204590-59-0

Basic information

• Product Name: (Z)-3-(4-Benzyloxy-phenyl)-1-(4,6-bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-propenone
• Synonyms: (Z)-3-(4-Benzyloxy-phenyl)-1-(4,6-bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-propenone
• CAS NO: 204590-59-0
• Molecular Weight: 614.738
• Mol File: 204590-59-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-3-(4-Benzyloxy-phenyl)-1-(4,6-bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-propenone(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-3-(4-Benzyloxy-phenyl)-1-(4,6-bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-propenone(204590-59-0)
• EPA Substance Registry System: (Z)-3-(4-Benzyloxy-phenyl)-1-(4,6-bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-propenone(204590-59-0)

Safety Data

• Hazardous Substances Data: 204590-59-0(Hazardous Substances Data)

Upstream product

• 4397-53-9 p-benzyloxybenzaldehyde 
• 204590-57-8 1-(4,6-Bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-ethanone 
• 100-44-7 benzyl chloride 
• 188927-31-3 4-benzyloxy-6-hydroxy-3-methoxy-2-isopropoxyacetophenone 

Downstream Products

• 204590-61-4 2-(4-Benzyloxy-phenyl)-1-(4,6-bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-3,3-dimethoxy-propan-1-one 
• 204590-62-5 7-Hydroxy-3-(4-hydroxy-phenyl)-5-isopropoxy-6-methoxy-chromen-4-one 
• 41106-68-7 5,7-diacetoxy-3-(4-acetoxy-phenyl)-6-methoxy-chromen-4-one 
• 548-77-6 tectorigenin 

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.