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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-05-18 14:35:48 UTC
Update Date2020-02-26 21:39:04 UTC
HMDB IDHMDB0013744
Secondary Accession Numbers
  • HMDB13744
Metabolite Identification
Common Name2-Methoxy-4-vinylphenol
Description2-Methoxy-4-vinylphenol, also known as 4-vinylguaiacol or 4-ethenyl-2-methoxyphenol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 2-Methoxy-4-vinylphenol is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methoxy-4-vinylphenol is an aromatic substance used as a flavoring agent. 2-Methoxy-4-vinylphenol is a clove, curry, and peanut tasting compound. Outside of the human body, 2-Methoxy-4-vinylphenol is found, on average, in the highest concentration within a few different foods, such as wild carrots, carrots, and coffee and in a lower concentration in beers, kohlrabis, and sesames. 2-Methoxy-4-vinylphenol has also been detected, but not quantified in, several different foods, such as asparagus, evergreen blackberries, broccoli, spearmints, and cauliflowers. This could make 2-methoxy-4-vinylphenol a potential biomarker for the consumption of these foods.
Structure
Data?1582753144
Synonyms
ValueSource
2-(4-Hydroxy-3-methoxyphenyl)etheneChEBI
2m4VPChEBI
4-Ethenyl-2-methoxyphenolChEBI
4-Hydroxy-3-methoxyphenyletheneChEBI
4-Hydroxy-3-methoxystyreneChEBI
4-Hydroxy-3-methoxyvinylbenzeneChEBI
4-Vinyl-2-methoxyphenolChEBI
4-VinylguaiacolChEBI
O-Methoxy-p-vinylphenolChEBI
p-VinylguaiacolChEBI
Para-vinylguaiacolChEBI
2-Methoxy-4-vinyl-phenolHMDB
2-Methoxy-4-vinylphenol (4-vinylguaiacol)HMDB
2-Methoxy-4-vinylphenol (vinylguaiacol)HMDB
2-Methoxy-vinylphenolHMDB
2-Metoxy-4-vinyl-phenolHMDB
4-Ethenyl-2-methoxy-phenolHMDB
4-EthenylguaiacolHMDB
4-Vinyl-2-methoxyphenol ( p-vinylguaiacol)HMDB
4-Vinyl-2-methoxyphenol (4-vinylguaiacol)HMDB
4-Vinyl-O-guaiacolHMDB
4-VinylguaiacoleHMDB
Guaiacol, 4-vinylHMDB
p-Vinyl guaicolHMDB
Phenol, 2-methoxy-4-ethenylHMDB
Phenol, 4-vinyl, 2-methoxyHMDB
VinylguaiacolHMDB
Vinylguaiacol (4-vinyl-2-methoxyphenol)HMDB
VinylguajacolHMDB
Chemical FormulaC9H10O2
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
IUPAC Name4-ethenyl-2-methoxyphenol
Traditional Name2-methoxy-4-vinyl-phenol
CAS Registry Number7786-61-0
SMILES
COC1=CC(C=C)=CC=C1O
InChI Identifier
InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3
InChI KeyYOMSJEATGXXYPX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.42 g/LALOGPS
logP1.84ALOGPS
logP2.25ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.03ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.19 m³·mol⁻¹ChemAxon
Polarizability15.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udr-6900000000-c95e8007869a915d6fe6Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udr-6900000000-c95e8007869a915d6fe6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uki-2900000000-6a52b2fb0cd2b1888cbaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-8970000000-109c9889992939114454Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-9de02cce24e40d1314afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-04be6d79c3fa5851d78dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9300000000-bab367ece5e140a11583Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-cd337f7259f32e912e8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-5cef2e884a5445e8509bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-7900000000-27870d0d63eeb1b6290dSpectrum
MSMass Spectrum (Electron Ionization)splash10-0ug0-9700000000-32bccf98e351d8308924Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothNormal
    • Zhang, S., Liu, L...
details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDsNone
DrugBank IDDB03514
Phenol Explorer Compound ID632
FooDB IDFDB000857
KNApSAcK IDC00029546
Chemspider ID325
KEGG Compound IDC17883
BioCyc IDCPD-1072
BiGG IDNot Available
Wikipedia Link2-Methoxy-4-vinylphenol
METLIN IDNot Available
PubChem Compound332
PDB IDNot Available
ChEBI ID42438
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wagenstaller M, Buettner A: Quantitative determination of common urinary odorants and their glucuronide conjugates in human urine. Metabolites. 2013 Aug 7;3(3):637-57. doi: 10.3390/metabo3030637. [PubMed:24958143 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-Methoxy-4-vinylphenol → 6-(4-ethenyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
2-Methoxy-4-vinylphenol → (4-ethenyl-2-methoxyphenyl)oxidanesulfonic aciddetails