1064-06-8

Usage

Uses

Used in Anticancer Applications:
QUERCETINPENTAACETATE is used as an anticancer agent for its antiproliferative effects on cancer cell lines. It reduces cancer cell growth via type II estrogen receptors and arrests human leukemic T cells in the late G1 phase of the cell cycle.
Used in Pharmaceutical Industry:
QUERCETINPENTAACETATE is used as an intermediate in the synthesis of Quercetin Dihydrate (Q509500), which is a flavonoid with anticancer activity. It serves as a mitochondrial ATPase and phosphodiesterase inhibitor, inhibiting PI3-kinase activity and slightly inhibiting PIP kinase activity.
Used in Drug Delivery Systems:
In the development of novel drug delivery systems, QUERCETINPENTAACETATE can be employed to enhance the applications and efficacy against cancer cells. It can be incorporated into various organic and metallic nanoparticles as carriers for improved delivery, bioavailability, and therapeutic outcomes.
Used in Antioxidant Applications:
QUERCETINPENTAACETATE is used as an antioxidant for its ability to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals in vitro, providing protection against oxidative stress and potential damage to cells and tissues.
Used in Anti-inflammatory Applications:
QUERCETINPENTAACETATE is used as an anti-inflammatory agent due to its capacity to inhibit LPS-induced increases in nitrite and PGE2 production, as well as inducible nitric oxide synthase (iNOS) and COX-2 levels in RAW 264.7 cells.

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

Downstream Products

• 143631-95-2 acetic acid 2-acetoxy-4-(3,5-diacetoxy-7-hydroxy-4-oxo-4H-chromen-2-yl)-phenyl ester 
• 491-50-9 quercetin 7-O-β-D-glucopyranoside 
• 602329-62-4 3,3',4',5-tetra-O-acetylquercetin 7-O-2'',3'',4'',6''-tetra-O-benzoyl-β-D-glucopyranoside 
• 103568-84-9 2-(3-acetoxy-4-benzyloxy-phenyl)-3,5,7-tris-benzyloxy-chromen-4-one 
• 1144104-71-1 C₂₆H₂₂O₁₃ 
• 19159-09-2 4-(3,5-diacetoxy-7-(2-ethoxy-2-oxoethoxy)-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate 
• 1486-63-1 3,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]-5-hydroxy-4H-1-benzopyran-4-one 
• 78386-01-3 2-(3-acetoxy-4-(benzyloxy) phenyl)-7-(benzyloxy)-4-oxo-4H-chromene-3,5-diyl diacetate 
• 482-35-9 isoquercetin 
• 6743-87-9 4',7-di-O-benzyl-3-O-(β-D-glucopyranosyl)quercetin 
• 131021-81-3 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol 
• 1610737-72-8 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-morpholino-4H-chromen-4-one 
• 1610737-83-1 4-(3,5-diacetoxy-4-oxo-7-(tosyloxy)-4H-chromen-2-yl)-1,2-phenylenediacetate 
• 1610737-87-5 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl-4-methylbenzenesulfonate 

Relevant academic research and scientific papers

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.

Isolation of arginase inhibitors from the bioactivity-guided fractionation of Byrsonima coccolobifolia leaves and stems

Byrsonima coccolobifolia leaf and stem extracts were studied in the search for possible leishmanicidal compounds using arginase (ARG) from Leishmania amazonensis as a molecular target. Flavonoids 1b, 1e-1g, 2a, 2b, and 2d-2f showed significant inhibitory

