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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-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 white wine, coffees (Coffea), and robusta coffees (Coffea canephora). 2-Methoxy-4-vinylphenol has also been detected, but not quantified in, several different foods, such as taco, citrus, celery stalks (Apium graveolens var. dulce), evergreen blackberries (Rubus laciniatus), and tortilla chip. This could make 2-methoxy-4-vinylphenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Methoxy-4-vinylphenol.
CAS Number7786-61-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not 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
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)splash10-0ug0-9700000000-32bccf98e351d83089242015-03-01View Spectrum
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
Predicted GC-MS2-Methoxy-4-vinylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9800000000-56d5ac2538cf6e5560702020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000i-9000000000-e8dab5adaa22e054ee212020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-0ecf25f0ebb081e295702020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-001i-0900000000-90c9c5c165a18a64dbb32020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-90c9c5c165a18a64dbb32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9100000000-4fc1449d3b5ebcebcddc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-07c85f81abcab35c8c852021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0c00-9200000000-e9c17a72d9b795c9cadc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-142267324f6352c647e42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-9de02cce24e40d1314af2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-04be6d79c3fa5851d78d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9300000000-bab367ece5e140a115832016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-cd337f7259f32e912e8a2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-5cef2e884a5445e8509b2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-7900000000-27870d0d63eeb1b6290d2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-1900000000-3df4f1c76f8984133ce72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gdl-7900000000-5c60e1bd99afb019139f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9000000000-51462e1d8e8381a727122021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e0b12c10ffeec106d7592021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-dae1e2e32bbe62db4e5a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-6900000000-c0a65988d269dc5278a82021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
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.