39012-01-6

Basic information

• Product Name: 3',6-Dimethoxy-4',5,7-trihydroxyisoflavone
• Synonyms: 3',6-Dimethoxy-4',5,7-trihydroxyisoflavone;3-[4-Hydroxy-3-methoxyphenyl]-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one;5,7,4'-Trihydroxy-6,3'-dimethoxyisoflavone;Iristectorigenin B
• CAS NO: 39012-01-6
• Molecular Formula: C₁₇H₁₄O₇
• Molecular Weight: 330.2889
• Mol File: 39012-01-6.mol

Chemical Properties

• Boiling Point: 619°Cat760mmHg
• Flash Point: 232°C
• Appearance: /
• Density: 1.483g/cm³
• Vapor Pressure: 6.48E-16mmHg at 25°C
• Refractive Index: 1.67
• CAS DataBase Reference: 3',6-Dimethoxy-4',5,7-trihydroxyisoflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 3',6-Dimethoxy-4',5,7-trihydroxyisoflavone(39012-01-6)
• EPA Substance Registry System: 3',6-Dimethoxy-4',5,7-trihydroxyisoflavone(39012-01-6)

Safety Data

• Hazardous Substances Data: 39012-01-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3',6-Dimethoxy-4',5,7-trihydroxyisoflavone is used as a therapeutic agent for its antioxidant, anti-inflammatory, and anti-cancer properties. Its antioxidant activity helps protect cells from free radical damage, while its anti-inflammatory effects may reduce the risk of chronic diseases. Additionally, the compound has shown potential in inhibiting the growth and spread of cancer cells, making it an interesting area of research for cancer treatment and prevention.
Used in Dietary Supplements:
3',6-Dimethoxy-4',5,7-trihydroxyisoflavone is used as an ingredient in dietary supplements to provide health benefits associated with its antioxidant, anti-inflammatory, and anti-cancer properties. It may help support overall health and well-being by reducing oxidative stress, inflammation, and the risk of certain cancers.

InChI:InChI=1/C17H14O7/c1-22-12-5-8(3-4-10(12)18)9-7-24-13-6-11(19)17(23-2)16(21)14(13)15(9)20/h3-7,18-19,21H,1-2H3

Upstream product

• 204591-46-8 2-(4-Benzyloxy-3-methoxy-phenyl)-1-(4,6-bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-3,3-dimethoxy-propan-1-one 
• 204591-44-6 (Z)-3-(4-Benzyloxy-3-methoxy-phenyl)-1-(4,6-bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-propenone 
• 204590-57-8 1-(4,6-Bis-benzyloxy-2-isopropoxy-3-methoxy-phenyl)-ethanone 
• 188927-31-3 4-benzyloxy-6-hydroxy-3-methoxy-2-isopropoxyacetophenone 
• 204591-48-0 7-Hydroxy-3-(4-hydroxy-3-methoxy-phenyl)-5-isopropoxy-6-methoxy-chromen-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.