1064-06-8

Basic information

• Product Name: QUERCETINPENTAACETATE
• Synonyms: 3,3',4',5,7-Penta(acetyloxy)flavone;3,3',4',5,7-Pentaacetoxyflavone;Quercetin acetate;Quercetine pentaacetate;[5,7-Diacetyloxy-2-(3,4-diacetyloxyphenyl)-4-oxochromen-3-yl] Acetate
• CAS NO: 1064-06-8
• Molecular Formula: C₂₅H₂₀O₁₂
• Molecular Weight: 512.42
• Mol File: 1064-06-8.mol
• Article Data: 49

Chemical Properties

• Melting Point: 193 °C
• Boiling Point: 666.4°C at 760 mmHg
• Flash Point: 284.7°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 1.27E-17mmHg at 25°C
• Refractive Index: 1.6
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: QUERCETINPENTAACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: QUERCETINPENTAACETATE(1064-06-8)
• EPA Substance Registry System: QUERCETINPENTAACETATE(1064-06-8)

Safety Data

• Hazardous Substances Data: 1064-06-8(Hazardous Substances Data)

Usage

Description

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).

Uses

[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.

InChI:InChI=1/C25H20O12/c1-11(26)32-17-9-20(35-14(4)29)22-21(10-17)37-24(25(23(22)31)36-15(5)30)16-6-7-18(33-12(2)27)19(8-16)34-13(3)28/h6-10H,1-5H3

Upstream product

• 117-39-5 quercetol 
• 108-24-7 acetic anhydride 
• 153-18-4 rutin 
• 127-09-3 sodium acetate 
• 7251-37-8 4-(3,7-diacetoxy-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate 
• 75-36-5 acetyl chloride 

Downstream Products

• 103568-84-9 2-(3-acetoxy-4-benzyloxy-phenyl)-3,5,7-tris-benzyloxy-chromen-4-one 
• 480-19-3 isorhamnetin 
• 1144104-76-6 2-((2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl)oxy)acetic acid 
• 19159-09-2 4-(3,5-diacetoxy-7-(2-ethoxy-2-oxoethoxy)-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate 
• 143631-97-4 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-ylacetate 
• 528-48-3 3,7,3',4'-tetrahydroxyflavone 
• 114840-33-4 3,3′,4′,7-tetraacetoxyflavone 
• 7251-37-8 4-(3,7-diacetoxy-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate 
• 1610737-93-3 3,5-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-7-morpholino-4H-chromen-4-one 
• 1610737-89-7 3,5-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-oxo-4H-chromen-7-yl-4-methylbenzenesulfonate 
• 1610737-87-5 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl-4-methylbenzenesulfonate 
• 1610737-83-1 4-(3,5-diacetoxy-4-oxo-7-(tosyloxy)-4H-chromen-2-yl)-1,2-phenylenediacetate 
• 1610737-72-8 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-morpholino-4H-chromen-4-one 
• 1310686-93-1 C₂₀H₁₈O₁₀ 

Relevant articles and documents

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Quercetin derivatives as novel antihypertensive agents: Synthesis and physiological characterization

The antihypertensive flavonol quercetin (Q1) is endowed with a cardioprotective effect against myocardial ischemic damage. Q1 inhibits angiotensin converting enzyme activity, improves vascular relaxation, and decreases oxidative stress and gene expression. However, the clinical application of this flavonol is limited by its poor bioavailability and low stability in aqueous medium. In the aim to overcome these drawbacks and preserve the cardioprotective effects of quercetin, the present study reports on the preparation of five different Q1 analogs, in which all OH groups were replaced by hydrophobic functional moieties. Q1 derivatives have been synthesized by optimizing previously reported procedures and analyzed by spectroscopic analysis. The cardiovascular properties of the obtained compounds were also investigated in order to evaluate whether chemical modification affects their biological efficacy. The interaction with β-adrenergic receptors was evaluated by molecular docking and the cardiovascular efficacy was investigated on the ex vivo Langendorff perfused rat heart. Furthermore, the bioavailability and the antihypertensive properties of the most active derivative were evaluated by in vitro studies and in vivo administration (1 month) on spontaneously hypertensive rats (SHRs), respectively. Among all studied Q1 derivatives, only the ethyl derivative reduced left ventricular pressure (at 10- 8 M ÷ 10- 6 M doses) and improved relaxation and coronary dilation. NOSs inhibition by L-NAME abolished inotropism, lusitropism and coronary effects. Chronic administration of high doses of this compound on SHR reduced systolic and diastolic pressure. Differently, the acetyl derivative induced negative inotropism and lusitropism (at 10- 10 M and 10- 8 ÷ 10- 6 M doses), without affecting coronary pressure. Accordingly, docking studies suggested that these compounds bind both β1/β2-adrenergic receptors. Taking into consideration all the obtained results, the replacement of OH with ethyl groups seems to improve Q1 bioavailability and stability; therefore, the ethyl derivative could represent a good candidate for clinical use in hypertension.

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How sorbitan monostearate can increase drug-loading capacity of lipid-core polymeric nanocapsules

Lipid-core polymeric nanocapsules are innovative devices that present distinguished characteristics due to the presence of sorbitan monostearate into the oily-core. This component acted as low-molecular-mass organic gelator for the oil (medium chain trigl

Efficient acylation and one-pot synthesis of dehydroandrographolide succinate on a large scale assisted with microwave radiation

A rapid and convenient method for acylation and large-scale synthesis of dehydroandrographolide succinate has been developed under microwave irradiation. It is a one-pot condensation and is compatible with dehydration and rearrangement of double bond in mild reaction conditions with good yield, high purity (up to 99.8%), time-savings, few pollutants and low cost. In addition, a number of acylation derivatives were synthesized under microwave irradiation.

Design, synthesis and pharmacological evaluation of ester-based quercetin derivatives as selective vascular KCa1.1 channel stimulators

Quercetin represents one of the most studied dietary flavonoids; it exerts a panel of pharmacological activities particularly on the cardiovascular system. Stimulation of vascular KCa1.1 channels contributes to its vasorelaxant activity, which

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ACYLATED ACTIVE AGENTS AND METHODS OF THEIR USE FOR THE TREATMENT OF METABOLIC DISORDERS AND NONALCOHOLIC FATTY LIVER DISEASE

Disclosed herein are acylated active agents (e.g., acylated hydroxybenzoic acid), compositions containing them, unit dosage forms containing them, and methods of their use, e.g., for treating a metabolic disorder or nonalcoholic fatty liver disease or for

Extraction, Isolation and Characterization of Valuable Worked on Acacia Tortilis

Acacia tortilis is one of the important species of genus Acacia belonging to family Leguminaceae. Though there is no more study performed on this plant but it plays important role in the countries where it found. These countries include North Africa, Arabian Peninsula and Asian countries. The various part of Acacia tortilis plant say leaves, pods, gum exudates and bark were used as antidiabetic, antidiarrhoeal, antiasthmatic and also had several other medicinal benefits. The present discussion deals with the isolation and characterization of the following compounds from the leaves of Acacia tortilis. Lupan-3-ol, 12,20-diene, Lupan-12, 20-dien 3-one, Friedelin, ?-amyrin, ?- sitosterol, Apigenin, Luteolin, Quercetin, 5,7-dihydroxy-4-p-methyl benzylisoflavone, Vitexin, 2',6'-dihydroxy chalcone-4'-O-glucoside.