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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-05-18 14:35:48 UTC
Update Date2017-12-07 02:43:39 UTC
HMDB IDHMDB0013744
Secondary Accession Numbers
  • HMDB13744
Metabolite Identification
Common Name2-Methoxy-4-vinylphenol
Description4-vinylguaiacol, also known as 4-vinyl-2-methoxyphenol or 4-hydroxy-3-methoxystyrene, is a member of the class of 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 is a clove, curry, and peanut tasting compound and can be found in a number of food items such as corn, coffee, wild carrot, and garden tomato (var.), which makes 4-vinylguaiacol a potential biomarker for the consumption of these food products. 4-vinylguaiacol can be found primarily in urine. 4-vinylguaiacol exists in all eukaryotes, ranging from yeast to humans. Ferulic acid is converted by certain strains of yeast, notably strains used in brewing of wheat beers, such as Torulaspora delbrueckii to 2-methoxy-4-vinylphenol which gives beers such as Weissbier and Wit their distinctive "clove" flavor. Saccharomyces cerevisiae (brewer's yeast) and Pseudomonas fluorescens are also able to convert trans-ferulic acid into 2-methoxy-4-vinylphenol (Wikipedia). 2-Methoxy-4-vinylphenol is an aromatic substance used as a flavoring agent. It is one of the compounds responsible for the natural aroma of buckwheat..
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
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
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
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)
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease ReferencesNone
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