50461-91-1

Upstream product

• 13698-23-2 apigenin 4',5-dimethyl ether 
• 17306-46-6 rhoifolin 
• 73213-66-8 7-hydroxy-5,6,8,4′-tetramethoxyflavone 
• 481-53-8 tangeritin 
• 173217-39-5 Toluene-4-sulfonic acid 5,7,8-trimethoxy-6-methoxymethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl ester 
• 173217-40-8 Toluene-4-sulfonic acid 6-hydroxy-5,7,8-trimethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl ester 
• 1027152-43-7 4-Methoxy-benzoic acid 2-acetyl-3,5,6-trimethoxy-4-methoxymethoxy-phenyl ester 
• 173217-35-1 5,7,8-Trimethoxy-6-methoxymethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 169130-15-8 6-hydroxy-4',5,7,8-tetramethoxyflavone 
• 55742-65-9 2',5'-dihydroxy-3',4',6'-trimethoxyacetophenone 
• 173217-41-9 Toluene-4-sulfonic acid 5,6,7,8-tetramethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl ester 

Downstream Products

• 34170-18-8 3,5,6,7,8,4′-hexamethoxyflavone 
• 50439-46-8 5-hydroxy-3,6,7,8,4′-pentamethoxyflavone 

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.].

Semisynthesis of polymethoxyflavonoids from naringin and hesperidin

Polymethoxyflavonoids (PMFs) possess important biological activities, notably as anticancer agents. Semisynthesis of a series of PMFs were performed by glycoside hydrolysis, dehydrogenation, bromination, aromatic nucleophilic substitution, O-methylation, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. A new synthetic method for selective methylation using CuBr catalysed and microwave-assisted reaction was developed, and the dimethyl dioxirane oxidation of flavones to flavonols was much improved. The new semisynthetic route has the advantages of easy availability of starting materials, simple operation and good yields.

Studies of the selective O-alkylation and dealkylation of flavonoids. XIX. A convenient method for synthesizing 3,5,6,7,8-pentaoxygenated flavones

The methoxymethyl ethers of 6-hydroxy-5,7,8-trimethoxyflavones, which were derived from 2',5'dihydroxy-3',4',6'-trimethoxyacetophenone, were oxidized with dimethyldioxirane to give the corresponding 3-hydroxyflavones. Selective O-alkylation and dealkylation of the 3-hydroxyflavones were examined and a convenient method for synthesizing the following ten kinds of 3,5,6,7,8- pentaoxygenated flavones was established: 3-hydroxy-5,6,7,8- tetramethoxyflavones, 3,5-dihydroxy-6,7,8-trimethoxyflavones, 3,6-dihydroxy- 5,7,8-trimethoxyflavones, 3,5,6-trihydroxy-7,8-dimethoxyflavones, 3,5,6,7- tetrahydroxy-8-methoxyflavones, and their 3-methyl ethers. Furthermore, 3,5,8-trihydroxy-4',6,7-trimethoxyflavone, 3,8-dihydroxy-4',5,6,7- tetramethoxyflavone, and 5,8-dihydroxy-3,6,7-trimethoxyflavones were similarly synthesized and their spectral properties were examined. Additionally, the proposed structures of three natural flavones were revised.