111796-47-5

Basic information

• Product Name: 6-methyl-3,5,7,3',4'-penta-O-methylquercetin
• Synonyms: 6-methyl-3,5,7,3',4'-penta-O-methylquercetin
• CAS NO: 111796-47-5
• Molecular Weight: 386.401
• Mol File: 111796-47-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-methyl-3,5,7,3',4'-penta-O-methylquercetin(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methyl-3,5,7,3',4'-penta-O-methylquercetin(111796-47-5)
• EPA Substance Registry System: 6-methyl-3,5,7,3',4'-penta-O-methylquercetin(111796-47-5)

Safety Data

• Hazardous Substances Data: 111796-47-5(Hazardous Substances Data)

Upstream product

• 96308-82-6 2-(3,4-dimethoxy-phenyl)-5,7-dihydroxy-3-methoxy-6-methyl-chromen-4-one 
• 77-78-1 dimethyl sulfate 
• 54945-91-4 2-(3,4-dimethoxy-phenyl)-5-hydroxy-3,7-dimethoxy-6-methyl-chromen-4-one 
• 117-39-5 quercetol 
• 74-88-4 methyl iodide 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 155334-77-3 2-(3,4-dimethoxy-phenyl)-5-hydroxy-3-methoxy-6-methyl-7-veratroyloxy-chromen-4-one 
• 104397-81-1 1-(4,6-dihydroxy-2-methoxy-3-methyl-phenyl)-2-methoxy-ethanone 
• 110333-13-6 2-methoxy-1-(2,4,6-trihydroxy-3-methyl-phenyl)-ethanone 
• 88-03-9 2,4,6-trihydroxytoluene 
• 16297-02-2 2,4,6-Trihydroxy-3,ω-dimethoxy-acetophenon 
• 7578-49-6 1-(6-hydroxy-2,4-dimethoxy-3-methyl-phenyl)-2-methoxy-ethanone 
• 24824-54-2 3,4-dimethoxybenzoic anhydride 

Downstream Products

• 54987-82-5 3,5,7,3',4'-pentahydroxy-8-methylflavone 
• 491-49-6 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methylchromen-4-one 

Relevant articles and documents

A simple and effective preparation of quercetin pentamethyl ether from quercetin

Among the five hydroxy (OH) groups of quercetin (3,5,7,3',4'-pentahydroxyflavone), the OH group at 5 position is the most resistant to methylation due to its strong intramolecular hydrogen bonding with the carbonyl group at 4 position. Thus, it is generally difficult to synthesize the pentamethyl ether efficiently by conventional methylation. Here, we describe a simple and effective perO-methylation of quercetin with dimethyl sulfate in potassium (or sodium) hydroxide/dimethyl sulfoxide at room temperature for about 2 hours, affording quercetin pentamethyl ether (QPE) quantitatively as a single product. When methyl iodide was used in place of dimethyl sulfate, the C-methylation product 6-methylquercetin pentamethyl ether was also formed. A computational study provided a rationale for the experimental results.