16280-26-5

Upstream product

• 1064-06-8 3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one 
• 74-88-4 methyl iodide 
• 108-24-7 acetic anhydride 
• 90-19-7 rhamnetin 
• 67-64-1 acetone 
• 143631-95-2 acetic acid 2-acetoxy-4-(3,5-diacetoxy-7-hydroxy-4-oxo-4H-chromen-2-yl)-phenyl ester 

Downstream Products

• 83170-21-2 3,3',5-Triacetoxy-4'-benzyloxy-7-methoxy-flavon 
• 83170-22-3 4'-Benzyloxy-3',5-dihydroxy-7-methoxy-flavon-3-O-octa-O-acetyl--β-D-galaktopyranosid 
• 69261-79-6 Rhamnetin-4'-benzylether 

Relevant academic research and scientific papers

Regioselective O-derivatization of quercetin via ester intermediates. An improved synthesis of rhamnetin and development of a new mitochondriotropic derivative

The regioselective synthesis of several quercetin (3,3',4',5,7-pentahydroxy flavone) tetraesters bearing a single free OH on 5-C was achieved in good yield by proper choice of reaction conditions using common esterification procedures. Tetracetylated quercetin with the free OH on 7-C was selectively obtained instead via imidazole-promoted deacylation of the corresponding pentaester. Unambiguous structural characterization of the two isomeric tetraacetyl quercetin derivatives was obtained by combined HSQC and HMBC 2D-NMR analysis. These molecules can be used as starting materials for the regioselective synthesis of other derivatives. High yield syntheses of the natural polyphenol rhamnetin (7-O-methylquercetin) and of the new mitochondriotropic compound 7-(4-triphenylphosphoniumbutyl) quercetin iodide are reported as examples.