520-12-7

Basic information

• Product Name: 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone
• Synonyms: 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone;5,7-dihydroxy-4',6-dimethoxyflavone;PECTOLINARIGENIN;5,7-Dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one;6-Methoxyacacetin;6-O,4'-O-Dimethylapigenin;Pectolinaringenin;Scutellarein 4',6-dimethyl ether
• CAS NO: 520-12-7
• Molecular Formula: C₁₇H₁₄O₆
• Molecular Weight: 314.28946
• EINECS: 208-286-0
• Product Categories: Tri-substituted Flavones;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 520-12-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 220-223°
• Boiling Point: 565.5°Cat760mmHg
• Flash Point: 212.3°C
• Appearance: /
• Density: 1.402g/cm³
• Vapor Pressure: 2.15E-13mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 6.49±0.40(Predicted)
• CAS DataBase Reference: 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone(520-12-7)
• EPA Substance Registry System: 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone(520-12-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 520-12-7(Hazardous Substances Data)

Usage

Description

5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone is a dimethoxyflavone derivative, which is a type of flavonoid compound. It is characterized by the presence of two hydroxyl groups at the 5 and 7 positions, a methoxy group at the 6 position, and a 4-methoxyphenyl group at the 2 position. 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone is known for its pharmacological properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone is used as a pharmaceutical agent for its potential therapeutic effects. 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone's structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs.
Used in Anticancer Applications:
In the field of oncology, 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone is used as an anticancer agent. It may exhibit inhibitory effects on tumor growth and progression by modulating various oncological signaling pathways. Additionally, it could potentially enhance the efficacy of conventional chemotherapeutic drugs when used in combination.
Used in Drug Delivery Systems:
To improve the bioavailability and therapeutic outcomes of 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone, novel drug delivery systems have been developed. These systems, which may include organic and metallic nanoparticles, serve as carriers for the compound, enhancing its delivery to target cells and tissues.
Used in Antimicrobial Applications:
5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone is used as an antimicrobial agent, particularly against uropathogens. Its pharmacological activity makes it a potential candidate for the development of new treatments for urinary tract infections.
Used in Nutraceutical Industry:
Due to its potential health benefits, 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyrone may also be used in the nutraceutical industry. It could be incorporated into dietary supplements or functional foods to provide consumers with additional health-promoting properties.

InChI:InChI=1/C17H14O6/c1-21-10-5-3-9(4-6-10)13-7-11(18)15-14(23-13)8-12(19)17(22-2)16(15)20/h3-8,19-20H,1-2H3

Upstream product

• 25893-02-1 7-benzyloxy-5,6-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 7499-99-2 1-(2,4-dihydroxy-3,6-dimethoxy)phenylethanone 
• 794-94-5 p-Methoxybenzoic anhydride 
• 529-53-3 scutellarein 
• 53452-12-3 6,4'-dimethoxy-5-hydroxyflavone 7-O-β-D-glucopyranoside 
• 20032-42-2 2,5-dimethoxyresorcinol 
• 25892-94-8 1-(4-(benzyloxy)-3,6-dihydroxy-2-methoxyphenyl)ethan-1-one 
• 77733-15-4 7-hydroxy-5,6,4'-trimethoxyflavone 
• 28978-02-1 pectolinarin 
• 27740-01-8 scutellarin 
• 1105056-24-3 9-hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one 
• 1447-88-7 hispidulin 
• 74-88-4 methyl iodide 
• 1402607-40-2 9-hydroxy-2,2-diphenyl-6-[4-(phenylmethoxy)phenyl]-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one 

Downstream Products

• 203191-22-4 7-carboxymethyloxy-5-hydroxy-4',6-dimethoxy flavone 
• 1087318-94-2 C₂₁H₂₃NO₆ 
• 1087318-96-4 C₂₃H₂₇NO₆ 
• 1087318-92-0 C₂₂H₂₅NO₆ 
• 1087319-00-3 C₂₄H₂₇NO₆ 
• 1087318-98-6 C₂₃H₂₅NO₆ 
• 1087319-02-5 C₂₃H₂₅NO₇ 

Relevant articles and documents

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Pubescidin, an isoflavone glycoside from Centrosema pubescens

A new isoflavone glycoside, irisolidone 7-O-β-D-apiofuranosyl-(1 → 2)- β-D-glucopyranoside was isolated from the seeds of Centrosema pubescens along with sitosterol, stigmasterol and sitosterol 3-O-β-D-glucopyranoside. The structures of new and known compounds were established by spectroscopic and chemical methods.

Semi-synthesis of a series natural flavonoids and flavonoid glycosides from scutellarin

Natural flavonoids and flavonoid glycosides exist in many plants and have been demonstrated to possess various clinically relevant properties, isolating large amounts of these compounds that have striking structural similarity from plant sources needs tedious isolation techniques. These processes limited their availability in structural diversity for structure?activity relationship (SAR) studies, and restrict large quantities for, as an example, their mechanistic evaluation of the in vivo activities. In this work, we developed a semi-synthetic strategy from scutellarin for the synthesis of a series of natural flavonoids and flavonoid glycosides. By taking this strategy, eight bioactive flavonoids with striking structural similarities were synthesized efficiently and practically. The sufficient amounts obtained products will greatly facilitate the SAR studies and mechanistic evaluation of the in vivo activities.

In vitro biological evaluation of novel 7-O-dialkylaminoalkyl cytotoxic pectolinarigenin derivatives against a panel of human cancer cell lines

The effect of novel pectolinarigenin derivatives bearing a dialkylaminoalkyl substituent at O-7 on cell proliferation was evaluated in vitro in a panel of seven human cancer cell lines including renal adenocarcinoma ACHN, amelanotic melanoma C32, colorectal adenocarcinoma Caco-2, lung large cell carcinoma COR-L23, malignant melanoma A375, lung carcinoma A549 and hepatocellular carcinoma Huh-7D12 cell lines. Pectolinarigenin (2), obtained by hydrolysis of rutinose unit of the pectolinarin (1) isolated from Linaria reflexa, exhibited cytotoxic activity against Caco-2, A549 and A375 cell lines with IC50 values of 5.3-8.2 μM. The most active pectolinarigenin derivative was 3 characterized by a dimethylamino-propoxy group in O-7 with IC50 values of 7.2 and 7.4 μM against COR-L23 and A549 cell lines, respectively. A structure-activity relationship analysis of synthesized compounds was performed. None of the tested compounds affected the proliferation of skin fibroblasts 142BR suggesting a selective activity against tumor cells.