Record Information
Version1.0
Creation date2010-04-08 22:09:53 UTC
Update date2018-05-29 00:54:28 UTC
Primary IDFDB011897
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuercetagetin
Description2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one, also known as 6-hydroxyquercetin or 3,3',4',5,6,7-hexahydroxyflavone, is a member of the class of compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one can be synthesized from quercetin. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is also a parent compound for other transformation products, including but not limited to, axillarin, eupatin, and patuletin. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is a bitter tasting compound found in sweet orange, which makes 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one a potential biomarker for the consumption of this food product.
CAS Number90-18-6
Structure
Thumb
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4-benzopyroneChEBI
3,3',4',5,6,7-HexahydroxyflavoneChEBI
6-HydroxyquercetinChEBI
2-(3,4-Dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4H-1-benzopyran-4-one, 9CIdb_source
3',4',5,6,7-Pentahydroxyflavonoldb_source
Quercetagetindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP1.7ALOGPS
logP1.85ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.56ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area147.68 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity78.84 m³·mol⁻¹ChemAxon
Polarizability29.49 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H10O8
IUPAC name2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)15-14(22)13(21)10-9(23-15)4-8(18)11(19)12(10)20/h1-4,16-20,22H
InChI KeyZVOLCUVKHLEPEV-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=C(C(O)=C1O)C(=O)C(O)=C(O2)C1=CC(O)=C(O)C=C1
Average Molecular Weight318.2351
Monoisotopic Molecular Weight318.037567296
Classification
Description belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3-hydroxyflavone
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 6-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 56.61%; H 3.17%; O 40.22%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 Data361 (e 21877) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0900-1212109000-3d0cb1e71bc3f80f051eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-0792000000-663986ef797f12ea62e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-e0804a88f8274e655f90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0349000000-4d74a79028a275bf77d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l6r-4920000000-691c34c0f5798b9cc754View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0119000000-1642b5f1d7c819f7c757View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0479000000-ed9d9b0a589026bce21bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-7940000000-0ef9c3a3a5bb3639b66cView 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 ID354
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHBP96-H:HBP96-H
EAFUS IDNot Available
Dr. Duke IDQUERCETAGETIN
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 / 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 HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
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
dye37958 DUKE
HIV-reverse-transcriptase 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
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).