1, 2, 3, 5, 6, 7-六羟基-9, 10-蒽醌的合成及其抗氧化活性研究

doi:10.3969/j.issn.0253-2417.2022.06.009

Abstract

Abstract:

1, 2, 3, 5, 6, 7-hexahydroxy-9, 10-anthraquinone was synthesized by Friedel-Crafts acylation reaction using gallic acid as raw material and methanesulfonic acid as catalyst. The structure of the target product was verified by ultraviolet-visible(UV-vis) spectroscopy, Fourier transform infrared(FT-IR) spectroscopy, nuclear magnetic resonance(NMR) spectroscopy, and liquid chromatography-mass spectrometry(LC-MS) spectroscopy. The antioxidant activities in vitro of hexahydroxy-anthraquinone were evaluated in terms of its scavenging abilities on ABTS radical (ABTS⁺·), DPPH radical(DPPH·) and superoxide anion radical (O₂^-·). The results showed that the molar absorbance coefficient(ε_λmax) of 1, 2, 3, 5, 6, 7-hexahydroxy-9, 10-anthraquinone at the maximum absorption wavelength of 293 nm was 3.25×10⁴ L/(cm·mol), which was two times higher than that of the commonly used UV absorber 4-methoxycinnamic acid-2-ethylhexyl ester(OMC), indicating that it was an excellent UV absorber in UVB band. The half-inhibitory concentrations(IC₅₀) of hexahydroxy-anthraquinone for the scavenging of ABTS⁺·, DPPH·, and O₂^-· were 42.1, 39.4, and 30.8 μmol/L, respectively. The scavenging ability of it on ABTS⁺· and DPPH· was stronger than that of Vc, but weaker than that of gallic acid, and the scavenging ability of it on O₂^-· was stronger than those of Vc and gallic acid.

Key words: Friedel-Crafts reaction, gallic acid, 1, 2, 3, 5, 6, 7-hexahydroxy-9, 10-anthraquinone, antioxidant activity in vitro, UV-absorber

CLC Number:

TQ35
TQ244.6

Xiang LEI, Minfeng ZHANG, Kexin HU, Yu KE, Deyong ZHENG. Synthesis and Antioxidant Activity of 1, 2, 3, 5, 6, 7-Hexahydroxy-9, 10-Anthraquinone[J]. Chemistry and Industry of Forest Products, 2022, 42(6): 64-68.

Figures/Tables 4

References 24

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Synthesis and Antioxidant Activity of 1, 2, 3, 5, 6, 7-Hexahydroxy-9, 10-Anthraquinone

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