104481-00-7

Basic information

• Product Name: 1-(6-hydroxy-2,4-dimethoxy-3-methoxymethoxyphenyl)-ethanone
• Synonyms: 1-(6-hydroxy-2,4-dimethoxy-3-methoxymethoxyphenyl)-ethanone
• CAS NO: 104481-00-7
• Molecular Weight: 256.255
• Mol File: 104481-00-7.mol

Chemical Properties

• CAS DataBase Reference: 1-(6-hydroxy-2,4-dimethoxy-3-methoxymethoxyphenyl)-ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(6-hydroxy-2,4-dimethoxy-3-methoxymethoxyphenyl)-ethanone(104481-00-7)
• EPA Substance Registry System: 1-(6-hydroxy-2,4-dimethoxy-3-methoxymethoxyphenyl)-ethanone(104481-00-7)

Safety Data

• Hazardous Substances Data: 104481-00-7(Hazardous Substances Data)

Upstream product

• 6962-57-8 3,6-dihydroxy-2,4-dimethoxyacetophenone 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 104481-01-8 6'-hydroxy-2',4'-dimethoxy-3'-methoxymethoxy-2-<3,4-bis(benzyloxy)benzoyl>acetophenone 
• 944828-45-9 1-(2,4-dimethoxy-3,6-dimethoxymethoxyphenyl)-ethanone 
• 104481-06-3 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[5-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-7-methoxy-4-oxo-4H-chromen-6-yloxy]-tetrahydro-pyran-3-yl ester 
• 104481-07-4 5-Benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-7-methoxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromen-4-one 
• 104481-04-1 6-acetoxy-3',4',5-tris(benzyloxy)-7-dimethoxyflavone 
• 104481-05-2 6-hydroxy-3',4',5-tris(benzyloxy)-7-dimethoxyflavone 
• 104495-50-3 6-acetoxy-3',4'-bis(benzyloxy)-5,7-dimethoxyflavone 
• 104481-02-9 6-acetoxy-3',4'-bis(benzyloxy)-5-hydroxy-7-dimethoxyflavone 
• 104481-03-0 3',4'-bis(benzyloxy)-5,6-dihydroxy-7-dimethoxyflavone 
• 170234-91-0 2-(3,4-Bis-benzyloxy-phenyl)-5,7-dimethoxy-6-methoxymethoxy-chromen-4-one 
• 170234-94-3 Toluene-4-sulfonic acid 5,7-dimethoxy-6-methoxymethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl ester 
• 170234-99-8 Acetic acid 2-(3-acetoxy-4-methoxy-phenyl)-5,7-dimethoxy-6-methoxymethoxy-4-oxo-4H-chromen-3-yl ester 
• 170234-95-4 Acetic acid 2-(4-acetoxy-3-methoxy-phenyl)-5,7-dimethoxy-6-methoxymethoxy-4-oxo-4H-chromen-3-yl ester 
• 170234-74-9 2-(4-Benzyloxy-3-methoxy-phenyl)-3-hydroxy-5,7-dimethoxy-6-methoxymethoxy-chromen-4-one 

Relevant articles and documents

Studies of the selective O-alkylation and dealkylation of flavonoids. XVIII. A convenient method for synthesizing 3,5,6,7-tetrahydroxyflavones

In the demethylation of 6-hydroxy-3,4',7-trimethoxy-5-(tosyloxy)flavone with anhydrous aluminum bromide, the 5-tosyloxyl group was eliminated with bromination to give 8-bromo-3,6,7-trihydroxy-4'-methoxyflavone as the main product. When anhydrous aluminum chloride was used in the demethylation of the acetate, the 5-tosyloxyl group was cleaved prior to the demethylation to give 5,6,7-trihydroxy-3,4'-dimethoxyflavone. Demethylation of 6-hydroxy-4',5,7-trimethoxy-3-(tosyloxy)flavone and its acetate with the bromide or chloride afforded the 5,6,7-trihydroxyflavone without the cleavage of the 3-tosyloxyl group, but was not suitable for the general synthesis of the 3,5,6,7-tetrahydroxyflavones because of the difficulty in removing the protecting group. Consequently, it was found that the direct demethylation of 3,6-dihydroxy-5,7-dimethoxyflavones with anhydrous aluminum chloride-sodium iodide in acetonitrile was the most useful general method for synthesizing 3,5,6,7-tetrahydroxyflavones. Additionally, the reported structures of two natural flavones were revised.

Preparation of two sets of 5,6,7-trioxygenated dihydroflavonol derivatives as free radical scavengers and neuronal cell protectors to oxidative damage

An unusual class of 5,6,7-trioxygenated dihydroflavonols (3a-e and 4a-j) were designed and prepared. Their antioxidative properties were assessed by examining their capacities in several in vitro models, including superoxide anion and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, rat liver homogenate lipid peroxidation inhibition, PC12 cells protection from oxidative damage, and xanthine oxidase inhibition. These dihydroflavonols displayed positive quenching abilities towards O2{radical dot} - and DPPH free radicals, in which the majority exhibited superior antioxidant properties to Vitamin C. cis-Configurated compound (±)-3e demonstrated remarkable inhibition to LPO with an IC50 value of 1.9 ± 0.3 μM, which was apparently stronger than that of quercetin (IC50 = 6.0 ± 0.4 μM). trans-Configurated dihydroflavonol (±)-4h exhibited significant protective effect on PC12 cells against oxidative damage with an EC50 value of 41.5 ± 5.3 μM, more effective compared to that of quercetin (EC50 = 81.8 ± 8.7 μM). The 6-OH-5,7-dimethoxy analogue (±)-3d showed significant inhibition of xanthine oxidase with an IC50 value of 16.0 ± 0.8 μM, which is superior to that of allopurinol (IC50 = 23.5 ± 2.0 μM). In addition to the hypothesized action mechanism of the bio-active compounds, 3D modeling was used to analyze the relationship between the minimized-energy structures and antioxidant activities.