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Record Information
Version5.0
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-hydroxy-3-methoxystyrene or 4-vinylguaiacol, 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 exists in all eukaryotes, ranging from yeast to plants to humans. 2-Methoxy-4-vinylphenol is a clove, curry, and peanut tasting compound. 2-Methoxy-4-vinylphenol is found, on average, in the highest concentration within a few different foods, such as wild carrots (Daucus carota), carrots (Daucus carota ssp. sativus), and red wine and in a lower concentration in arabica coffees (Coffea arabica), kohlrabis (Brassica oleracea var. gongylodes), and beer. 2-Methoxy-4-vinylphenol has also been detected, but not quantified in, several different foods, such as oats (Avena sativa), tortilla, asparagus (Asparagus officinalis), spearmints (Mentha spicata), and tortilla chip. This could make 2-methoxy-4-vinylphenol a potential biomarker for the consumption of these foods. 2-Methoxy-4-vinylphenol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 2-Methoxy-4-vinylphenol.
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

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.42 g/LALOGPS
logP10(1.84) g/LALOGPS
logP10(2.25) g/LChemAxon
logS10(-1.3) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.04631661259
DarkChem[M-H]-132.09131661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methoxy-4-vinylphenol,1TMS,#1C=CC1=CC=C(O[Si](C)(C)C)C(OC)=C11409.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Methoxy-4-vinylphenol,1TBDMS,#1C=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C11660.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Methoxy-4-vinylphenol EI-B (Non-derivatized)splash10-0udr-6900000000-c95e8007869a915d6fe62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methoxy-4-vinylphenol EI-B (Non-derivatized)splash10-0udr-6900000000-c95e8007869a915d6fe62018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methoxy-4-vinylphenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uki-2900000000-6a52b2fb0cd2b1888cba2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methoxy-4-vinylphenol GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-8970000000-109c98899929391144542017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methoxy-4-vinylphenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ug0-9700000000-32bccf98e351d83089242015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol LC-ESI-QFT , positive-QTOFsplash10-000i-9800000000-56d5ac2538cf6e5560702020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol LC-ESI-QTOF 35V, positive-QTOFsplash10-000i-9000000000-e8dab5adaa22e054ee212020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol LC-ESI-QFT , negative-QTOFsplash10-0a4i-0900000000-0ecf25f0ebb081e295702020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol LC-ESI-QTOF 35V, negative-QTOFsplash10-001i-0900000000-90c9c5c165a18a64dbb32020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 35V, Negative-QTOFsplash10-001i-0900000000-90c9c5c165a18a64dbb32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 35V, Positive-QTOFsplash10-000i-9100000000-4fc1449d3b5ebcebcddc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 10V, Negative-QTOFsplash10-001i-0900000000-07c85f81abcab35c8c852021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 40V, Negative-QTOFsplash10-0c00-9200000000-e9c17a72d9b795c9cadc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 20V, Negative-QTOFsplash10-001i-0900000000-142267324f6352c647e42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 10V, Positive-QTOFsplash10-0udi-0900000000-9de02cce24e40d1314af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 20V, Positive-QTOFsplash10-0udi-1900000000-04be6d79c3fa5851d78d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 40V, Positive-QTOFsplash10-0fb9-9300000000-bab367ece5e140a115832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 10V, Negative-QTOFsplash10-0002-0900000000-cd337f7259f32e912e8a2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 20V, Negative-QTOFsplash10-0002-0900000000-5cef2e884a5445e8509b2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 40V, Negative-QTOFsplash10-00o0-7900000000-27870d0d63eeb1b6290d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 10V, Positive-QTOFsplash10-0uxr-1900000000-3df4f1c76f8984133ce72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 20V, Positive-QTOFsplash10-0gdl-7900000000-5c60e1bd99afb019139f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 40V, Positive-QTOFsplash10-0fb9-9000000000-51462e1d8e8381a727122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 10V, Negative-QTOFsplash10-0002-0900000000-e0b12c10ffeec106d7592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 20V, Negative-QTOFsplash10-001i-1900000000-dae1e2e32bbe62db4e5a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxy-4-vinylphenol 40V, Negative-QTOFsplash10-014i-6900000000-c0a65988d269dc5278a82021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal
    • Zhang, S., Liu, L...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
MarkerDB IDNot Available
Good Scents 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