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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2007-01-22 21:47:08 UTC |
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Update Date | 2019-01-11 19:18:56 UTC |
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HMDB ID | HMDB0005794 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Quercetin |
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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. Quercetin itself (aglycone quercetin), 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. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an 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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Structure | |
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Synonyms | Value | Source |
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2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one | ChEBI | 3,3',4',5,7-Pentahydroxyflavone | ChEBI | 3,5,7,3',4'-Pentahydroxyflavone | ChEBI | Sophoretin | ChEBI | Xanthaurine | ChEBI | 2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chromen-4-one | HMDB | 3',4',5,7-Tetrahydroxyflavan-3-ol | HMDB | 3',4',5,7-Tetrahydroxyflavon-3-ol | HMDB | 3,4',5,5',7-Pentahydroxy-flavone | HMDB | 3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-ON | HMDB | Flavin meletin | HMDB | Meletin | HMDB | Quercetin dihydrate | HMDB | Quercetol | HMDB | Quertin | HMDB | Dikvertin | MeSH |
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Chemical Formula | C15H10O7 |
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Average Molecular Weight | 302.2357 |
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Monoisotopic Molecular Weight | 302.042652674 |
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IUPAC Name | 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one |
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Traditional Name | quercetin |
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CAS Registry Number | 117-39-5 |
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SMILES | OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1 |
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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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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as flavonols. These 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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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 316 - 318 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.06 mg/mL at 16 °C | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (5 TMS) | splash10-0bt9-2611390000-f8e98c928a7ed82acda4 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0bt9-2611390000-f8e98c928a7ed82acda4 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0079-0591000000-2a146657da898ec9322e | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive | splash10-00l2-2093078000-1de46637305246feffd2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-0009000000-d4689b76f41c73487399 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0udi-0967000000-613e61ec0c69ed0ee630 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0uy0-5910000000-ee816015eec26c8621b1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive | splash10-0udi-0009000000-ec1cab852ed9f9f78fa4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0udi-1907000000-6f36df2733dadae380c2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0udi-0309000000-976a99c106ceca16d73b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0pi0-1900000000-b2e286366d41e47dd8fc | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0udi-0209000000-e891863ec110aeb660b0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-0940000000-aa52db00c1defe3ccf75 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-0219000000-5ef285c4b6bfd220b8b1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-0219000000-547c83bb70e7da007d6c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0udi-1907000000-a59602c09f66e9656068 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive | splash10-0udi-0009000000-4416f39adf6c9b919bfa | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative | splash10-0udi-0019000000-eb14ec62fc2fb2f1da88 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative | splash10-0ufr-0910000000-0730bca525c17aac75c5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0030290000-06238e4a98a4daad3265 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0udi-0039008002-9df3edfb34deb15f8474 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0udi-0039008002-9df3edfb34deb15f8474 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0uka-0193000000-3325ca1a080730a9c0bf | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0019000000-ee8570ac70818e8939bb | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0279000000-71b5db7ef8322cc8b9e9 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zg0-7960000000-7edbb229853a642749ac | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0009000000-21580b9d8394d2eea3a5 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0239000000-b77fcb9c0ce11dc515bf | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0apr-5940000000-0590bdee504c5ed6ba36 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.0229 +/- 0.0166 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 0.0723 +/- 0.0810 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.0802 +/- 0.0817 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0-0.255 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.03 +/- 0.015 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.06 +/- 0.03 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0135 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0133 +/- 0.00730 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0400 +/- 0.0400 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0467 +/- 0.0333 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.02666 +/- 0.01333 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Detected and Quantified | 0.0065 +/- 0.013 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 291 | | details | Urine | Detected and Quantified | 0.034 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0110-0.248 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected and Quantified | 0.0037 +/- 0.0016 umol/mmol creatinine | Adult (>18 years old) | Both | Non-insulin dependent diabetes | | details | Urine | Detected and Quantified | 0.057 +/- 0.017 umol/mmol creatinine | Adult (>18 years old) | Both | Diabetes mellitus type 2 | | details |
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Associated Disorders and Diseases |
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Disease References | Diabetes mellitus type 2 |
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- Noroozi M, Burns J, Crozier A, Kelly IE, Lean ME: Prediction of dietary flavonol consumption from fasting plasma concentration or urinary excretion. Eur J Clin Nutr. 2000 Feb;54(2):143-9. [PubMed:10694785 ]
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Associated OMIM IDs | - 125853 (Diabetes mellitus type 2)
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External Links |
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DrugBank ID | DB04216 |
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Phenol Explorer Compound ID | 291 |
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FoodDB ID | FDB011904 |
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KNApSAcK ID | C00004631 |
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Chemspider ID | 4444051 |
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KEGG Compound ID | C00389 |
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BioCyc ID | CPD-520 |
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BiGG ID | Not Available |
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Wikipedia Link | Quercetin |
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METLIN ID | Not Available |
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PubChem Compound | 5280343 |
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PDB ID | QUE |
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ChEBI ID | 16243 |
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References |
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Synthesis Reference | Krewson, Charles F. Colloidal flavonols. (1953), US 2637725 19530505 CAN 47:42700 AN 1953:42700 |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General 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 ]
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