1247-97-8

Basic information

• Product Name: QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER
• Synonyms: 3,5,7,3',4'-PENTAMETHOXYFLAVONE;QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER;QUERCETIN-3,5,7,3',4';Pentamethoxyquercetin;QUERCETINPENTAMETHYLETHER;PENTAMETHYLQUERCETIN;2-(3,4-Dimethoxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one;3,3',4',5,7-Pentamethoxyflavone
• CAS NO: 1247-97-8
• Molecular Formula: C₂₀H₂₀O₇
• Molecular Weight: 372.37
• Mol File: 1247-97-8.mol
• Article Data: 37

Chemical Properties

• Melting Point: 152-156°C
• Boiling Point: 561.9 °C at 760 mmHg
• Flash Point: 246.9 °C
• Appearance: /
• Density: 1.29 g/cm³
• CAS DataBase Reference: QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER(1247-97-8)
• EPA Substance Registry System: QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER(1247-97-8)

Safety Data

• Hazardous Substances Data: 1247-97-8(Hazardous Substances Data)

Usage

Description

QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER is a chemical compound derived from quercetin, a plant flavonoid known for its antioxidant and anti-inflammatory properties. This derivative is characterized by the addition of five methyl groups to the quercetin molecule, which enhances its stability and potentially its bioavailability. This modification may also influence its biological activity and pharmacokinetics, making QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER a subject of interest for its potential therapeutic effects, including anti-cancer, anti-viral, and neuroprotective properties.

Uses

Used in Pharmaceutical Industry:
QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER is used as a potential therapeutic agent for its anti-cancer properties, where it may contribute to the inhibition of tumor growth and the modulation of various oncological signaling pathways. Its enhanced stability and bioavailability compared to the parent compound, quercetin, make it a promising candidate for further research and pharmaceutical development.
Used in Antiviral Applications:
In the field of virology, QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER is used as an antiviral agent, leveraging its ability to interfere with viral replication and pathogenesis, offering a potential strategy for the treatment of viral infections.
Used in Neuroprotective Therapies:
QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER is utilized as a neuroprotective agent, given its potential to shield the nervous system from damage and degeneration, which is particularly relevant in the context of neurodegenerative diseases.
Each of these applications underscores the versatility and potential of QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER in various medical and health-related fields, warranting continued investigation into its mechanisms of action and therapeutic potential.

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 855-97-0 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 
• 29080-58-8 5-hydroxy-3',4',7-trimethoxyflavone 
• 76650-20-9 1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone 
• 114021-60-2 2'-hydroxy-3,4,4',6'-tetramethoxychalcone 
• 1244-78-6 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone 
• 77-78-1 dimethyl sulfate 
• 117-39-5 quercetol 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 4382-17-6 3,3'-di-O-methylquercetin 
• 1245-15-4 retusin 
• 17874-42-9 2'-hydroxy-2,4',6'-trimethoxyacetophenone 
• 1385652-00-5 C₂₀H₂₂O₈ 

Downstream Products

• 1245-15-4 retusin 
• 7380-44-1 5,8-dihydroxy-3,7-dimethoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone 
• 14965-12-9 2-(3,4-dimethoxy-phenyl)-5-hydroxy-3,7,8-trimethoxy-chromen-4-one 
• 7741-47-1 hexa-O-methylogossypetin 
• 66312-97-8 3,5,7,3',4'-pentamethoxyflav-2-enol 
• 47492-60-4 3,5,7,3',4'-penta-O-methylcyanidin 
• 16820-97-6 3,5,7,3',4'-pentamethoxyflav-3-enol 
• 17277-00-8 3',4',5,7-tetra-O-methyl-α-photomethylquercetin 
• 2746-94-3 2,3,8,10-tetramethoxy<1>benzopyrano<3,2-c>benzopyran-7(5H)-one 
• 1244-78-6 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone 

Relevant articles and documents

O-ALKYLATION DE LA QUERCETINE ET SYNTHESE DE LA TETRA-O-EHYL-3,7,3',4' O-ETHYL -5 QUERCETINE

An efficient procedure is described for alkylation of quercetin with alkyl halides by use of tetraethylammonium fluoride in DMF or HMPT.The method is applied successfully to the preparation of 3,7,3',4', tetra-O-ethyl 5 O-ethylquercetin with a specific radioactivity of 45 Ci/mmol.

A flavonol glycoside-lignan ester and accompanying acylated glucosides from Monochaetum multiflorum

Four acylated glycosides along with six known glycosides were isolated from the leaves of Monochaetum multiflorum. The new compounds were characterized as 4.0-(6′-O-galloyl- β- glucopyranosyl)-cis-p-coumaric acid, 6′-O- galloylprunasin, benzyl 6′-O-galloyl-β-glucopyranoside, and a novel diester of tetrahydroxy-μ-truxinic acid with 2 mol of hyperin (monochaetin), based on NMR and MS spectral data and chemical evidence.

Method of producing an alkoxyflavone derivative

A method of producing an alkoxyflavone derivative involves a step of reacting hydroxyflavone derivative which is shown in the below chemical formula and dialkyl sulfate in the presence of dimethyl sulfoxide and an alkali hydroxide. Further, in the chemical formula below, R11-R14, R21-R25 and R3 are independently one of hydrogen, hydroxyl group, ester group, alkoxy group, alkylenedioxy group, sulfonyl group and alkyl group, respectively. However, at least two of R21-R25 and R3 are hydroxyl groups.

Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors

The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC50 of 72 ± 2 nM and its 8-C-glucoside orientin with an IC50 of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 ? resolution and quambalarine B at 2.5 ? resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.

A simple and effective preparation of quercetin pentamethyl ether from quercetin

Among the five hydroxy (OH) groups of quercetin (3,5,7,3',4'-pentahydroxyflavone), the OH group at 5 position is the most resistant to methylation due to its strong intramolecular hydrogen bonding with the carbonyl group at 4 position. Thus, it is generally difficult to synthesize the pentamethyl ether efficiently by conventional methylation. Here, we describe a simple and effective perO-methylation of quercetin with dimethyl sulfate in potassium (or sodium) hydroxide/dimethyl sulfoxide at room temperature for about 2 hours, affording quercetin pentamethyl ether (QPE) quantitatively as a single product. When methyl iodide was used in place of dimethyl sulfate, the C-methylation product 6-methylquercetin pentamethyl ether was also formed. A computational study provided a rationale for the experimental results.