10-001l-6900000000-0b489e050538331d3090Spectrum
Predicted GC-MSO-Methyleugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03g0-1900000000-ef346d457b34fcee14beSpectrum
Predicted GC-MSO-Methyleugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSO-Methyleugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-0900000000-d41423501ff6a0caec1e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-006t-1910000000-c6bd5f4739dc2d3b4f992017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-5bcc530b76def442eca82016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-7363ea03a8cd36e7f50a2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9600000000-8efff378856493d57d482016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-248b8d584ce0c311ffc02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-8e61ac867ff1e4b6bdd82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07cr-4900000000-e8817397f71772abc1752016-08-03View 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-0900000000-2884ce971c57cbd816d52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02u9-9800000000-4811899c7b2ebb02f8362021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-98bc20876c03ad8e0e922021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-0900000000-ba7858c7a47bbfdf0ab32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9400000000-86967ab180df17622b532021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0031864
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]