14549-84-9

Basic information

• Product Name: 2-(3,4-DIMETHOXY-PHENYL)-5,7-DIHYDROXY-3-METHOXY-CHROMEN-4-ONE
• Synonyms: 2-(3,4-DIMETHOXY-PHENYL)-5,7-DIHYDROXY-3-METHOXY-CHROMEN-4-ONE
• CAS NO: 14549-84-9
• Molecular Formula: C₁₈H₁₆O₇
• Molecular Weight: 344.31544
• Mol File: 14549-84-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 571.1°Cat760mmHg
• Flash Point: 209.7°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 1.21E-13mmHg at 25°C
• Refractive Index: 1.653
• CAS DataBase Reference: 2-(3,4-DIMETHOXY-PHENYL)-5,7-DIHYDROXY-3-METHOXY-CHROMEN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-DIMETHOXY-PHENYL)-5,7-DIHYDROXY-3-METHOXY-CHROMEN-4-ONE(14549-84-9)
• EPA Substance Registry System: 2-(3,4-DIMETHOXY-PHENYL)-5,7-DIHYDROXY-3-METHOXY-CHROMEN-4-ONE(14549-84-9)

Safety Data

• Hazardous Substances Data: 14549-84-9(Hazardous Substances Data)

Usage

Natural occurrence

Found in various plants and herbs such as red clover and alfalfa.

Classification

Belongs to the class of compounds known as isoflavones.

Health benefits

Has potential health benefits including antioxidant, anti-inflammatory, and estrogenic properties.

Anti-cancer properties

Exhibits anti-cancer properties and may help in preventing the development and progression of certain types of cancers.

Treatment potential

Has potential in the treatment of menopausal symptoms and osteoporosis.

Research status

Being researched for its therapeutic uses.

InChI:InChI=1/C18H16O7/c1-22-12-5-4-9(6-13(12)23-2)17-18(24-3)16(21)15-11(20)7-10(19)8-14(15)25-17/h4-8,19-20H,1-3H3

Upstream product

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Downstream Products

• 62506-93-8 7-benzyloxy-2-(3,4-dimethoxy-phenyl)-5-hydroxy-3-methoxy-chromen-4-one 
• 62506-94-9 2-(3,4-dimethoxy-phenyl)-5,7,8-trihydroxy-3-methoxy-chromen-4-one 
• 1192136-02-9 5-(3-methylbut-2-enyloxy)-3-methoxy-7-(methoxymethoxy)-2-(3,4-dimethoxyphenyl)-4H-chromen-4-one 
• 1192135-66-2 5,7-dihydroxy-8-(3-hydroxy-3-methylbutyl)-3-methoxy-2-(3,4-dimethoxyphenyl)-4H-chromen-4-one 
• 1005737-95-0 5,7-dihydroxy-3-methoxy-2-(3,4-dimethoxyphenyl)-8-(3-methylbut-2-enyl)-4H-chromen-4-one 
• 1204813-10-4 5-hydroxy-3-methoxy-7-(methoxymethoxy)-2-(3,4-dimethoxyphenyl)-8-(3-methylbut-2-enyl)-4H-chromen-4-one 
• 1192136-01-8 5-hydroxy-3-methoxy-7-(methoxymethoxy)-2-(3,4-dimethoxyphenyl)-4H-chromen-4-one 
• 83206-86-4 2-(3,4-dimethoxy-phenyl)-5-hydroxy-3,7-dimethoxy-8-methyl-chromen-4-one 
• 102948-63-0 7-benzyloxy-2-(3,4-dimethoxy-phenyl)-3,5-dimethoxy-chromen-4-one 
• 54945-85-6 2-(3,4-dimethoxy-phenyl)-3,5,7-trimethoxy-8-methyl-chromen-4-one 
• 96308-83-7 2-(3,4-dimethoxy-phenyl)-5,7-dihydroxy-3-methoxy-8-methyl-chromen-4-one 
• 859050-38-7 2-(3,4-dimethoxy-phenyl)-5,8-dihydroxy-3-methoxy-chromen-4-one 
• 54987-82-5 3,5,7,3',4'-pentahydroxy-8-methylflavone 
• 70460-38-7 2-(3,4-dimethoxy-phenyl)-5-hydroxy-3-methoxy-chromen-4-one 

Relevant articles and documents

Quercetin analogs with high fetal hemoglobin-inducing activity

β-Thalassemia is the major health problems in developing countries, when affected patients and healthy carriers are numerous, resulting a total absence or severe decrease in the production of β-globin chains. The use of chemical agents for increasing the production of fetal hemoglobin (HbF) by reactivating γ-globin gene to balance excess α-globin chains is an alternative therapeutic approach. Therefore, the search for molecules exhibiting the property of inducing γ-globin gene expression is of great interest. In this report, we discovered that quercetin (1), the major flavonoid isolated from the heartwoods of the medicinal plant Anaxagorea luzonensis promoted the expression of γ-globin gene. Chemical modification of 1 to fourteen methyl ether analogs (2?15) was conducted. The structures of these compounds were established on the basis of their spectroscopic data and by comparison with those of the reported values. The parent flavonoid and its chemically modified analogs were investigated for their γ-globin gene induction for the first time. The parent compound 1 exhibited less induced γ-globin gene expression than cisplatin and hemin, the positive controls. 3,4′-Di-O-methylquercetin (7), the modified analog, significantly enhanced γ-globin gene expression with 2.6-fold change at 8 μM, which was slightly higher than cisplatin and hemin. Moreover, compounds 1 and 7 displayed less cytotoxic activity against K562::ΔGγAγEGFP cells than cisplatin. Structure-activity relationship (SAR) study revealed that the methoxyl groups at the 3- and 4?-positions and the free hydroxyl group at the 7-position are required for strong HbF-inducing activity.

Effects of flavonoids on cell proliferation and caspase activation in a human colonic cell line HT29: An SAR study

A library of 42 natural and synthetic flavonoids has been screened for their effect on cell proliferation and apoptosis in a human colonic cell line (HT-29). Examples of different classes of flavonoids have been screened, and the effects of hydroxylation, methoxylation and/or C-alkylation at various positions in the A- and B-rings have been assessed. Flavones and flavonols possess greater antiproliferative activity than chalcones and flavanones. With respect to structural modification of flavonoids, C-isoprenylation was by far the most effective, with substitution at the 8-position and longer chains, such as geranyl giving the best results. Finally, most compounds that significantly reduced cell survival also increased caspase activity, suggesting that at least part of their antiproliferative activity might be attributable to an apoptotic response.