14787-34-9

Upstream product

• 100059-77-6 1-(2,6-dihydroxy-3,4-dimethoxy-phenyl)-2-methoxy-ethanone 
• 794-94-5 p-Methoxybenzoic anhydride 
• 27782-63-4 5,7-Dihydroxy-3,6-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 77-78-1 dimethyl sulfate 
• 14639-73-7 1-(3,6-dihydroxy-2,4-dimethoxy-phenyl)-2-methoxy-ethanone 
• 4472-73-5 3,5,6,7,4'-pentamethoxyflavone 

Downstream Products

• 4472-73-5 3,5,6,7,4'-pentamethoxyflavone 
• 50461-92-2 5,8-dihydroxy-3,4',6,7-tetramethoxyflavone 
• 124909-89-3 Toluene-4-sulfonic acid 3,6,7-trimethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-5-yl ester 
• 34170-18-8 3,5,6,7,8,4′-hexamethoxyflavone 
• 124909-96-2 Toluene-4-sulfonic acid 3-hydroxy-6,7-dimethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-5-yl ester 
• 4324-54-3 3,5-diacetoxy-6,7-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 4324-53-2 3,5-dihydroxy-6,7,4'-trimethoxyflavone 

Relevant academic research and scientific papers

Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae)

A series of 16 flavonoids were isolated and prepared from bud exudate of Gardenia urvillei and Gardenia oudiepe, endemic to New Caledonia. Most of them are rare polymethoxylated flavones. Some of these compounds showed noticeable activity against Leishmania (Leishmania) amazonensis, Plasmodium falciparum and Trypanosoma brucei gambiense, in addition to tubulin polymerization inhibition at low micromolar concentration. We also provide a full set of NMR data as some of the flavones were incompletely described.

STUDIES OF THE SELECTIVE O-ALKYLATION AND DEALKYLATION OF FLAVONOIDS. XII. A NEW, CONVENIENT METHOD FOR SYNTHESIZING 3,5-DIHYDROXY-6,7-DIMETHOXYFLAVONES FROM 3,5,6,7-TETRAMETHOXYFLAVONES

The 5-methoxy group on 3,5,6,7-tetramethoxyflavones and the 3-methoxy group on 3,6,7-trimethoxy-5-tosyloxy-flavones were selectively cleaved with anhydrous aluminum bromide in acetonitrile under controlled conditions without the cleavage of benzyloxy groups on the B ring.By the application of these reactions, seven 3,5-dihydroxy-6,7-dimethoxyflavones were easily synthesized from the corresponding 3,5,6,7-tetramethoxyflavones which were synthesized from 3,6-dihydroxy-2,4ω-trimethoxycetophenone by means of the Allan-Robinson reaction followed by methylation.Keywords: Allan-Robinson reaction ; selective demethylation; 3,5,6,7-tetramethoxyflavone; 5-hydroxy-3,6,7-trimethoxyflavone; 6-hydroxy-3,5,7-trimethoxyflavone; 5-tosyloxyflavone; 5,6-dihydroxy-3,7-dimethoxyflavone; 3,5-dihydroxy-6,7-dimethoxyflavone, 3,5-diacetoxy-6,7-dimethoxyflavone

Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. 10. Selective Demethylation of 7-Hydroxy-3,5,8-trimethoxyflavones with Anhydrous Aluminum Halide in Acetonitrile or Ether

Demethylation of five 7-hydroxy-3,5,8-trimethoxyflavones and their acetates with anhydrous aluminum halides in acetonitrile or ether was studied and the following results were found. (1) The demethylation was apparently influenced by both solvents and afforded 5,7-dihydroxy-3,8-dimethoxyflavones in acetonitrile and 3,7-dihydroxy-5,8-dimethoxyflavones in ether as main products. (2) The demethylation with 5percent w/v anhydrous aluminum bromide in acetonitrile procedeed quantitatively to give a mixture of corresponding 5- and 3-hydroxyflavones, but that of 7-hydroxy-3,4',5,8-tetramethoxyflavone and its acetate with 10percent anhydrous aluminum chloride in acetonitrile afforded 6-acetyl-5,7-dihydroxy-3,4,8-trimethoxyflavone as a byproduct along with the 5- and 3-hydroxyflavones. (3) The demethylation of the acetates proceeded more smoothly than that of hydroxyflavones and was superior to that of the flavones with a hydroxy group. (4) These demethylations are available for the syntheses of 3- or 5-hydroxyflavones with no substituent at 6-position.