STRUCTURAL ASPECTS OF ANTHOCYANIN-FLAVONOID COMPLEX FORMATION AND ITS ROLE IN PLANT COLOR

Key Word Index - Anthocyanin; flavonoid glycosides; synthesis; complex formation; plant color; spectral properties. The complex formation of flavonoids with anthocyanins, resulting in increase in both absorbance and in a bathochromic shift of the visible absorption maximum of the latter, is based mainly on hydrogen bond formation between the carbonyl group of the anthocyanin anhydrobase and aromatic hydroxyl groups of the complex-forming flavonoids.The larger the number of hydroxyl groups in the flavonoid molecule, the strongr the complex formation.The presence of a 3-hydroxyl group in the flavonoid molecule has little effect on the complex-forming ability.The nature of the sugar substituent of the complex-forming flavonoid compound has no influence on the reaction.The 5-hydroxyl group of flavonoids is strongly bound by intramolecular hydrogen bond to the 4-carbonyl and does not participate in the complex formation.The most important hydroxyl group in the flavonoid molecule is one in the 7-position.Unsaturation at C2-C3 in the heterocyclic ring is an important factor for complex formation.Aromatic hydroxyl groups in the flavonoid system alone cannot account for all the complex-forming ability, suggesting additional involvment by electrostatic forces and configurational or steric effects.

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

Comparison of the prevention of aflatoxin B1-induced genotoxicity by quercetin and quercetin pentaacetate

Earlier work carried out in our laboratory highlighted the mode of action of acetoxy 4-methylcoumarins in preventing the genotoxicity of aflatoxin B1 (AFB1). We have in this report extended the observations to quercetin pentaacetate

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.

Ester-based precursors to increase the bioavailability of quercetin

Plant polyphenols exhibit a variety of potentially useful biochemical properties in vitro, but their evaluation and clinical exploitation in vivo is hampered by their limited bioavailability. Precursors exhibiting resistance to phase II metabolism during absorption are therefore desirable. We report here the synthesis as well as stability and solubility studies of several ester derivatives of quercetin (3,3′,4′,5,7-pentahydroxy flavone), most of which comprise an aminoacyl group. To model transepithelial absorption, we tested transport across supported tight monolayers of MDCK-1, MDCK-2, and Caco-2 cells. Quercetin itself was extensively conjugated by all three types of cells. A few of our precursors did not cross the monolayers, but others did, undergoing partial deacylation, No phase II conjugation was observed during transport of these compounds across MDCK or some Caco-2 clones. With other Caco-2 lines complete deacylation occurred, followed by metabolism of quercetin. Since elimination of residual acyl groups is expected to take place in vivo, ester derivatives of polyphenols may constitute a useful method to increase systemic aglycone concentrations.

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

Binding investigation between M2-1protein from hRSV and acetylated quercetin derivatives: 1H NMR, fluorescence spectroscopy, and molecular docking

The human Respiratory Syncytial Virus (hRSV) is the main responsible for occurrences of respiratory diseases as pneumonia and bronchiolitis in children and elderly. M2-1 protein from hRSV is an important antitermination factor for transcription process that prevents the premature dissociation of the polymerase complex, making it a potential target for developing of inhibitors of the viral replication. The present study reports the interaction of the M2-1 tetramer with pera (Q1) and tetracetylated (Q2) quercetin derivatives, which were synthesized with the objective of generating stronger bioactive compounds against oxidation process. Fluorescence experiments showed binding constants of the M2-1/compounds complexes on order of 104 M? 1 with one ligand per monomeric unit, being the affinity of Q2 stronger than Q1. The thermodynamic analysis revealed values of ΔH > 0 and ΔS > 0, suggesting that hydrophobic interactions play a key role in the formation of the complexes. Molecular docking calculations indicated that binding sites for the compounds are in contact interfaces between globular and zinc finger domains of the monomers and that hydrogen bonds and stacking interactions are important contributions for stabilization of the complexes. Thus, the interaction of the acetylated quercetin derivatives in the RNA-binding sites of M2-1 makes these potential candidates for viral replication inhibitors.

Peracetylation of polyphenols under rapid and mild reaction conditions

Structural modifications are an important tool for studying the properties of naturally occurring polyphenols. Regarding the preparation of acetyl esters, the presence of hydroxyl groups stabilized by intramolecular hydrogen bonds may pose an obstacle for