Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:53 UTC |
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Update date | 2020-09-17 15:33:11 UTC |
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Primary ID | FDB011904 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Quercetin |
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Description | Quercetin, 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). |
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CAS Number | 117-39-5 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C15H10O7 |
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IUPAC name | 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one |
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InChI Identifier | 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 |
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InChI Key | REFJWTPEDVJJIY-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1 |
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Average Molecular Weight | 302.2357 |
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Monoisotopic Molecular Weight | 302.042652674 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavones |
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Direct Parent | Flavonols |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Foods | Cocoa and cocoa products Grains: Nuts and legumes: Fruits and vegetables: Fats and oils: Beverages: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Quercetin, 5 TMS, GC-MS Spectrum | splash10-0bt9-2611390000-f8e98c928a7ed82acda4 | Spectrum | GC-MS | Quercetin, non-derivatized, GC-MS Spectrum | splash10-0bt9-2611390000-f8e98c928a7ed82acda4 | Spectrum | Predicted GC-MS | Quercetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0079-0591000000-2a146657da898ec9322e | Spectrum | Predicted GC-MS | Quercetin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00l2-2093078000-1de46637305246feffd2 | Spectrum | Predicted GC-MS | Quercetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-0009000000-d4689b76f41c73487399 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0udi-0967000000-613e61ec0c69ed0ee630 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0uy0-5910000000-ee816015eec26c8621b1 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive | splash10-0udi-0009000000-ec1cab852ed9f9f78fa4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0udi-1907000000-6f36df2733dadae380c2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0udi-0309000000-976a99c106ceca16d73b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0pi0-1900000000-b2e286366d41e47dd8fc | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0udi-0209000000-e891863ec110aeb660b0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-0940000000-aa52db00c1defe3ccf75 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-0219000000-5ef285c4b6bfd220b8b1 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-0219000000-547c83bb70e7da007d6c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0udi-1907000000-a59602c09f66e9656068 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive | splash10-0udi-0009000000-4416f39adf6c9b919bfa | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative | splash10-0udi-0019000000-eb14ec62fc2fb2f1da88 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative | splash10-0ufr-0910000000-0730bca525c17aac75c5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0030290000-06238e4a98a4daad3265 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0udi-0039008002-9df3edfb34deb15f8474 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0udi-0039008002-9df3edfb34deb15f8474 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0uka-0193000000-3325ca1a080730a9c0bf | 2017-08-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0019000000-ee8570ac70818e8939bb | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0279000000-71b5db7ef8322cc8b9e9 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zg0-7960000000-7edbb229853a642749ac | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0009000000-21580b9d8394d2eea3a5 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0239000000-b77fcb9c0ce11dc515bf | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0apr-5940000000-0590bdee504c5ed6ba36 | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 4444051 |
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ChEMBL ID | CHEMBL50 |
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KEGG Compound ID | C00389 |
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Pubchem Compound ID | 5280343 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 291 |
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DrugBank ID | DB04216 |
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HMDB ID | HMDB05794 |
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CRC / DFC (Dictionary of Food Compounds) ID | HBR39-C:HBR39-C |
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EAFUS ID | Not Available |
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Dr. Duke ID | QUERCETIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00004631 |
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HET ID | QUE |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Quercetin |
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Phenol-Explorer Metabolite ID | 291 |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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.
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