Record Information
Version1.0
Creation date2010-04-08 22:05:30 UTC
Update date2018-05-28 23:09:46 UTC
Primary IDFDB002749
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTaxifolin
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 cloudberry, macadamia nut (m. tetraphylla), oregon yampah, and nectarine, 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
(+)-trans-3,3',4',5,7-Pentahydroxyflavanonedb_source
2R,3R-Dihydroquercetinbiospider
Distylindb_source
Taxifolioldb_source
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.22%; H 3.98%; O 36.81%DFC
Melting PointMp 240-242° (221-222°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP0.95PERRISSOUD,D & TESTA,B (1986)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]24D +44 (c, 1.03 in 50% Me2CO aq.)DFC
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 ID10185
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID117
DrugBank IDDB02224
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCNL06-P:CNL07-Q
EAFUS IDNot Available
Dr. Duke IDTAXIFOLIN
BIGG IDNot Available
KNApSAcK IDC00000677
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID117
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti complementaryDUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti mutagenicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
oxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
RNA-genicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— 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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).