Record Information
Version1.0
Creation date2010-04-08 22:09:53 UTC
Update date2020-09-17 15:33:11 UTC
Primary IDFDB011904
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuercetin
DescriptionQuercetin, also known as sophoretin or xanthaurine, 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. Quercetin is an antioxidant, like many other phenolic heterocyclic compounds. Quercetin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Quercetin is a widely distributed flavonoid found in many plants and fruits including red grapes, citrus fruit, tomatoes, broccoli, red onions, kale, various leafy green vegetables, and a number of berries, including raspberries and cranberries. In plants quercetin functions as a naturally occurring polar auxin transport inhibitor (PMID: 12237347). Quercetin has a bitter flavor and is used as an ingredient in dietary supplements, beverages, and foods. Quercetin itself (the aglycone), as opposed to quercetin glycosides, is not a normal dietary component. Quercitin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. In the human body quercetin functions as a non-specific protein kinase enzyme inhibitor (PMID: 15019969). It also acts as a phytoestrogen and has been reported to have estrogenic activities by activating both estrogen receptor alpha (ER alpha) and estrogen beta (ER beta) (PMID: 17724002). In human breast cancer cell lines, quercetin has been found to act as an agonist of the G protein-coupled estrogen receptor (GPER) (PMID: 15090535). Despite these many known interactions with human proteins, quercetin has not been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. In particular, the U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, there is a clear inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adjustment for known risk factors and other dietary components. A limited number of intervention studies with flavonoids and flavonoid containing foods and extracts has been performed in several pathological conditions. (PMID: 17015250).
CAS Number117-39-5
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP1.81ALOGPS
logP2.16ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.86 m³·mol⁻¹ChemAxon
Polarizability28.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H10O7
IUPAC name2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C15H10O7/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/h1-5,16-19,21H
InChI KeyREFJWTPEDVJJIY-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1
Average Molecular Weight302.2357
Monoisotopic Molecular Weight302.042652674
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
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MSQuercetin, 5 TMS, GC-MS Spectrumsplash10-0bt9-2611390000-f8e98c928a7ed82acda4Spectrum
    GC-MSQuercetin, non-derivatized, GC-MS Spectrumsplash10-0bt9-2611390000-f8e98c928a7ed82acda4Spectrum
    Predicted GC-MSQuercetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-0591000000-2a146657da898ec9322eSpectrum
    Predicted GC-MSQuercetin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00l2-2093078000-1de46637305246feffd2Spectrum
    Predicted GC-MSQuercetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0009000000-d4689b76f41c734873992012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0967000000-613e61ec0c69ed0ee6302012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0uy0-5910000000-ee816015eec26c8621b12012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-0udi-0009000000-ec1cab852ed9f9f78fa42012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-1907000000-6f36df2733dadae380c22012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0309000000-976a99c106ceca16d73b2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0pi0-1900000000-b2e286366d41e47dd8fc2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0209000000-e891863ec110aeb660b02012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0940000000-aa52db00c1defe3ccf752012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0219000000-5ef285c4b6bfd220b8b12012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0219000000-547c83bb70e7da007d6c2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-1907000000-a59602c09f66e96560682012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-0udi-0009000000-4416f39adf6c9b919bfa2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0udi-0019000000-eb14ec62fc2fb2f1da882012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0ufr-0910000000-0730bca525c17aac75c52012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0030290000-06238e4a98a4daad32652017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0039008002-9df3edfb34deb15f84742017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0039008002-9df3edfb34deb15f84742017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0uka-0193000000-3325ca1a080730a9c0bf2017-08-14View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-ee8570ac70818e8939bb2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0279000000-71b5db7ef8322cc8b9e92016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zg0-7960000000-7edbb229853a642749ac2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-21580b9d8394d2eea3a52016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0239000000-b77fcb9c0ce11dc515bf2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0apr-5940000000-0590bdee504c5ed6ba362016-09-12View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
    ChemSpider ID4444051
    ChEMBL IDCHEMBL50
    KEGG Compound IDC00389
    Pubchem Compound ID5280343
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID291
    DrugBank IDDB04216
    HMDB IDHMDB05794
    CRC / DFC (Dictionary of Food Compounds) IDHBR39-C:HBR39-C
    EAFUS IDNot Available
    Dr. Duke IDQUERCETIN
    BIGG IDNot Available
    KNApSAcK IDC00004631
    HET IDQUE
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDQuercetin
    Phenol-Explorer Metabolite ID291
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    Processing...
    Biological Effects and Interactions
    Health Effects / Bioactivities
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    Files
    MSDSshow
    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.
    — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.