57826-76-3

Upstream product

• 56419-18-2 5,7-dihydroxy-3-(3-hydroxy-4-methoxy-phenyl)-8-methoxy-chromen-4-one 
• 108-24-7 acetic anhydride 
• 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 
• 204591-33-3 Acetic acid 3-(3-acetoxy-4-methoxy-phenyl)-5-hydroxy-8-methoxy-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 
• 64640-61-5 7-hydroxy-3-(3-hydroxy-4-methoxy-phenyl)-5,8-dimethoxy-chromen-4-one 

Relevant academic research and scientific papers

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.