2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one dihydrate

• ChemBase ID: 72973
• Molecular Formular: C15H14O9
• Molecular Mass: 338.26626
• Monoisotopic Mass: 338.06378203
• SMILES: c1(cc(c2c(c1)oc(c(c2=O)O)c1ccc(c(c1)O)O)O)O.O.O
• Canonical SMILES: Oc1cc(O)c2c(c1)oc(c(c2=O)O)c1ccc(c(c1)O)O.O.O
• InChI: InChI=1S/C15H10O7.2H2O/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;2*1H2
• InChIKey: GMGIWEZSKCNYSW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one dihydrate
• IUPAC Traditional name: quercetin dihydrate
• Synonyms: Sophoretin; Meletin; Quercetine; Xanthaurine; Quercetol; Quercitin; Quercetin dihydrate; 3,3′,4′,5,7-Pentahydroxyflavone dihydrate; QUERCITRIN DIHYDRATE; Quercetin dihydrate; 3,3',4',5,7-Pentahydroxyflavone dihydrate; 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one dihydrate; QUERCETIN; 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one dihydrate; Quercetin dihydrate; 3,3',4',5,7-Pentahydroxyflavone dihydrate; Quercetin hydrate; 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one dihydrate; 2-(3,4-二羟苯基)-3,5,7-三羟基-4H-1-苯并吡喃-4-酮 二水合物; 3,3′,4′,5,7-五羟基黄酮 二水合物; 槲皮素 二水合物; 栎精二水合物

Database IDs

• CAS Number: 6151-25-3
• EC Number: 204-187-1
• MDL Number: MFCD00149487
• Beilstein Number: 317313
• Merck Index: 148034
• PubChem SID: 162037893; 24278668
• PubChem CID: 5284452
• Color Index Number: 75670

CALCULATED PROPERTIES

• Acid pKa: 6.3790317
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 2.1026077
• LogD (pH = 7.4): 1.000175
• Log P: 2.1562994
• Molar Refractivity: 76.8622 cm^3
• Polarizability: 28.418238 Å^3
• Polar Surface Area: 127.45 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M NaOH: soluble50 mg/mL; DMSO; Methanol
• Apperance: yellow powder; Yellow Solid
• Melting Point: > 300°C; >270°C (dec.); >300 °C(lit.); 310-315°C; 315(dec.)°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer; 2-8°C
• Storage Warning: Toxic
• RTECS: LK8950000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 25; 25-68; R:25
• Safety Statements: 20-36/37-45-60; 45; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301; H301-H341
• GHS Precautionary statements: P281-P301+P310-P321-P308+P313-P405-P501A; P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥98% (HPLC); 95+%; 97%
• Grade: primary reference standard
• Salt Data: ihydrate
• Empirical Formula (Hill Notation): C15H10O7 · 2H2O

DETAILS

MP Biomedicals - 02152003

Dihydrate
Crystalline
Inhibitor of protein tyrosine kinases.

MP Biomedicals - 05203879

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2347

Research Area: Inflammation
Biological Activity:
Quercetin (Sophoretin) is a PI3K and PKC inhibitor with IC50 of 3.8 μM and 15µg/ml. It strongly abrogated PI3K and Src kinases, mildly inhibited Akt1/2, and slightly affected PKC, p38 and ERK1/2. [1][2] Quercetin is a naturally-occurring polar auxin transport inhibitor with IC50 of 0.8, 16.7, 6.1, 11.36 µM for the inhibition of LDH% release, the inhibition of TNF-induced PMN-EC adhesion, TNF-induced inhibition of DNA synthesis and proliferation. It is a type of plant-based chemical, or phytochemical, known as a flavonol and a plant-derived flavonoid found in fruits, vegetables, leaves and grains. It also may be used as an ingredient in supplements, beverages or foods. In several studies, it may have anti-inflammatory and antioxidant properties, and it is being investigated for a wide range of potential health benefits. [3]References on Quercetin (Sophoretin)[1] Mol Pharmacol, 2001, 59:1138–1146[2] Fitoterapia, 2010, 81:75–80

Sigma Aldrich - Q0125

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
槲皮素二水合物是具有抗癌活性的黄酮类化合物。槲皮素为线粒体 ATP 酶和磷酸二酯酶抑制剂。它可抑制 PI3 激酶活性并且轻微抑制 PIP 激酶活性。槲皮素对癌细胞系具有抗增殖作用，通过 II 型雌激素受体降低癌细胞的生长，并且阻滞细胞周期晚期 G1 相中人类白血病 T 细胞。

Sigma Aldrich - 00200595

Application
Reference standard in the analysis of herbal medicinal products.
General description
Produced and qualified by HWI AnalytikExact content by quantitative NMR can be found on the certificate
Biochem/physiol Actions
Quercetin dihydrate 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.

Toronto Research Chemicals - Q509500

A flavonoid with anticancer activity. It 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 cel

REFERENCES

• http://www.drugbank.ca/drugs/DB04216
• Graziani, Y. et al.: J. Biochem., 135, 583 (1983)
• Levy, J. et al.: Biochem. Biophys. Res. Comm., 123, 1227 (1983)
• Wei, Y.Q. et al.: Cancer Res., 54, 4952 (1983)