71479-92-0

Basic information

• Product Name: Araneol
• CAS NO: 71479-92-0
• Molecular Weight: 344.321
• Mol File: 71479-92-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Araneol(CAS DataBase Reference)
• NIST Chemistry Reference: Araneol(71479-92-0)
• EPA Substance Registry System: Araneol(71479-92-0)

Safety Data

• Hazardous Substances Data: 71479-92-0(Hazardous Substances Data)

Upstream product

• 151-10-0 1,3-Dimethoxybenzene 
• 1756-88-3 1,3,5-triamino-2,4-dimethoxybenzene 
• 1201-06-5 1,3,5-trihydroxy-2,4-dimethoxybenzene 
• 1630-09-7 2,4-dichloro-1,3,5-trinitrobenzene 
• 1150-40-9 1,3-dimethoxy-2,4,6-trinitrobenzene 
• 176662-12-7 7-Benzyloxy-3-hydroxy-5,6,8-trimethoxy-2-phenyl-chromen-4-one 
• 176662-06-9 1-(2,4-diacetoxy-3,5,6-trimethoxyphenyl)ethanone 
• 176662-07-0 1-(2-Hydroxy-3,5,6-trimethoxy-4-methoxymethoxy-phenyl)-ethanone 
• 56002-84-7 2,3,5,6-tetramethoxyphenyl acetate 
• 56002-81-4 1,2-dihydroxy-3,4,6-trimethoxybenzene 
• 7507-98-4 1-(2-hydroxy-3,4,6-trimethoxyphenyl)ethanone 
• 56002-82-5 2,3-diacetoxy-1,4,5-trimethoxy-benzene 
• 3152-06-5 7-benzyloxy-5,6,8-trimethoxy-2-phenyl-chromen-4-one 
• 3353-65-9 7-hydroxy-5,6,8-trimethoxy-2-phenyl-chromen-4-one 

Downstream Products

• 14221-85-3 3,5,6,7,8-pentamethoxyflavone 

Relevant articles and documents

Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. XXI.: A Convenient Method for Synthesizing 3,5,7-Trihydroxy-6,8-dimethoxyflavones and 5,7-Dihydroxy-3,6,8-trimethoxyflavones

The Friedel-Crafts acetylation with boron trifluoride was studied and it was found that 1-(2,4-dihydroxy-3,5,6-trimethoxyphenyl)ethanone was conveniently synthesized from 2,3,5,6-tetramethoxyphenyl acetate in a mixture of acetic anhydride and acetic acid. 1-[2-Hydroxy-3,5,6-trimethoxy-4-(methoxyinethoxy)phenyl]ethanone was cyclized to 7-hydroxy-5,6,8-trimethoxyflavone by using the Baker-Venkataraman transformation. The 7-benzyl ether of the flavone was oxidized with dimethyldioxirane and then treated with a small amount of p-toluenesulfonic acid to give 7-benzyloxy-3-hydroxy-5,6,8-trimethoxyflavone, which was converted into the methyl ether and tosylate. The 5-methoxy group in the methyl ether or tosylate was selectively cleaved with anhydrous aluminum bromide in acetonitrile under mild conditions to give the corresponding 5-hydroxyflavones and the latter compound with a 3-tosyloxy group was smoothly converted into the 3,5-dihydroxyflavone by hydrolysis with potassium carbonate in methanol. The hydrogenolysis of the 7-benzyloxy-3,5-dihydroxyflavone and its 3-methyl ether afforded quantitatively 3,5,7-trihydroxy-6,8-dimethoxyflavone and its 3-methyl ether. The process was suitable as a general method for synthesizing 3,5,7-trihydroxy-6,8-dimethoxyflavones and their 3-methyl ethers and the six flavones were synthesized for the clarification of their 1H and 13CNMR, MS, and UV spectral properties.