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Record Information
Version	2.0
Creation Date	2012-10-10 12:21:51 -0600
Update Date	2015-09-13 15:15:34 -0600
Secondary Accession Numbers	ECMDB23201
Identification
Name:	Quercetin
Description	Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. In E. coli it is metabolized by Quercetin 2,3-dioxygenase. This enzyme catalyzes the reaction Quercetin + O2 = 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate + CO + H+. Quercetin is not a normal growth substrate for E. coli but it is found in high levels in the human gut. This enzyme may have evolved to break down quercitin to prevent its inhibition of key E. coli proteins, such as DNA gyrase.
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xb260c4a0> Close
Synonyms:	2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chromen-4-one 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one 3',4',5,7-tetrahydroxy-3-methoxyflavone 3',4',5,7-Tetrahydroxyflavan-3-ol 3',4',5,7-tetrahydroxyflavon-3-ol 3,3',4',5,7-pentahydroxyflavone 3,3',4,5,7-Pentahydroxyflavone 3,4',5,5',7-pentahydroxy-Flavone 3,5,7,3',4'-Pentahydroxyflavone 3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-on 3-methoxy-5,7,3',4'-tetrahydroxyflavone 3-methoxyluteolin Flavin meletin Meletin Quercetin dihydrate Quercetin dihydric acid Quercetol Quertin Sophoretin Xanthaurine
Chemical Formula:	C15H10O7
Weight:	Average: 302.2357 Monoisotopic: 302.042652674
InChI Key:	REFJWTPEDVJJIY-UHFFFAOYSA-N
InChI:	InChI=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
CAS number:	117-39-5
IUPAC Name:	2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
Traditional IUPAC Name:	quercetin
SMILES:	OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1
Chemical Taxonomy
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.
Kingdom	Organic compounds
Super Class	Phenylpropanoids and polyketides
Class	Flavonoids
Sub Class	Flavones
Direct Parent	Flavonols
Alternative Parents	3'-hydroxyflavonoids 3-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Chromones Catechols 1-hydroxy-2-unsubstituted benzenoids Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Vinylogous acids Heteroaromatic compounds Oxacyclic compounds Polyols Hydrocarbon derivatives Organic oxides
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 Framework	Aromatic heteropolycyclic compounds
External Descriptors	pentahydroxyflavone (CHEBI:16243 ) 7-hydroxyflavonol (CHEBI:16243 ) flavonols (C00389 ) Flavones and Flavonols (C00389 ) Flavones and Flavonols (LMPK12110004 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	316 - 318 C
Experimental Properties:	Property Value Source Water Solubility: 0.06 mg/mL at 16 oC [SEIDELL,A (1941)] PhysProp
Predicted Properties	Property Value Source Water Solubility 0.26 g/L ALOGPS logP 1.81 ALOGPS logP 2.16 ChemAxon logS -3.1 ALOGPS pKa (Strongest Acidic) 6.38 ChemAxon pKa (Strongest Basic) -4 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 127.45 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 76.86 m³·mol⁻¹ ChemAxon Polarizability 28.54 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Quercetin + Oxygen > 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate + CO + Hydrogen ion
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-MS (5 TMS) splash10-0bt9-2611390000-f8e98c928a7ed82acda4 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0bt9-2611390000-f8e98c928a7ed82acda4 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0079-0591000000-2a146657da898ec9322e View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive splash10-00l2-2093078000-1de46637305246feffd2 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-0udi-0009000000-d4689b76f41c73487399 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-0udi-0967000000-613e61ec0c69ed0ee630 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-0uy0-5910000000-ee816015eec26c8621b1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive splash10-0udi-0009000000-ec1cab852ed9f9f78fa4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-0udi-1907000000-6f36df2733dadae380c2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-0udi-0309000000-976a99c106ceca16d73b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-0pi0-1900000000-b2e286366d41e47dd8fc View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-0udi-0209000000-e891863ec110aeb660b0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-0udi-0940000000-aa52db00c1defe3ccf75 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-0udi-0219000000-5ef285c4b6bfd220b8b1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-0udi-0219000000-547c83bb70e7da007d6c View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-0udi-1907000000-a59602c09f66e9656068 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive splash10-0udi-0009000000-4416f39adf6c9b919bfa View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative splash10-0udi-0019000000-eb14ec62fc2fb2f1da88 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative splash10-0ufr-0910000000-0730bca525c17aac75c5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - ESI-TOF 10V, Negative splash10-004i-0030290000-06238e4a98a4daad3265 View in MoNA LC-MS/MS LC-MS/MS Spectrum - ESI-TOF , Negative splash10-0udi-0039008002-9df3edfb34deb15f8474 View in MoNA LC-MS/MS LC-MS/MS Spectrum - ESI-TOF 10V, Negative splash10-0udi-0039008002-9df3edfb34deb15f8474 View in MoNA LC-MS/MS LC-MS/MS Spectrum - ESI-TOF 20V, Negative splash10-0uka-0193000000-3325ca1a080730a9c0bf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udi-0019000000-ee8570ac70818e8939bb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udi-0279000000-71b5db7ef8322cc8b9e9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0zg0-7960000000-7edbb229853a642749ac View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-0009000000-21580b9d8394d2eea3a5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0udi-0239000000-b77fcb9c0ce11dc515bf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0apr-5940000000-0590bdee504c5ed6ba36 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Perez-Vizcaino F, Duarte J, Andriantsitohaina R: Endothelial function and cardiovascular disease: effects of quercetin and wine polyphenols. Free Radic Res. 2006 Oct;40(10):1054-65. Pubmed: 17015250
Synthesis Reference:	Krewson, Charles F. Colloidal flavonols. (1953), US 2637725 19530505 CAN 47:42700 AN 1953:42700
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 16243 HMDB ID HMDB05794 Pubchem Compound ID 5280343 Kegg ID C00389 ChemSpider ID 4444051 Wikipedia Quercetin BioCyc ID 3457-TETRAHYDROXY-3-METHOXYFLAVONE EcoCyc ID 3457-TETRAHYDROXY-3-METHOXYFLAVONE Ligand Expo QUE