73213-66-8

Upstream product

• 56002-84-7 2,3,5,6-tetramethoxyphenyl acetate 
• 13698-23-2 apigenin 4',5-dimethyl ether 
• 17306-46-6 rhoifolin 
• 124-41-4 sodium methylate 
• 176662-05-8 2-benzyloxy-3,4,6-trimethoxyphenyl acetate 
• 176662-06-9 1-(2,4-diacetoxy-3,5,6-trimethoxyphenyl)ethanone 
• 56002-85-8 1-benzyloxy-2,3,5,6-tetramethoxybenzene 
• 176662-07-0 1-(2-Hydroxy-3,5,6-trimethoxy-4-methoxymethoxy-phenyl)-ethanone 
• 56002-83-6 2,3,5,6-tetramethoxyphenol 
• 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 
• 1026851-49-9 1-(2-Hydroxy-3,5,6-trimethoxy-4-methoxymethoxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione 

Downstream Products

• 10176-76-8 7-Benzyloxy-5,6,8-trimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 481-53-8 tangeritin 
• 50461-91-1 3-hydroxy-5,6,7,8,4′-pentamethoxyflavone 
• 34170-18-8 3,5,6,7,8,4′-hexamethoxyflavone 
• 50439-46-8 5-hydroxy-3,6,7,8,4′-pentamethoxyflavone 
• 2798-20-1 gardenin B 
• 1026339-87-6 Toluene-4-sulfonic acid 7-benzyloxy-5,6,8-trimethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl ester 
• 176662-33-2 7-Benzyloxy-5-hydroxy-3,6,8-trimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 176662-13-8 7-Benzyloxy-3-hydroxy-5,6,8-trimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 176662-27-4 7-Benzyloxy-3,5-dihydroxy-6,8-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 50461-86-4 5,7-dihydroxy-3,6,8,4′-tetramethoxyflavone 
• 50461-98-8 7-benzyloxy-3,5,6,8-tetramethoxy-2-(4-methoxy-phenyl)-chromen-4-one 

Relevant academic research and scientific papers

Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells

Abstract: A series of polymethoxyflavonoids (3–16) were synthesized through dehydrogenation, O-methylation, glycoside hydrolysis, bromination, microwave-assisted aromatic nucleophilic substitution, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. All the synthetic compounds were test for antiproliferative activities on human cervical carcinoma Hela cell line by the standard CCK-8 assay, the result showed that most of the target compounds exhibited moderate to potent antiproliferative activities on Hela cells comparable with the positive control cis-Platin. Among them, 5-hydroxypolymethoxy flavonoid 13 showed the strongest activity (IC50 0.791 μM). Graphical Abstract: [InlineMediaObject not available: see fulltext.].

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.