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

Type
Label
  • Regioselective O-derivatization of quercetin via ester intermediates. An improved synthesis of rhamnetin and development of a new mitochondriotropic derivative. (Articolo in rivista) (literal)
Anno
  • 2010-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.3390/molecules15074722 (literal)
Alternative label
  • Mattarei A; L. Biasutto; F. Rastrelli; S. Garbisa; E. Marotta; M. Zoratti; C. Paradisi. (2010)
    Regioselective O-derivatization of quercetin via ester intermediates. An improved synthesis of rhamnetin and development of a new mitochondriotropic derivative.
    in Molecules (Basel, Online)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Mattarei A; L. Biasutto; F. Rastrelli; S. Garbisa; E. Marotta; M. Zoratti; C. Paradisi. (literal)
Pagina inizio
  • 4722 (literal)
Pagina fine
  • 4736 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 15 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 15 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 7 (literal)
Note
  • PubMe (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Mattarei A; Rastrelli F; Marotta E; Paradisi C: Dip. di Scienze Chimiche, Università di Padova. Biasutto L; Garbisa S; Zoratti M: Dip. di Scienze Biomediche Sperimentali, Università di Padova. Zoratti M: IN - Padova (literal)
Titolo
  • Regioselective O-derivatization of quercetin via ester intermediates. An improved synthesis of rhamnetin and development of a new mitochondriotropic derivative. (literal)
Abstract
  • 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. (literal)
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