Record Information
Version1.0
Creation date2010-04-08 22:09:10 UTC
Update date2019-11-26 03:03:44 UTC
Primary IDFDB010539
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Vinylphenol
Description2-vinylphenol is a member of the class of compounds known as styrenes. Styrenes are organic compounds containing an ethenylbenzene moiety. 2-vinylphenol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 2-vinylphenol can be found in ceylon cinnamon and chinese cinnamon, which makes 2-vinylphenol a potential biomarker for the consumption of these food products. 2-vinylphenol is a phenolic compound found in wine and beer. It is produced by the spoilage yeast Brettanomyces. When it reaches concentrations greater than the sensory threshold, it can give the wine aromas described as barnyard, medicinal, band-aids, and mousy. In wine, 4-vinylphenol can react with other molecules, such as anthocyanidins, to produce new chemical compounds. In white wines vinylphenols are dominant (4-vinylphenol 70-1 150 μg/l, 4-vinylguajacol 10-490 μg/l) whereas, in red wines, it's the corresponding ethyl-phenols .
CAS Number695-84-1
Structure
Thumb
Synonyms
SynonymSource
(2-Hydroxyphenyl)ethylenedb_source
2-Ethenylphenol, 9CIdb_source
2-Hydroxystyrenedb_source
Predicted Properties
PropertyValueSource
Water Solubility8.56 g/LALOGPS
logP2.11ALOGPS
logP2.41ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.73 m³·mol⁻¹ChemAxon
Polarizability13.04 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O
IUPAC name2-ethenylphenol
InChI IdentifierInChI=1S/C8H8O/c1-2-7-5-3-4-6-8(7)9/h2-6,9H,1H2
InChI KeyJESXATFQYMPTNL-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=CC=C1C=C
Average Molecular Weight120.1485
Monoisotopic Molecular Weight120.057514878
Classification
Description Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassStyrenes
Direct ParentStyrenes
Alternative Parents
Substituents
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 79.97%; H 6.71%; O 13.32%DFC
Melting PointNot Available
Boiling PointBp15 165°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd18 1.06DFC
Refractive Indexn20D 1.5851DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Vinylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9800000000-db0dc188d7d34a22b04dSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-413df47b2ddc83626921Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-5900000000-8e5741cf716a9268d075Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-9200000000-cf040088e7a5b850a108Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-57c140692ae0e2d7949dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-790a7a29cd1936826c79Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-24335b3d408e7186506cSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDFCN70-W:FCN70-W
EAFUS IDNot Available
Dr. Duke ID2-VINYLPHENOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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).