Record Information
Version1.0
Creation date2010-04-08 22:04:32 UTC
Update date2019-11-26 02:54:38 UTC
Primary IDFDB000336
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Vinylsyringol
Description4-vinylsyringol is a member of the class of compounds known as stilbenes. Stilbenes are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 4-vinylsyringol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 4-vinylsyringol can be found in rape, which makes 4-vinylsyringol a potential biomarker for the consumption of this food product. 4-vinylsyringol is a phenolic compound found in crude canola oil. It is produced by decarboxylation of sinapic acid during canola seed roasting .
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
2,6-Dimethoxy-4-vinylphenoldb_source
4-hydroxy-3,5-dimethoxystyrenedb_source
4-Vinyl-2,6-dimethoxyphenoldb_source
4-Vinyl-2,6-dimethoxyphenol (4-vinylsyringol)biospider
Canololdb_source
Phenol, 4-ethenyl, 2,6-dimethoxybiospider
Predicted Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP3.16ALOGPS
logP3.55ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.94 m³·mol⁻¹ChemAxon
Polarizability26.46 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H14O3
IUPAC name3-methoxy-5-[(E)-2-phenylethenyl]benzene-1,2-diol
InChI IdentifierInChI=1S/C15H14O3/c1-18-14-10-12(9-13(16)15(14)17)8-7-11-5-3-2-4-6-11/h2-10,16-17H,1H3/b8-7+
InChI KeyWBBHYMRWGHBXLS-BQYQJAHWSA-N
Isomeric SMILESCOC1=CC(\C=C\C2=CC=CC=C2)=CC(O)=C1O
Average Molecular Weight242.2699
Monoisotopic Molecular Weight242.094294314
Classification
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Methoxyphenol
  • Anisole
  • Catechol
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen 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 CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Vinylsyringol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-1290000000-8c6a2e45d9884f2a81d4Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-93fcd1fcd6db2f0a3374Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-3890000000-1f5695abbec8887f1024Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufu-4900000000-5db5fd8cfeb9d2dda712Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-b6a7203651c20143671cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0290000000-922ca674148f00ef6b62Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-3940000000-9e4cca64ce5a62a87dfbSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID24148525
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID634
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
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— 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.