56419-18-2

Basic information

• Product Name: 5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4H-chromen-4-one
• CAS NO: 56419-18-2
• Molecular Formula: C₁₇H₁₄O₇
• Molecular Weight: 330.2889
• Mol File: 56419-18-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 599.5°C at 760 mmHg
• Flash Point: 224.3°C
• Density: 1.483g/cm³
• Vapor Pressure: 5.73E-15mmHg at 25°C
• Refractive Index: 1.67
• CAS DataBase Reference: 5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4H-chromen-4-one(56419-18-2)
• EPA Substance Registry System: 5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4H-chromen-4-one(56419-18-2)

Safety Data

• Hazardous Substances Data: 56419-18-2(Hazardous Substances Data)

Upstream product

• 64640-61-5 7-hydroxy-3-(3-hydroxy-4-methoxy-phenyl)-5,8-dimethoxy-chromen-4-one 
• 6274-74-4 2,6-dibenzyloxy-1,4-dimethoxybenzene 
• 38836-54-3 3-benzyloxy-4-methoxyphenylpyruvic acid oxime 
• 1699-39-4 2-(3-(benzyloxy)-4-methoxyphenyl)acetonitrile 
• 64640-60-4 2,4-dihydroxy-3,6-dimethoxyphenyl-3-hydroxy-4-methoxybenzyl ketone 
• 204591-06-0 2-(3-Benzyloxy-4-methoxy-phenyl)-1-(2,4-bis-benzyloxy-3,6-dimethoxy-phenyl)-3,3-dimethoxy-propan-1-one 
• 204590-96-5 (Z)-3-(3-Benzyloxy-4-methoxy-phenyl)-1-(2,4-bis-benzyloxy-3,6-dimethoxy-phenyl)-propenone 
• 204591-51-5 Acetic acid 3-(3-acetoxy-4-methoxy-phenyl)-5,8-dimethoxy-4-oxo-4H-chromen-7-yl ester 
• 204591-16-2 1-(2,4-Dihydroxy-3,6-dimethoxy-phenyl)-2-(3-hydroxy-4-methoxy-phenyl)-3,3-dimethoxy-propan-1-one 
• 3162-51-4 1-(2,4-Bis-benzyloxy-3,6-dimethoxy-phenyl)-ethanone 
• 204591-33-3 Acetic acid 3-(3-acetoxy-4-methoxy-phenyl)-5-hydroxy-8-methoxy-4-oxo-4H-chromen-7-yl ester 

Downstream Products

• 57826-76-3 3',5,7-Triacetyl-4',8-dimethoxy-isoflavon 

Relevant articles and documents

Studies of the selective O-Alkylation and dealkylation of flavonoids. XXIV. A convenient method for synthesizing 6- and 8-methoxylated 5,7- dihydroxyisoflavones

2',4'-Bis(benzyloxy)-3',6'-dimethoxychalcones (5), which were obtained from the dibenzyl ether of 2,4-dihydroxy-3,6-dimethoxyacetophenone (3), were oxidatively rearranged with thallium (III) nitrate in methanol and the resultant products were converted into 7-hydroxy-5,8-dimethoxyisoflavones (8) by hydrogenolysis, followed by cyclization. The isoflavones were quantitatively demethylated to 5,7-dihydroxy-8-methoxyisoflavones (2) via their acetates. The isomeric 5,7-dihydroxy-6-methoxyisoflavones (1) were also synthesized from the chalcones, obtained from 2,3-dimethoxy- (16) or 2- isopropoxy-3-methoxy-4,6-bis(benzyloxy)acetophenones (21), by a similar method. On the other hand, the isoflavones with two hydroxy groups at the 2'- and 4'-positions were easily synthesized by the following method. Treatment of the rearranged product from 2,2',4,4'-tetrakis(benzyloxy)-3'6'- dimethoxychalcone (5f) with hydrochloric acid (HCl) in acetic acid afforded 2',4',7-tris(benzyloxy)-5,8-dimethoxyisoflavone (10f). The 5-methoxy group in the isoflavone was quantitatively cleaved to give the corresponding 5- hydroxyisoflavone (11f), which was isomerized to 2',4',7-tris(benzyloxy)-5- hydroxy-6-methoxyisoflavone (25f) in the presence of anhydrous potassium carbonate. Hydrogenolysis of the two 5-hydroxyisoflavones proceeded smoothly to give 2',4',5,7-tetrahydroxy-8-(2f) and 6-methoxyisoflavones (1f), respectively. The 13C-NMR spectra of these isoflavones supported the proposed structures of polyhydroxyisoflavones. The proposed structures of two natural isoflavones were revised.