Record Information
Version1.0
Creation date2015-05-07 18:34:01 UTC
Update date2018-05-29 01:54:50 UTC
Primary IDFDB030075
Secondary Accession Numbers
  • FDB002749
Chemical Information
FooDB Name(+)-taxifolin
DescriptionTaxifolin, also known as dihydroquercetin or (+)-taxifolin, is a member of the class of compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively. Taxifolin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Taxifolin can be found in a number of food items such as sweet rowanberry, arrowroot, evening primrose, and walnut, which makes taxifolin a potential biomarker for the consumption of these food products. Taxifolin is a flavanonol, a type of flavonoid .
CAS Number480-18-2
Structure
Thumb
Synonyms
SynonymSource
(+)-DihydroquercetinChEBI
(2R,3R)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-oneChEBI
(2R,3R)-DihydroquercetinChEBI
(2R-trans)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4-benzopyroneChEBI
DihydroquercetinChEBI
trans-DihydroquercetinChEBI
(+)-TaxifolinKegg
2,3-trans-DihydroquercetinChEBI
TaxifolinChEBI
Predicted Properties
PropertyValueSource
Water Solubility1.16 g/LALOGPS
logP1.07ALOGPS
logP1.82ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)7.74ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.61 m³·mol⁻¹ChemAxon
Polarizability29.03 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H12O7
IUPAC name(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,14-19,21H/t14-,15+/m0/s1
InChI KeyCXQWRCVTCMQVQX-LSDHHAIUSA-N
Isomeric SMILESO[C@@H]1[C@H](OC2=C(C(O)=CC(O)=C2)C1=O)C1=CC=C(O)C(O)=C1
Average Molecular Weight304.2516
Monoisotopic Molecular Weight304.058302738
Classification
Description belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanonols
Alternative Parents
Substituents
  • Hydroxyflavonoid
  • Flavanonol
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Chromane
  • Catechol
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyShould have ontology for this compound
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
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 25V, Negativesplash10-00fr-0591000000-8c2bb267dbaff0ec8425View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0fk9-0393000000-2ad9cdbeaebe4832addfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0019000000-f4c2db21ffbf7fdec0ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 25V, Negativesplash10-00fr-0591000000-8c2bb267dbaff0ec8425View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0fk9-0393000000-2ad9cdbeaebe4832addfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0019000000-f4c2db21ffbf7fdec0ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0pc1-0980000000-2d1ecd15f61d12518b21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-004r-0960000000-22428e71371e23f8c0f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4r-0965000000-d0ca2227f5b5c9adb509View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0190000000-5cfd8e48c0ba0adace9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0190000000-4e9899457ae22ca1e3a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00fr-0591000000-8c2bb267dbaff0ec8425View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0fk9-0393000000-2ad9cdbeaebe4832addfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0090000000-1c45a54959ecd51d8615View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4r-0965000000-d0ca2227f5b5c9adb509View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ul1-0930000000-805f5b6770fe1b1ed799View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0229000000-ca2358a4a03140a28800View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-0932000000-8fe616c50e11538a79d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-3900000000-055fc061b8b4ca3c7e7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0319000000-14f9f888c64a72109519View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0923000000-2e407916474c28202553View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4910000000-da486b0c8e7b8f7c2a40View in MoNA
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) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET 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
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference