All Photos(3)

Documents

Q4951

Quercetin

Name: Quercetin
Brand: SIGMA

≥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

Sign Into View Organizational & Contract Pricing

All Photos(3)

About This Item

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

product name

Quercetin, ≥95% (HPLC), solid

biological source

synthetic (organic)

Quality Level

100

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

Looking for similar products? Visit Product Comparison Guide

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. 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.

Application

Quercetin has been used as an antioxidant which reversed the immunosuppressive effects of high glucose and hyperglycemic sera in type 2 diabetic patients.
It has been used as a detoxifying phytochemical in Apis mellifera.
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.

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).

Pictograms

GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Quercetin treatment reduces the severity of renal dysplasia in a beta-catenin dependent manner.

Joanna Cunanan et al.

PloS one, 15(6), e0234375-e0234375 (2020-06-20)

Renal dysplasia, the major cause of childhood renal failure, is characterized by defective branching morphogenesis and nephrogenesis. Beta-catenin, a transcription factor and cell adhesion molecule, is markedly increased in the nucleus of kidney cells in human renal dysplasia and contributes

Exhausted Woods from Tannin Extraction as an Unexplored Waste Biomass: Evaluation of the Antioxidant and Pollutant Adsorption Properties and Activating Effects of Hydrolytic Treatments.

Lucia Panzella et al.

Antioxidants (Basel, Switzerland), 8(4) (2019-04-04)

Exhausted woods represent a byproduct of tannin industrial production processes and their possible exploitation as a source of antioxidant compounds has remained virtually unexplored. We herein report the characterization of the antioxidant and other properties of practical interest of exhausted

Phenolic and flavonoid content and antioxidants capacity of pressurized liquid extraction and perculation method from roots of Scutellaria pinnatifida A. Hamilt. subsp alpina (Bornm) Rech. f.

Golmakani E et al.

Journal of Supercritical Fluids, 95, 318-324 (2014)

High glucose and hyperglycemic sera from type 2 diabetic patients impair DC differentiation by inducing ROS and activating Wnt/?-catenin and p38 MAPK.

Gilardini Montani MS et al.

Biochimica et Biophysica Acta, 1862, 805-805 (2016)

Specific localization of quercetin-3-O-glucuronide in human brain.

Akari Ishisaka et al.

Archives of biochemistry and biophysics, 557, 11-17 (2014-06-04)

In recent years, many papers have suggested that dietary flavonoids may exert beneficial effects in the brain tissue for the protection of neurons against oxidative stress and inflammation. However, the bioavailability of flavonoids across the blood-brain barrier and the localization

View All Related Papers

Articles

Fatty Acid Synthesis in Cancer Cells

Fatty acid synthesis supports cancer cell proliferation, essential for membrane generation, protein modification, and bioenergetics.

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

Discover Bioactive Small Molecules for ADME/Tox

Discover Bioactive Small Molecules for Lipid Signaling Research

Protocols

HPLC Analysis of Flavonoids on Ascentis® RP-Amide

Protocol for HPLC Analysis of Flavonoids on Ascentis® RP-Amide

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service