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College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, China
Author to whom correspondence should be addressed.
Molbank 2010, 2010(4), M703;
Submission received: 13 September 2010 / Accepted: 20 October 2010 / Published: 27 October 2010


A new quercetin derivative, 3,5-di(-O-acetyl)-3′,4′,7-tri[-O-(2-O-acetylethyl)]-quercetin, was synthesized. The structure of the target compound was characterized by IR, 1H NMR, 13C NMR and MS.

Graphical Abstract

1. Introduction

Quercetin (3,3',4',5,7-pentahydroxyflavone) and its derivatives have a wide range of biological activity, such as antioxidant [1,2,3,4], anticarcinogenesis [5,6,7,8,9,10], vasodilatation [11,12,13], inhibition of various enzymes [14,15,16], UV-shielding properties [17,18], etc. Troxerutin (trihydroxy-ethylrutoside), which serves as a drug, is known as a radical scavenger with antioxidant effects, so that treatment with it increases the healing of capillary endothelial defects [19]. Thus, the synthesis of quercetin derivatives is of considerable importance. For instance, modifications can increase fat-solubility and stability of the molecule. The compound may be useful as an intermediate to synthesize other relevant compounds. Here, we would like to report a convenient procedure for the preparation of 3,5-di(-O-acetyl)- 3′,4′,7-tri[-O-(2-O-acetylethyl)]quercetin.

2. Structural Characterization

1H NMR (Bruker 300 MHz, CDCl3): δH 7.45 (d, J = 9.0 Hz, 1 H, 6′-H), 7.40 (s, 1 H, 2′-H), 7.00 (d, J = 9.0 Hz, 1 H, 5′-H), 6.87 (s, 1 H, 8-H), 6.65 (s, 1 H, 5-H), 4.46 (s, 6 H, 3 × OCH2), 4.27 (s, 6 H, 3 × OCH2 ), 2.42 (s, 3 H, COCH3 ), 2.31 (s, 3 H, COCH3 ), 2.10 (s, 9 H, 3 × COCH3) ppm. 13C NMR (75 MHz, CDCl3): 170.85, 170.76, 169.99, 169.44, 167.86, 162.45, 157.96, 154.38, 151.42, 150.82, 148.50, 133.27, 123.12, 122.96, 115.35, 114.17, 111.36, 108.83, 99.52, 67.93, 67.26, 66.75, 62.71, 62.53, 62.08, 21.05, 20.77, 20.58 ppm. IR (Bruker Tensor 27, KBr): 3453, 1760, 1636, 1384 cm−1. ESI-MS: m/z 645.6 (M+ +1). Elemental Anal. (Perkin Elmer PE 2400 II CHNS/O): calcd for C31H32O15 (644.59): C, 57.76; H, 5.00; O, 37.23. Found: C, 57.8; H, 5.0; O, 37.2.

3. Experimental

Ethylene oxide (6.60 g, 150 mmol) was added dropwise over a period of 6 h to a mixture of rutin (12.21 g, 20 mmol) and NaOH (0.28 g, 7 mmol) in 100 mL of H2O with continuous stirring at 75 °C. The pH value of the mixture was adjusted to 4.0 by concentrated hydrochloric acid, then the yellow solid that was formed was collected by filtration, washed with cold water, and dried under vacuum to give compound 1. The purity was sufficient for use in the next step.
A mixture of compound 1 (7.42 g, 10 mmol) and H2SO4 (1%, 500 mL) was stirred under reflux for 2 h (reaction progress was checked by TLC). After cooling, the pH value of the mixture was adjusted to 4.5 by sodium hydroxide solution, then the yellow solid that was formed was collected by filtration, washed with cold water, and dried under vacuum to give compound 2.
To a mixture of compound 2 (2.17 g, 5 mmol) and acetic anhydride (50 mL, 530 mmol) was added H2SO4 (93%, 5 drops), and the mixture was stirred at room temperature for 24 h (reaction progress was checked by TLC). The precipitate was collected by filtration, washed with cold water, and recrys-tallized from EtOH/H2O to give 2.10 g (65.2%) of compound 3 as white powder, m.p. 95.9–97.2 °C.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3


The authors are grateful to Zhixian Liu and Lixin Yu for determinations of NMR, IR and elemental analysis.


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Scheme 1. Synthesis of 3,5-di(-O-acetyl)-3′,4′,7-tri[-O-(2-O-acetylethyl)]quercetin.
Scheme 1. Synthesis of 3,5-di(-O-acetyl)-3′,4′,7-tri[-O-(2-O-acetylethyl)]quercetin.
Molbank 2010 m703 sch001

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MDPI and ACS Style

Liu, Y.; Zhang, L. 3,5-Di(-O-acetyl)-3′,4′,7-tri[-O-(2-O-acetylethyl)]quercetin. Molbank 2010, 2010, M703.

AMA Style

Liu Y, Zhang L. 3,5-Di(-O-acetyl)-3′,4′,7-tri[-O-(2-O-acetylethyl)]quercetin. Molbank. 2010; 2010(4):M703.

Chicago/Turabian Style

Liu, Yufa, and Liwei Zhang. 2010. "3,5-Di(-O-acetyl)-3′,4′,7-tri[-O-(2-O-acetylethyl)]quercetin" Molbank 2010, no. 4: M703.

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