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4-Vinylphenol (YMDB01627)

Identification
YMDB IDYMDB01627
Name4-Vinylphenol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description4-Vinylphenol is a vinylphenol, a type of pyranoanthocyanin. 4-Vinylphenol is produced by decarboxylation by phenyl acrylic acid decarboxylase of the grape compound p-coumaric acid by certain strains of S. cerevisiae. Vinylphenols then spontaneously condensate with grape anthocyanins (mainly malvidin-3-O-glucoside) to form pigments important for the color of ageing wine. 4-Vinylphenol is responsible for a hospital or plaster smell. [PMID: 17303275]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 4-Hydroxystyrene
  • p-Vinylphenol
  • 4-Vinylphenol
  • p-Hydroxystyrene
CAS number2628-17-3
WeightAverage: 120.1485
Monoisotopic: 120.057514878
InChI KeyFUGYGGDSWSUORM-UHFFFAOYSA-N
InChIInChI=1S/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2
IUPAC Name4-ethenylphenol
Traditional IUPAC Name4-vinylphenol
Chemical FormulaC8H8O
SMILESOC1=CC=C(C=C)C=C1
Chemical Taxonomy
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-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point73.5 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility8.4 g/LALOGPS
logP2.07ALOGPS
logP2.41ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.56ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.73 m³·mol⁻¹ChemAxon
Polarizability13.15 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0900000000-78e97f8689a1bddce8d1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004l-1900000000-aabb90db206495e1949cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0900000000-78e97f8689a1bddce8d1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004l-1900000000-aabb90db206495e1949cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-e4b2ae72210dba8376c5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fu-8900000000-96525d05990bd44a73e6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-4748791daa3cc6db33cbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-b529604eb0086ce7d85aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-cc4e2accb5dbfca1223aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9300000000-1a680f497983265f7000JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-992515c0effcfff51739JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-adf06e57ffef41aa20d0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-9600000000-7855fd6420cc0a980f56JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-2c381eb3871f5dbd6a94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-9800000000-e2093cd31e1a5d12f825JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9000000000-dd7dfadb6034e83a56c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-972f865a96261dcb891aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3900000000-cc2986e6d45482e40a36JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0i2d-9000000000-6a5b5c88ab894e1f7233JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID1883
HMDB IDHMDB04072
Pubchem Compound ID13493582
Kegg IDC05627
ChemSpider ID56234
FOODB IDFDB010540
Wikipedia IDNot Available
BioCyc IDNot Available