Record Information
Version1.0
Creation date2010-04-08 22:09:23 UTC
Update date2019-11-26 03:04:24 UTC
Primary IDFDB010971
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxy-2H-1-benzopyran-2-one
Description4-Hydroxy-2H-1-benzopyran-2-one belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 4-Hydroxy-2H-1-benzopyran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxy-2H-1-benzopyran-2-one is found, on average, in the highest concentration within grape wines and beers. This could make 4-hydroxy-2H-1-benzopyran-2-one a potential biomarker for the consumption of these foods.
CAS Number1076-38-6
Structure
Thumb
Synonyms
SynonymSource
2-Hydroxy-4H-1-benzopyran-4-onedb_source
2-Hydroxychromonedb_source
2H-1-Benzopyran-2-one, 4-hydroxy-biospider
2H-1-Benzopyran-2,4(3H)-dionedb_source
3-(4-Hydroxyphenyl)-1-propaneHMDB
3-OHPPHMDB
4-Coumarinolmanual
4-Hydroxy-2H-chromen-2-onebiospider
4-Hydroxycinnamyl alcoholChEBI
4-Hydroxycoumarindb_source
4-Hydroxycoumarinebiospider
Benzotetronatebiospider
Benzotetronic aciddb_source
Coumarin, 4-hydroxy-biospider
Hydroxy coumarinHMDB
P-Coumaryl alcoholChEBI
Predicted Properties
PropertyValueSource
Water Solubility3.55 g/LALOGPS
logP0.75ALOGPS
logP1.81ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)5.48ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity52.57 m³·mol⁻¹ChemAxon
Polarizability15.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H6O3
IUPAC name2-hydroxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,11H
InChI KeyOWBBAPRUYLEWRR-UHFFFAOYSA-N
Isomeric SMILESOC1=CC(=O)C2=CC=CC=C2O1
Average Molecular Weight162.144
Monoisotopic Molecular Weight162.031694053
Classification
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Chromone
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 66.67%; H 3.73%; O 29.60%DFC
Melting PointMp 232-233°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data262 (e 11900) (EtOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Hydroxy-2H-1-benzopyran-2-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-045c-3900000000-4a2fc840ec22a83d909eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-9975e24c3ae0661c2ee6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-6fff3bff2c39de5e55e0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-7900000000-aa26a1d2ff6b75b366a9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-700569317f85cc30b3b1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-842ec05607fb73b39974Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9400000000-d57d27787cee8ff65bd0Spectrum
NMRNot Available
ChemSpider ID4444166
ChEMBL IDCHEMBL109034
KEGG Compound IDC02646
Pubchem Compound ID5280535
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID642
DrugBank IDDB03410
HMDB IDHMDB03654
CRC / DFC (Dictionary of Food Compounds) IDFXG77-L:FXG77-L
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2299830
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID4-Hydroxycoumarins
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
Enzymes
NameGene NameUniProt ID
Peroxiredoxin-6PRDX6P30041
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
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.