Food and Fermentation Industries >

2023 , Vol. 49 >Issue 19: 152 - 159

DOI: https://doi.org/10.13995/j.cnki.11-1802/ts.033022

Improved synthesis and antioxidant activity of oxyresveratrol

  • CHEN Ying ,
  • ZHOU Hua ,
  • YAN Ri'an
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  • (College of Science and Engineering, Jinan University, Guangzhou 510632, China)

Received date: 2022-07-19

  Revised date: 2022-08-10

  Online published: 2023-11-01

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Abstract

The Wittig-Horner method used to prepare E-type olefins was applied in the total synthesis of oxyresveratrol. 2,3′,4,5′-tetramethoxystilbene intermediate was synthesized with cheap and easily available 3,5-dimethoxybenzyl alcohol and 2,4-dimethoxybenzaldehyde via bromination, Arbuzov rearrangement reaction, and Wittig-Horner reaction. Finally, the intermediate was demethylated with the help of aluminium trichloride, and then the target product oxyresveratrol was successfully prepared. The improved synthesis process had short synthetic steps, mild reaction conditions, easy operating processes, and a high yield. The structure of the final product was identified by melting point, infrared spectroscopy, mass spectrometry and nuclear magnetic resonance. The antioxidant activity of oxyresveratrol was discussed by ABTS radical scavenging activity,DPPH free radical, and ferric reducing antioxidant power with reference to vitamin C, butylated hydroxytoluene (BHT), and tert-butyl hydroquinone (TBHQ), and compared with piceatannol, resveratrol, and tea polyphenols for comparison. Results showed that oxyresveratrol had higher ABTS cation radical scavenging rate than that of vitamin C, BHT, and TBHQ, while its DPPH radical scavenging rate and ferric reducing antioxidant power were higher than that of resveratrol and BHT, showing excellent antioxidant power. These results will promote their application in food additives.

Key words： oxyresveratrol; Wittig-Horner reaction; synthesis; demethylation; antioxidant activity

Cite this article

CHEN Ying , ZHOU Hua , YAN Ri'an . Improved synthesis and antioxidant activity of oxyresveratrol[J]. Food and Fermentation Industries, 2023 , 49(19) : 152 -159 . DOI: 10.13995/j.cnki.11-1802/ts.033022

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