Next Article in Journal
Synthesis and Preliminary Evaluation of the Antimicrobial Activity of Selected 3-Benzofurancarboxylic Acid Derivatives
Next Article in Special Issue
Chalcones and Dihydrochalcones Augment TRAIL-Mediated Apoptosis in Prostate Cancer Cells
Previous Article in Journal
Synthesis of Some New Pyridine-2,6-carboxamide-derived Schiff Bases as Potential Antimicrobial Agents
Previous Article in Special Issue
Phenolic Extracts from Acacia mangium Bark and Their Antioxidant Activities
Molecules 2010, 15(7), 4722-4736; doi:10.3390/molecules15074722
Article

Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative

1, 2, 1, 2, 1, 2,3 and 1,*
Received: 10 June 2010 / Revised: 22 June 2010 / Accepted: 2 July 2010 / Published: 6 July 2010
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Download PDF [328 KB, uploaded 18 June 2014]

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.
Keywords: regioselective alkylation; mitochondrial targeting; quercetin; rhamnetin; polyphenols regioselective alkylation; mitochondrial targeting; quercetin; rhamnetin; polyphenols
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

Mattarei, A.; Biasutto, L.; Rastrelli, F.; Garbisa, S.; Marotta, E.; Zoratti, M.; Paradisi, C. Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative. Molecules 2010, 15, 4722-4736.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert