4332-74-5

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-6-methoxy-3-(4-methoxyphenyl)-
• CAS NO: 4332-74-5
• Molecular Formula: C21H18O8
• Molecular Weight: 398.369
• Mol File: 4332-74-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-6-methoxy-3-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-6-methoxy-3-(4-methoxyphenyl)-(4332-74-5)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-6-methoxy-3-(4-methoxyphenyl)-(4332-74-5)

Safety Data

• Hazardous Substances Data: 4332-74-5(Hazardous Substances Data)

Upstream product

• 204590-55-6 1-(4,6-Bis-benzyloxy-2,3-dimethoxy-phenyl)-3,3-dimethoxy-2-(4-methoxy-phenyl)-propan-1-one 
• 204591-53-7 Acetic acid 5,6-dimethoxy-3-(4-methoxy-phenyl)-4-oxo-4H-chromen-7-yl ester 
• 53505-61-6 7-hydroxy-4',5,6-trimethoxyisoflavone 
• 2345-17-7 4'-methoxytectorigenin 
• 108-24-7 acetic anhydride 

Downstream Products

• 96300-23-1 5,7-diacetoxy-6-methoxy-3-(4'-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one 

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.

ISOFLAVONOIDS FROM THE HEARTWOOD OF PTEROCARPUS MARSUPIUM

Three new isoflavone glysocisides viz retusin 7-glucoside, irisolidone 7-rhamnodise and 5,7-dihydroxy-6-methoxyisoflavone 7-rhamnodiside have been isolated from the heartwood of Pterocarpus marsupium. - Key Word Index: Pterocarpus marsupium; Leguminosae; retusin 7-glucoside; irisolidone 7-rhamnoside and 5,7-dihydroxy-6-methoxyisoflavone 7-rhamnoside.