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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-05-18 14:35:48 UTC
Update Date2018-05-19 22:57:14 UTC
HMDB IDHMDB0013744
Secondary Accession Numbers
  • HMDB13744
Metabolite Identification
Common Name2-Methoxy-4-vinylphenol
Description4-Vinylguaiacol, also known as 2m4VP or guaiacol, 4-vinyl, 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. 4-Vinylguaiacol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4-Vinylguaiacol has been primarily detected in urine. 4-Vinylguaiacol exists in all eukaryotes, ranging from yeast to humans. 4-Vinylguaiacol is a clove, curry, and peanut tasting compound that can be found in a number of food items such as citrus, spearmint, coffee, and beer. This makes 4-vinylguaiacol a potential biomarker for the consumption of these food products.
Structure
Thumb
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
DescriptionThis compound belongs to the class of organic compounds known as methoxyphenols. These 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udr-6900000000-c95e8007869a915d6fe6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udr-6900000000-c95e8007869a915d6fe6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uki-2900000000-6a52b2fb0cd2b1888cbaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-8970000000-109c9889992939114454View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-9de02cce24e40d1314afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-04be6d79c3fa5851d78dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9300000000-bab367ece5e140a11583View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-cd337f7259f32e912e8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-5cef2e884a5445e8509bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-7900000000-27870d0d63eeb1b6290dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0ug0-9700000000-32bccf98e351d8308924View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationNot 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
FoodDB 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
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