529-51-1

Basic information

• Product Name: 5-METHOXY-3,3',4',7-TETRAHYDROXYFLAVONE
• Synonyms: AZALEATIN;3,3',4',7-TETRAHYDROXY-5-METHOXYFLAVONE;5-METHOXY-3,3',4',7-TETRAHYDROXYFLAVONE;5-O-Methylquercetin;2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-5-methoxychromen-4-one;2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-5-Methoxy-4H-1-benzopyran-4-one;Quercetin 5-Methyl Ether;2-(3,4-Dihydroxycyclohexa-2,4-dien-1-yl)-3,7-dihydroxy-5-methoxy-4H-chromen-4-one
• CAS NO: 529-51-1
• Molecular Formula: C₁₆H₁₂O₇
• Molecular Weight: 316.26
• Product Categories: Flavanols;Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 529-51-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 322℃
• Boiling Point: 657.3 °C at 760 mmHg
• Flash Point: 250.2 °C
• Appearance: /
• Density: 1.634 g/cm³
• Vapor Pressure: 3.59E-18mmHg at 25°C
• Refractive Index: 1.74
• PKA: 6.46±0.40(Predicted)
• CAS DataBase Reference: 5-METHOXY-3,3',4',7-TETRAHYDROXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-3,3',4',7-TETRAHYDROXYFLAVONE(529-51-1)
• EPA Substance Registry System: 5-METHOXY-3,3',4',7-TETRAHYDROXYFLAVONE(529-51-1)

Safety Data

• Hazardous Substances Data: 529-51-1(Hazardous Substances Data)

Usage

Description

5-METHOXY-3,3',4',7-TETRAHYDROXYFLAVONE, also known as an O-Methylated analogue of the flavanoid Quercertin (Q509500), is a monomethoxyflavone derived from quercetin with a methoxy group replacing the hydroxy group at position 5. It is a small molecule inhibitor of the NADPH Oxidase 4 enzyme and has been studied for its potential effects on ocular blood flow and retinal function recovery.

Uses

Used in Pharmaceutical Research:
5-METHOXY-3,3',4',7-TETRAHYDROXYFLAVONE is used as a research compound for studying the structure-activity relationship of flavonoids, particularly in the context of ocular blood flow and retinal function recovery in animal models.
Used in Ophthalmology:
In the field of ophthalmology, 5-METHOXY-3,3',4',7-TETRAHYDROXYFLAVONE is used as a potential therapeutic agent for improving ocular blood flow in rabbits and promoting retinal function recovery in rat eyes, which could have implications for the treatment of various eye diseases and conditions.
Used in Enzyme Inhibition Studies:
5-METHOXY-3,3',4',7-TETRAHYDROXYFLAVONE is also used as a small molecule inhibitor of the NADPH Oxidase 4 enzyme, which plays a role in various cellular processes and diseases. Its inhibition may provide insights into the development of novel therapeutic strategies targeting this enzyme.

InChI:InChI=1/C16H12O7/c1-22-11-5-8(17)6-12-13(11)14(20)15(21)16(23-12)7-2-3-9(18)10(19)4-7/h2-6,17-19,21H,1H3

Upstream product

• 857617-60-8 2-benzoyloxy-1-(2,4-dihydroxy-6-methoxy-phenyl)-ethanone 
• 854693-27-9 3,4-bis-benzoyloxy-benzoic acid-anhydride 
• 117-39-5 quercetol 
• 157650-21-0 5-O-Methyl-3,3',4',7-Tetrapivaloyl-Quercetin 
• 1592-68-3 2-(3,4-bis(benzyloxy)phenyl)-3,7-(dibenzyloxy)-5-methoxy-4H-chromen-4-one 
• 1486-63-1 3,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]-5-hydroxy-4H-1-benzopyran-4-one 
• 157650-20-9 2-(3,4-bis(pivaloyloxy)phenyl)-5-hydroxy-4-oxo-4H-chromene-3,7-diyl bis(2,2-dimethylpropanoate) 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 1393953-70-2 3,7-bis(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-methoxy-4H-chromen-4-one 
• 357194-03-7 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one 
• 1620516-62-2 3,7,3',4'-tetrahydroxy-5-methoxyflavone 7-O-β-D-glucopyranoside 
• 13157-90-9 2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)chromen-4-one 

Downstream Products

• 2174-64-3 5-methoxyresorcinol 

Relevant articles and documents

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Effects of Functional Groups and Sugar Composition of Quercetin Derivatives on Their Radical Scavenging Properties

Quercetin derivatives are widespread in the plant kingdom and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of quercetin derivatives, with a focus on the influence of functional groups and sugar composition on their antioxidant capacity. A series of quercetin derivatives were therefore prepared and assessed for their DPPH radical scavenging properties. Isoquercetin O-gallates were more potent radical scavengers than quercetin. The systematic analysis highlights the importance of the distribution of hydroxy substituents in isoquercetin O-gallates to their potency.

Biological evaluation and SAR analysis of O-methylated analogs of quercetin as inhibitors of cancer cell proliferation

Preclinical Research Using a high-throughout screening approach, the anticancer activities of 16 O-methylated (OMe) analogs of quercetin were assessed. The structure-activity relationships showed that OMe moieties at the 4′ and/or 7 positions were important for maintaining inhibitory activities against the 16 cancer cell lines. Furthermore, when the OH groups at the 3′ and 4′ positions were both replaced by OMe moieties, anticancer activity was enhanced.