16290-50-9

Basic information

• Product Name: 5,7-dimethoxy-4'-hydroxyflavone
• Synonyms: 5,7-dimethoxy-4'-hydroxyflavone
• CAS NO: 16290-50-9
• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.29
• Mol File: 16290-50-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 532.4°Cat760mmHg
• Flash Point: 200.3°C
• Appearance: /
• Density: 1.321g/cm³
• CAS DataBase Reference: 5,7-dimethoxy-4'-hydroxyflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-dimethoxy-4'-hydroxyflavone(16290-50-9)
• EPA Substance Registry System: 5,7-dimethoxy-4'-hydroxyflavone(16290-50-9)

Safety Data

• Hazardous Substances Data: 16290-50-9(Hazardous Substances Data)

Upstream product

• 921942-45-2 2-(4-aminophenyl)-5,7-dimethoxy-4H-chromen-4-one 
• 22812-15-3 2-[4-(benzyloxy)phenyl]-5,7-dimethoxy-4H-chromen-4-one 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 19158-99-7 (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 836608-01-6 2-(4-nitrophenyl)-5,7-dimethoxy-4H-chromen-4-one 
• 125553-69-7 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-nitrophenyl)propane-1,3-dione 
• 76554-28-4 C₂₀H₂₀O₅ 
• 1167577-15-2 C₂₀H₁₈O₅ 
• 40663-68-1 4-(2-propenyloxy)benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 108-73-6 3,5-dihydroxyphenol 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 21392-57-4 Dimethyl-chrysin 
• 5631-70-9 4',5,7-trimethoxyflavone 

Downstream Products

• 22812-39-1 2-(4-acetoxy-phenyl)-5,7-dimethoxy-chromen-4-one 
• 437-64-9 genkwanin 
• 87617-79-6 C₃₅H₂₈O₁₀ 
• 1612891-70-9 2-(4-(2-bromoethoxy)phenyl)-5,7-dimethoxychromen-4-one 
• 1612891-84-5 5,7-dimethoxy-2-(4-oxiranylmethoxyphenyl)chromen-4-one 
• 1612891-76-5 5,7-dimethoxy-2-(4-(2-piperidin-1-ylethoxy)phenyl)chromen-4-one 
• 1612891-77-6 5,7-dimethoxy-2-(4-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)chromen-4-one 
• 1612891-78-7 5,7-dimethoxy-2-(4-(2-pyrrolidin-1-ylethoxy)phenyl)chromen-4-one 
• 1612891-79-8 2-(4-(2-diethylaminoethoxy)phenyl)-5,7-dimethoxychromen-4-one 
• 1612891-81-2 5,7-dimethoxy-2-(4-(piperidin-4-yloxy)phenyl)chromen-4-one 
• 1612891-82-3 2-(4-(2-aminoethoxy)phenyl)-5,7-dimethoxychromen-4-one 
• 1612891-83-4 2-(4-(3-aminopropoxy)phenyl)-5,7-dimethoxychromen-4-one 
• 1612891-85-6 2-(4-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl)-5,7-dimethoxychromen-4-one 
• 1612891-86-7 2-(4-(2-hydroxy-3-pyrrolidin-1-ylpropoxy)phenyl)-5,7-dimethoxychromen-4-one 

Relevant articles and documents

Biotransformation of 5,7-Methoxyflavones by Selected Entomopathogenic Filamentous Fungi

5,7-Dimethoxyflavone, a chrysin derivative, occurs in many plants and shows very low toxicity, even at high doses. On the basis of this phenomenon, we biotransformed a series of methoxy-derivatives of chrysin, apigenin, and tricetin obtained by chemical synthesis. We used entomopathogenic fungal strains with the confirmed ability of simultaneous hydroxylation/demethylation and glycosylation of flavonoid compounds. Both the amount and the place of attachment of the methoxy group influenced the biotransformation rate and the product's amount nascent. Based on product and semi-product structures, it can be concluded that they are the result of cascading transformations. Only in the case of 5,7,3′,4′,5′-pentamethoxyflavone, the strains were able to attach a sugar molecule in place of the methoxy substituent to give 3′-O-β-d-(4″-O-methylglucopyranosyl)-5,7,4′,5′-tetramethoxyflavone. However, we observed the tested strains' ability to selectively demethylate/hydroxylate the carbon C-3′ and C-4′ of ring B of the substrates used. The structures of four hydroxyl-derivatives were determined: 4′-hydroxy-5,7-dimethoxyflavone, 3′-hydroxy-5,7-dimethoxyflavone, 3′-hydroxy-5,7,4′,5′-tetramethoxyflavone, and 5,7-dimethoxy-3′,4′-dihydroxyflavone (5,7-dimethoxy-luteolin).

Design, synthesis, and characterization of novel apigenin analogues that suppress pancreatic stellate cell proliferation in vitro and associated pancreatic fibrosis in vivo

Accumulating evidence suggests that activated pancreatic stellate cells (PSC) play an important role in chronic pancreatitis (CP), and inhibition of the activated PSC is considered as a potential strategy for the treatment and prevention of CP. Herein, we disclose our findings that apigenin and its novel analogues suppress the proliferation and induce apoptosis in PSC, which reduce the PSC-mediated fibrosis in CP. Chemical modifications of apigenin have been directed to build a focused library of O-alkylamino-tethered apigenin derivatives at 4′-O position of the ring C with the attempt to enhance the potency and drug-like properties including aqueous solubility. A number of compounds such as 14, 16, and 24 exhibited potent antiproliferative effects as well as improved aqueous solubility. Intriguingly, apigenin, new analogues 23 and 24 displayed significant efficacy to reduce pancreatic fibrosis even at a low dose of 0.5 mg/kg in our proof-of-concept study using a preclinical in vivo mouse model of CP.

Flavone glycosides from the flowers of Morinda citrofolia

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