1.0 2020-03-19 00:33:33 UTC 2022-12-13 19:31:28 UTC CDB000372 Quercetin 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 one of 23 flavonoids found in cannabis plants (PMID: 6991645). Quercetin is a widely distributed flavonoid found in many other 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). 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one 3,3',4',5,7-Pentahydroxyflavone 3,5,7,3',4'-Pentahydroxyflavone Sophoretin Xanthaurine 3,3',4,5,7-Pentahydroxyflavone Dikvertin 2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chromen-4-one 3',4',5,7-Tetrahydroxyflavan-3-ol 3',4',5,7-Tetrahydroxyflavon-3-ol 3,4',5,5',7-Pentahydroxy-flavone 3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-ON Flavin meletin Meletin Quercetin dihydrate Quercetol Quertin 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-benzopyran-4-one 3,3’,4’,5,7-Pentahydroxyflavone 3,5,7,3’,4’-Pentahydroxyflavone 3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one 3'-Hydroxykaempferol 3’-Hydroxykaempferol Quercetine Quertine C15H10O7 302.24 302.0427 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one quercetin 73123-10-1 OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)=C1 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 REFJWTPEDVJJIY-UHFFFAOYSA-N 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. Flavonols Organic compounds Phenylpropanoids and polyketides Flavonoids Flavones Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 3-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Benzene and substituted derivatives Catechols Chromones Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Oxacyclic compounds Polyols Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 3-hydroxyflavone 3-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Aromatic heteropolycyclic compound Benzenoid Benzopyran Catechol Chromone Heteroaromatic compound Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Polyol Pyran Pyranone Vinylogous acid 7-hydroxyflavonol Flavones and Flavonols Flavones and Flavonols flavonols pentahydroxyflavone water_solubility 0.06 mg/mL at 16 °C melting_point 316 - 318 °C logp 1.81 ALOGPS logs -3.06 ALOGPS logp 2.16 ChemAxon pka_strongest_acidic 6.38 ChemAxon pka_strongest_basic -4 ChemAxon iupac 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one ChemAxon average_mass 302.24 ChemAxon mono_mass 302.0427 ChemAxon smiles OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)=C1 ChemAxon formula C15H10O7 ChemAxon 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 ChemAxon inchikey REFJWTPEDVJJIY-UHFFFAOYSA-N ChemAxon polar_surface_area 127.45 ChemAxon refractivity 76.86 ChemAxon polarizability 28.54 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB011904 DB04216 4444051 291 C00389 C00004631 16243 5280343 QUE CPD-520 Quercetin Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Fischer C, Speth V, Fleig-Eberenz S, Neuhaus G: Induction of Zygotic Polyembryos in Wheat: Influence of Auxin Polar Transport. Plant Cell. 1997 Oct;9(10):1767-1780. doi: 10.1105/tpc.9.10.1767. 12237347 Williams RJ, Spencer JP, Rice-Evans C: Flavonoids: antioxidants or signalling molecules? Free Radic Biol Med. 2004 Apr 1;36(7):838-49. doi: 10.1016/j.freeradbiomed.2004.01.001. 15019969 Moutsatsou P: The spectrum of phytoestrogens in nature: our knowledge is expanding. Hormones (Athens). 2007 Jul-Sep;6(3):173-93. 17724002 Maggiolini M, Vivacqua A, Fasanella G, Recchia AG, Sisci D, Pezzi V, Montanaro D, Musti AM, Picard D, Ando S: The G protein-coupled receptor GPR30 mediates c-fos up-regulation by 17beta-estradiol and phytoestrogens in breast cancer cells. J Biol Chem. 2004 Jun 25;279(26):27008-16. doi: 10.1074/jbc.M403588200. Epub 2004 Apr 16. 15090535 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. doi: 10.1080/10715760600823128. 17015250