Q4951

Quercetin

≥95% (HPLC), solid, anticancer agent

• Synonym(s): 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one, 3,3′,4′,5,6-Pentahydroxyflavone
• Empirical Formula (Hill Notation): C₁₅H₁₀O₇
• CAS Number: 117-39-5
• Molecular Weight: 302.24
• Beilstein: 317313
• EC Number: 204-187-1
• UNSPSC Code: 12352207
• PubChem Substance ID: 329823865
• NACRES: NA.77

Properties

• Product Name: Quercetin, ≥95% (HPLC), solid
• biological source: synthetic (organic)
• Quality Level: 200
• Assay: ≥95% (HPLC)
• form: solid
• mp: 316.5 °C
• solubility: water: practically insoluble
• storage temp.: room temp
• SMILES string: OC1=CC(O)=C2C(OC(C3=CC=C(O)C(O)=C3)=C(O)C2=O)=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
• InChI key: REFJWTPEDVJJIY-UHFFFAOYSA-N

Description

General description

Quercetin is a polyphenolic flavonoid, found in food including onions, asparagus, buckwheat, radish leaves, green tea, cranberry, broccoli, apple, blueberry, and coriander. Quercetin shows strong intramolecular H-binding, which contributes to the bioavailability and transport of the compound. This explains the biological multi-functional nature of the compound and allows for the formation of strong complexes, frequently with metals.[1] Quercetin inhibits cellular proliferation and minimizes DNA damage. Among its many cardiovascular protection properties, quercetin has antioxidant and antiplatelet properties as well as antiplatelet and anti-muscle cell proliferation and migration. It also enhances cardiac cell mitochondrial function and inhibits NF-κB. Numerous animal studies involving dietary quercetin supplementation have shown a protective effect against cardiac problems.[2]

Application

• Quercetin has been used as an antioxidant which reversed the immunosuppressive effects of high glucose and hyperglycemic sera in type 2 diabetic patients.[3]
• It has been used as a detoxifying phytochemical in Apis mellifera.[4]
• It has been used as a positive control in DPPH (2,2- diphenyl-1-picryhydrazyl) radical scavenging assay. It has also been used for the preparation of calibration curve to determine total flavonoid content.[5]

Biochem/physiol Actions

Quercetin is a flavonoid with anticancer activity. Quercetin is a mitochondrial ATPase and phosphodiesterase inhibitor. It Inhibits PI3-kinase activity and slightly inhibits PIP kinase activity. Quercetin has antiproliferative effects on cancer cell lines, reduces cancer cell growth via type II estrogen receptors, and arrests human leukemic T cells in late G1 phase of the cell cycle. Quercetin may also inhibit fatty acid synthase activity.

Features and Benefits

This compound is a featured product for ADME Tox and Kinase Phosphatase research. Discover more featured ADME Tox and Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Dopamine and Norepinephrine Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

This chemical is soluble in DMSO (30 mg/ml), DMF (~30 mg/ml), and ethanol (~2 mg/ml).

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves