Czech J. Food Sci., 2014, 32(4):348-353 | DOI: 10.17221/283/2013-CJFS

Antioxidant activities of two novel synthetic methylbenzenediol derivativesOriginal Paper

Yan Huang1, Zhiwu Jiang1, Xianyan Liao1, Jianping Hou2, Xinchu Weng1
1 School of Life Science, Shanghai University, Shanghai, P.R. China
2 State Key Laboratory of Dairy Biotechnology, Technology Center of Bright Dairy and Food Co. Ltd., Shanghai, P.R. China

2-(tert-Butyl)-5-methylbenzene-1,4-diol and 3-(tert-butyl)-5-methylbenzene-1,2-diol were synthesised by Friedel-Craft reaction of 2-methylbenzene-1,4-diol and 4-methylbenzene-1,2-diol, respectively, with tertiary butanol providing reasonable yields. The antioxidant activities of these two products, mother compounds and 2-(tert-butyl)benzene-1,4-diol were investigated and compared by means of 2,2-diphenyl-1-picrylhydrazyl radical and Rancim at test; 3-(tert-butyl)-5-methylbenzene-1,2-diol is the most potent antioxidant tested by using Rancimat test experiment. The 2,2-diphenyl-1-picrylhydrazyl radical scavenging abilities of 2-methylbenzene-1,4-diol, 4-methylbenzene-1,2-diol and 2-(tert-butyl)benzene-1,4-diol are almost equal and more than twice as strong as 2-(tert-butyl)-5-methylbenzene-1,4-diol and 3-(tert-butyl)-5-methylbenzene-1,2-diol. The antioxidant activities of the five compounds evaluated by Rancimat test mainly depend on their steric synergist effects between the two phenolic hydroxyl groups in their molecules. The antioxidant activities of the five compounds mainly depend on how many 2,2-diphenyl-1-picrylhydrazyl radicals can be scavenged by one mole of them in 2,2-diphenyl-1-picrylhydrazyl test. One mole of 2-methylbenzene-1,4-diol, 4-methylbenzene-1,2-diol and 2-(tert-butyl)benzene-1,4-diol can scavenge four moles of 2,2-diphenyl-1-picrylhydrazyl radicals, but one mole of 2-(tert-butyl)-5-methylbenzene-1,4-diol or 3-(tert-butyl)-5-methylbenzene-1,2-diol can only scavenge two mole 2,2-diphenyl-1-picrylhydrazyl radicals because 2,2-diphenyl-1-picrylhydrazyl radicals are very bulky.

Keywords: 2-(tert-butyl)-5-methylbenzene-1,4-diol; 3-(tert-butyl)-5-methylbenzene-1,2-diol; steric synergist effect; DPPH; Rancimat test

Published: August 31, 2014  Show citation

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Huang Y, Jiang Z, Liao X, Hou J, Weng X. Antioxidant activities of two novel synthetic methylbenzenediol derivatives. Czech J. Food Sci. 2014;32(4):348-353. doi: 10.17221/283/2013-CJFS.
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