110420-64-9

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-5,8-dimethoxy-
• CAS NO: 110420-64-9
• Molecular Formula: C17H14O6
• Molecular Weight: 314.295
• Mol File: 110420-64-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-5,8-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-5,8-dimethoxy-(110420-64-9)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-5,8-dimethoxy-(110420-64-9)

Safety Data

• Hazardous Substances Data: 110420-64-9(Hazardous Substances Data)

Upstream product

• 20032-42-2 2,5-dimethoxyresorcinol 
• 204591-02-6 2-(4-Benzyloxy-phenyl)-1-(2,4-bis-benzyloxy-3,6-dimethoxy-phenyl)-3,3-dimethoxy-propan-1-one 
• 54121-34-5 (Z)-3-(4-Benzyloxy-phenyl)-1-(2,4-bis-benzyloxy-3,6-dimethoxy-phenyl)-propenone 
• 3162-51-4 1-(2,4-Bis-benzyloxy-3,6-dimethoxy-phenyl)-ethanone 
• 204591-12-8 1-(2,4-Dihydroxy-3,6-dimethoxy-phenyl)-2-(4-hydroxy-phenyl)-3,3-dimethoxy-propan-1-one 
• 101169-69-1 2,4,4'-trihydroxy-3,6-dimethoxy-deoxybenzoin 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 114003-37-1 7-acetoxy-3-(4-acetoxy-phenyl)-5,8-dimethoxy-chromen-4-one 
• 204591-30-0 Acetic acid 3-(4-acetoxy-phenyl)-5-hydroxy-8-methoxy-4-oxo-4H-chromen-7-yl ester 
• 27181-88-0 5,7-diacetoxy-3-(4-acetoxy-phenyl)-8-methoxy-chromen-4-one 
• 13111-57-4 4',5,7-trihydroxy-8-methoxyisoflavone 

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.