Record Information
Version1.0
Creation date2010-04-08 22:09:58 UTC
Update date2020-02-24 19:11:09 UTC
Primary IDFDB012057
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBaicalein
DescriptionBaicalein, also known as 5,6,7-trihydroxyflavone or baicalein (old), is a member of the class of compounds known as flavones. Flavones are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, baicalein is considered to be a flavonoid lipid molecule. Baicalein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Baicalein can be found in welsh onion, which makes baicalein a potential biomarker for the consumption of this food product. Baicalein, along with its analogue baicalin, is a positive allosteric modulator of the benzodiazepine site and/or a non-benzodiazepine site of the GABAA receptor. It displays subtype selectivity for α2 and α3 subunit-containing GABAA receptors. In accordance, baicalein shows anxiolytic effects in mice without incidence of sedation or myorelaxation. It is thought that baicalein, along with other flavonoids, may underlie the anxiolytic effects of S. baicalensis and S. lateriflora. Baicalein is also an antagonist of the estrogen receptor, or an antiestrogen .
CAS Number491-67-8
Structure
Thumb
Synonyms
SynonymSource
5,6,7-TrihydroxyflavoneChEBI
Baicalein (old)HMDB
5,6,7-Trihydroxy-2-phenyl-4H-1-benzopyran-4-one, 9CIdb_source
Baicaleindb_source
Noroxylindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP3.19ALOGPS
logP2.71ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.76ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.91 m³·mol⁻¹ChemAxon
Polarizability26.67 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H10O5
IUPAC name5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one
InChI IdentifierInChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H
InChI KeyFXNFHKRTJBSTCS-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=C(C(O)=C1O)C(=O)C=C(O2)C1=CC=CC=C1
Average Molecular Weight270.2369
Monoisotopic Molecular Weight270.05282343
Classification
Description Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • 5-hydroxyflavonoid
  • 6-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.67%; H 3.73%; O 29.60%DFC
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 Data323 (e 17780) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBaicalein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f6x-0690000000-26c3415c0019e9305302Spectrum
Predicted GC-MSBaicalein, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0229-3432900000-21148b993bd61bb599dbSpectrum
Predicted GC-MSBaicalein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBaicalein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0910000000-4cc66ae52ae7f30ab947Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-2b0a90a93bbc833a5622Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-3b007f8a59433c8c8102Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-3b007f8a59433c8c8102Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 18V, positivesplash10-00di-0090000000-2b556d7b585d517b4b16Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 18V, positivesplash10-0fk9-0190000000-259e40faeec23ba7a19aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-d057d8da86138dd0be8aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0190000000-9f02f815afd10e8b5021Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2920000000-5145494ff84c051688b5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-aed0ef161d0e7596d809Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0190000000-7908c9e1a7c69c8f90afSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4920000000-b9f5b2c4aa5f8eb26a05Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-60b322ff74af8a765580Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-60b322ff74af8a765580Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-0940000000-7bca73ace96babecfa87Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-64c0ecfe6a05ff374370Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-f4d4f75e0d42704d6c79Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0920000000-cca492b9d35862e6e36fSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10023
Pubchem Compound ID12214328
Pubchem Substance IDNot Available
ChEBI ID2979
Phenol-Explorer ID266
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHCW36-F:HCW36-F
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.