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Showing Compound 2-Methoxy-4-vinylphenol (FDB000857)

Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2019-11-26 02:55:32 UTC
Primary IDFDB000857
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 exists in all eukaryotes, ranging from yeast 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, carrots, and red wines and in a lower concentration in sesames, beers, and kohlrabis. 2-Methoxy-4-vinylphenol has also been detected, but not quantified in, several different foods, such as spearmints, tortilla chips, citrus, oats, and sweet oranges. This could make 2-methoxy-4-vinylphenol a potential biomarker for the consumption of these foods.
CAS Number7786-61-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
2-Methoxy-4-Vinyl-Phenolbiospider
2-Methoxy-4-vinylphenoldb_source
2-metoxy-4-vinyl-phenolbiospider
4-Vinyl guaiacolbiospider
4-vinyl-2-methoxyphenolbiospider
4-Vinyl-2-methoxyphenol ( P-vinylguaiacol)HMDB
EUGbiospider
Hesperetoldb_source
O-methoxy-p-vinylphenolbiospider
P-vinyl guaiacolbiospider
P-vinyl guaicolbiospider
P-vinylguaiacolbiospider
Phenol, 4-ethenyl-2-methoxy-biospider
Vinylcatechol-o-methyl ether, p-biospider
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
Chemical FormulaC9H10O2
IUPAC name4-ethenyl-2-methoxyphenol
InChI IdentifierInChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3
InChI KeyYOMSJEATGXXYPX-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(C=C)=CC=C1O
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.98%; H 6.71%; O 21.31%DFC
Melting PointMp 57°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data312 (e 8900) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0ug0-9700000000-32bccf98e351d8308924Spectrum
GC-MS2-Methoxy-4-vinylphenol, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-c95e8007869a915d6fe6Spectrum
GC-MS2-Methoxy-4-vinylphenol, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-c95e8007869a915d6fe6Spectrum
Predicted GC-MS2-Methoxy-4-vinylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uki-2900000000-6a52b2fb0cd2b1888cbaSpectrum
Predicted GC-MS2-Methoxy-4-vinylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-8970000000-109c9889992939114454Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9800000000-56d5ac2538cf6e556070Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000i-9000000000-e8dab5adaa22e054ee21Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-0ecf25f0ebb081e29570Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-001i-0900000000-90c9c5c165a18a64dbb3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-9de02cce24e40d1314afSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-04be6d79c3fa5851d78dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9300000000-bab367ece5e140a11583Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-cd337f7259f32e912e8aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-5cef2e884a5445e8509bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-7900000000-27870d0d63eeb1b6290dSpectrum
NMR
TypeDescriptionView
ChemSpider ID325
ChEMBL IDCHEMBL1232595
KEGG Compound IDC17883
Pubchem Compound ID332
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID632
DrugBank IDDB03514
HMDB IDHMDB13744
CRC / DFC (Dictionary of Food Compounds) IDBRG84-D:BKH58-G
EAFUS ID2225
Dr. Duke IDP-VINYL-GUAIACOL|4-VINYL-GUAIACOL|2-METHOXY-4-VINYL-PHENOL
BIGG IDNot Available
KNApSAcK IDC00029546
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID7786-61-0
GoodScent IDrw1005101
SuperScent ID332
Wikipedia ID2-Methoxy-4-vinylphenol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti edemicDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
pheromone26013 A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
clove
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
curry
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
peanut
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
smoky
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.