Show more...Show more...Show more...
Record Information
Version2.0
Created at2007-01-22 21:47:08 UTC
Updated at2025-02-11 15:42:32 UTC
NP-MRD IDNP0001060
Natural Product DOIhttps://doi.org/10.57994/0683
Secondary Accession NumbersNone
Natural Product Identification
Common NameQuercetin
DescriptionQuercetin 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. Quercetin 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 ).
Structure
Thumb
Synonyms
Chemical FormulaC15H10O7
Average Mass302.2357 Da
Monoisotopic Mass302.04265 Da
IUPAC Name2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
Traditional Namequercetin
CAS Registry Number117-39-5
SMILES
OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)=C1
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
InChI KeyREFJWTPEDVJJIY-UHFFFAOYSA-N
Experimental Spectra
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-16View Spectrum
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Mucor hiemalisKNApSAcK Database
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.
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point316 - 318 °CNot Available
Boiling Point642.00 to 643.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.06 mg/mL at 16 °CNot Available
LogP1.989 (est)The Good Scents Company Information System
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
HMDB IDHMDB0005794
DrugBank IDDB04216
Phenol Explorer Compound ID291
FoodDB IDFDB011904
KNApSAcK IDC00004631
Chemspider ID4444051
KEGG Compound IDC00389
BioCyc IDCPD-520
BiGG IDNot Available
Wikipedia LinkQuercetin
METLIN IDNot Available
PubChem Compound5280343
PDB IDQUE
ChEBI ID16243
Good Scents IDrw1343701
References
General References
  1. 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 ]
  2. Mennen LI, Sapinho D, Ito H, Galan P, Hercberg S, Scalbert A: Urinary excretion of 13 dietary flavonoids and phenolic acids in free-living healthy subjects - variability and possible use as biomarkers of polyphenol intake. Eur J Clin Nutr. 2008 Apr;62(4):519-25. doi: 10.1038/sj.ejcn.1602744. Epub 2007 Apr 4. [PubMed:17426744 ]
  3. Morales AI, Vicente-Sanchez C, Jerkic M, Santiago JM, Sanchez-Gonzalez PD, Perez-Barriocanal F, Lopez-Novoa JM: Effect of quercetin on metallothionein, nitric oxide synthases and cyclooxygenase-2 expression on experimental chronic cadmium nephrotoxicity in rats. Toxicol Appl Pharmacol. 2006 Jan 1;210(1-2):128-35. doi: 10.1016/j.taap.2005.09.006. Epub 2005 Oct 14. [PubMed:16226777 ]
  4. Davalos A, Castilla P, Gomez-Cordoves C, Bartolome B: Quercetin is bioavailable from a single ingestion of grape juice. Int J Food Sci Nutr. 2006 Aug-Sep;57(5-6):391-8. doi: 10.1080/09637480600858662. [PubMed:17135030 ]
  5. Loke WM, Proudfoot JM, Stewart S, McKinley AJ, Needs PW, Kroon PA, Hodgson JM, Croft KD: Metabolic transformation has a profound effect on anti-inflammatory activity of flavonoids such as quercetin: lack of association between antioxidant and lipoxygenase inhibitory activity. Biochem Pharmacol. 2008 Mar 1;75(5):1045-53. doi: 10.1016/j.bcp.2007.11.002. Epub 2007 Nov 12. [PubMed:18096136 ]