529-40-8

Basic information

• Product Name: 4',7-DIMETHOXY-3,3',5-TRIHYDROXYFLAVONE
• Synonyms: OMBUIN;QUERCETIN-7,4'-DIMETHYL ETHER;3,5-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-4h-1-benzopyran-4-on;4’,7-dimethoxy-3,3’,5-trihydroxy-flavon;7,4’-di-o-methylquercetin;4',7-DIMETHOXY-3,3',5-TRIHYDROXYFLAVONE;2-(3-Hydroxy-4-methoxyphenyl)-7-methoxy-3,5-dihydroxy-4H-1-benzopyran-4-one;3,3',5-Trihydroxy-4',7-dimethoxyflavone
• CAS NO: 529-40-8
• Molecular Formula: C₁₇H₁₄O₇
• Molecular Weight: 330.29
• EINECS: 200-258-5
• Product Categories: Flavanols
• Mol File: 529-40-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 229-230 °C
• Boiling Point: 593.7°Cat760mmHg
• Flash Point: 222.1°C
• Appearance: /
• Density: 1.507g/cm³
• Vapor Pressure: 6.08E-15mmHg at 25°C
• Refractive Index: 1.681
• Storage Temp.: 2-8°C
• PKA: 6.15±0.40(Predicted)
• CAS DataBase Reference: 4',7-DIMETHOXY-3,3',5-TRIHYDROXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4',7-DIMETHOXY-3,3',5-TRIHYDROXYFLAVONE(529-40-8)
• EPA Substance Registry System: 4',7-DIMETHOXY-3,3',5-TRIHYDROXYFLAVONE(529-40-8)

Safety Data

• Hazardous Substances Data: 529-40-8(Hazardous Substances Data)

Usage

Uses

Ombuin is a synthetic flavonoid which displays activity as a potent mycobacterium tuberculosis inhibitor.

InChI:InChI=1/C17H14O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-12(23-2)10(18)5-8/h3-7,18-19,21H,1-2H3

Upstream product

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• 28590-40-1 3',5-dihydroxy-4',7-dimethoxydihydroflavone 
• 520-33-2 hesperetin 
• 498548-19-9 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-7-methoxy-4H-chromen-4-one 
• 498548-17-7 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-4H-chromen-4-one 
• 357194-03-7 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one 
• 77-78-1 dimethyl sulfate 
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Downstream Products

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Relevant articles and documents

Flavonoid compound as well as synthesis method and application thereof

The invention relates to a semi-synthetic flavonoid compound and an anti-inflammatory application thereof. The invention belongs to the technical field of medicines, particularly relates to synthesis of derivatives of natural products and an application of the derivatives in the anti-inflammatory aspect, and more particularly relates to a synthesis method of flavonoid compounds and an application of the flavonoid compounds in the anti-inflammatory aspect. According to the method, hesperetin is taken as a raw material, flavonol aglycone is synthesized, and finally flavonoid glycoside is synthesized through debenzylation and acetyl reaction. According to the invention, 32 flavonoid compounds, including 14 flavonoid aglycones and 18 flavonoid glycosides, including 15 known compounds and 17 unreported compounds, are synthesized in total. The part of the compounds show good in-vitro anti-inflammatory activity and can become anti-inflammatory drugs or lead compounds.

Synthesis of Rhamnazin and Ombuin as methylated metabolites of quercetin

The methylated metabolites of quercetin, rhamnazin and ombuin are highly likely to develop as anticancer and anti-inflammatory agents. In this study, we synthesized rhamnazin through selective methylation of quercetin hydroxyl group, which has not been reported so far. In addition, a new synthetic method was developed to correct the problems of previous synthetic method of ombuin, one of the methylated metabolites of quercetin.

Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK

In order to understand the effect of structure-activity relationships on melanogenesis using B16 melanoma cells, 19 quercetin derivatives were synthesized. Among the synthesized compounds, 3-O-methylquercetin (11) and 3′,4′,7-O-trimethylquercetin (14) increased melanin content more potently than the positive control theophylline, while exhibiting low cytotoxicity. Compound 11 exhibited less melanogenesis-stimulating activity than compound 14. However, 11 increased the expression of tyrosinase and tyrosinase-related protein 1 (TRP-1) to a greater extent than 14, thereby suggesting that melanogenesis in melanoma cells does not depend solely on the expression of the enzymes catalyzing melanin biosynthesis. Furthermore, 14 also stimulated the expression of the microphthalmia-associated transcription factor (MITF) and p-p38 mitogen activated protein kinase (MAPK), while they were not increased by 11. These results suggest that 11 may enhance the expression of tyrosinase and TRP-1 by regulating the proteasomal degradation of melanogenic enzymes and/or by activating other transcriptional factors regulating enzyme expression.