Journal
MOLECULES
Volume 15, Issue 7, Pages 4722-4736Publisher
MDPI
DOI: 10.3390/molecules15074722
Keywords
regioselective alkylation; mitochondrial targeting; quercetin; rhamnetin; polyphenols
Funding
- University of Padova (Progetti d'Ateneo)
- Fondazione Cassa di Risparmio di Padova e Rovigo (Progetti d'Eccellenza)
- University of Padova (Assegno di Ricerca)
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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.
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