Quercetin pentaacetate
Quercetin acetate · Pentaacetylquercetin · Quercetine pentaacetate · 3,3',4',5,7-Pentaacetoxyflavone · 3,3',4',5,7-Penta(acetyloxy)flavone · Quercetin pentaacetate, 10 mM in DMSO · 3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one · 2-(3,4-diacetoxyphenyl)-4-oxo-4H-chromene-3,5,7-triyl triacetate
Identifikatoren & physikalische Daten
| CAS No. | 1064-06-8 |
|---|---|
| Summenformel | C25H20O12 |
| Durchschnittliche Molmasse | 512,4 g/mol |
| Monoisotopische Masse | 512,09547607 g/mol |
| SMILES | CC(=O)Oc1cc(OC(C)=O)c2c(=O)c(OC(C)=O)c(-c3ccc(OC(C)=O)c(OC(C)=O)c3)oc2c1 |
| InChIKey | JQUHMSXLZZWRHU-UHFFFAOYSA-N |
| PubChem CID | 14005 |
| ChEMBL | CHEMBL19074 |
| DTXSID | DTXSID30147593 |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 158 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 12 |
| Frei drehbare Bindungen | 11 |
| Schwere Atome | 37 |
| Formalladung | 0 |
| Komplexität | 998 |
| Schmelzpunkt | 193 °C |
| Siedepunkt | 666.4±55.0 °C(Predicted) |
| Dichte | 1.45±0.1 g/cm3(Predicted) |
| Lagerbedingungen | Store at -20°C |
| Löslichkeit | Dichloromethane, Ethyl Acetate |
| Aggregatzustand | Solid |
| Farbe | Beige |
Anwendungen & Verwendung
Beschreibung
Pentaacetylquercetin is a pentaacetylated derivative of the flavonoid quercetin that has diverse biological activities, including antioxidant, anti-inflammatory, and anticancer properties. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in vitro (IC50 = 3.74 μg/ml) and inhibits iron(II) chloride-induced lipid peroxidation in rat liver mitochondria (IC50 = 20.2 μg/ml). Pentaacetylquercetin inhibits LPS-induced increases in nitrite (IC50 = 8.7 μM) and PGE2 production, as well as inducible nitric oxide synthase (iNOS) and COX-2 levels, in RAW 264.7 cells when used at concentrations of 20 and 40 μM. It also inhibits the growth of HL-60, U937, and SK-MEL-1 cells (IC50s = 38, 25, and 58 μM, respectively).
Verwenden
[5,7-Diacetyloxy-2-(3,4-diacetyloxyphenyl)-4-oxochromen-3-yl] Acetate is an intermediate in the synthesis of Quercetin Dihydrate (Q509500), which is a lavonoid 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 cell growth via type II estrogen receptors, and arrests human leukemic T cells in late G1 phase of the cell cycle.