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Q4951

Sigma-Aldrich

Quercetin

≥95% (HPLC), solid

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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:
Molecular Weight:
302.24
Beilstein/REAXYS Number:
317313
EC Number:
PubChem Substance ID:

biological source

synthetic (organic)

Quality Level

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

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This Item
PHR14881592409PHL89262
Quercetin ≥95% (HPLC), solid

Q4951

Quercetin

Quercetin Pharmaceutical Secondary Standard; Certified Reference Material

PHR1488

Quercetin

Quercetin United States Pharmacopeia (USP) Reference Standard

1592409

Quercetin

Quercetin phyproof® Reference Substance

PHL89262

Quercetin

form

solid

form

-

form

-

form

-

Quality Level

100

Quality Level

300

Quality Level

-

Quality Level

-

storage temp.

room temp

storage temp.

-10 to -25°C

storage temp.

−20°C

storage temp.

-

solubility

water: practically insoluble

solubility

-

solubility

-

solubility

-

biological source

synthetic (organic)

biological source

-

biological source

-

biological source

-

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

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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Customers Also Viewed

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Quercetin, Dihydrate A cell-permeable and reversible inhibitor of PIM1 kinase (IC₅₀ = 43 nM), PI 3-K (IC₅₀ = 3.8 µM) and phospholipase A2 (IC₅₀ = 2 µM).

Millipore

551600-M

Quercetin, Dihydrate

Quercitrin primary reference standard

00740580

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Gallic acid 97.5-102.5% (titration)

Sigma-Aldrich

G7384

Gallic acid

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Sigma-Aldrich

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Rutin phyproof® Reference Substance

PHL89270

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Luteolin ≥98% (TLC), powder

Sigma-Aldrich

L9283

Luteolin

Isorhamnetin ≥95.0% (HPLC)

Sigma-Aldrich

17794

Isorhamnetin

Quercetin dihydrate phyproof® Reference Substance

PHL89263

Quercetin dihydrate

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
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)
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
Impacts of Dietary Phytochemicals in the Presence and Absence of Pesticides on Longevity of Honey Bees (Apis mellifera).
Liao LH et al.
Insects, 8, E22-E22 (2017)
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)

Articles

Information on fatty acid synthesis and metabolism in cancer cells. Learn how proliferatively active cells require fatty acids for functions such as membrane generation, protein modification, and bioenergetic requirements. These fatty acids are derived either from dietary sources or are synthesized by the cell.

Discover Bioactive Small Molecules for Lipid Signaling Research

Protocols

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

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