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(+)-taxifolin (FDB030075)

Record Information
Version1.0
Creation date2015-05-07 18:34:01 UTC
Update date2019-11-26 03:21:35 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
OntologyNo ontology term
Physico-Chemical Properties
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-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 25V, Negativesplash10-00fr-0591000000-8c2bb267dbaff0ec84252017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0fk9-0393000000-2ad9cdbeaebe4832addf2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0019000000-f4c2db21ffbf7fdec0ec2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 25V, Negativesplash10-00fr-0591000000-8c2bb267dbaff0ec84252017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0fk9-0393000000-2ad9cdbeaebe4832addf2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0019000000-f4c2db21ffbf7fdec0ec2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0pc1-0980000000-2d1ecd15f61d12518b212017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-004r-0960000000-22428e71371e23f8c0f12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4r-0965000000-d0ca2227f5b5c9adb5092017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0190000000-5cfd8e48c0ba0adace9c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0190000000-4e9899457ae22ca1e3a82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00fr-0591000000-8c2bb267dbaff0ec84252017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0fk9-0393000000-2ad9cdbeaebe4832addf2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0090000000-1c45a54959ecd51d86152017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4r-0965000000-d0ca2227f5b5c9adb5092017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0ul1-0930000000-805f5b6770fe1b1ed7992017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 21V, positivesplash10-052r-0290000000-107edeec1397159412152020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 21V, positivesplash10-0k9i-0490000000-54689ad702b3a9efd3312020-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0229000000-ca2358a4a03140a288002016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-0932000000-8fe616c50e11538a79d22016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-3900000000-055fc061b8b4ca3c7e7d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0319000000-14f9f888c64a721095192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0923000000-2e407916474c282025532016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4910000000-da486b0c8e7b8f7c2a402016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-af408fd7a67d4a98dd0c2021-10-21View Spectrum
NMRNot Available
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
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
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