Antioxidant activities of two novel synthetic methylbenzenediol derivatives

• Published in: Czech Journal of Food Sciences Vol. 32; no. 4; pp. 348 - 353
• Main Authors: Huang, Yan, Jiang, Zhiwu, Liao, Xianyan, Hou, Jianping, Weng, Xinchu
• Format: Journal Article
• Language: English; Czech; Slovak
• Published: Prague Czech Academy of Agricultural Sciences (CAAS) 01.01.2014; Czech Academy of Agricultural Sciences
• Subjects: 2-(tert-butyl)-5-methylbenzene-1,4-diol; 3-(tert-butyl)-5-methylbenzene-1,2-diol; Antioxidants; Benzene; Butanol; Chemical synthesis; dpph; Friedel-Crafts reaction; Hydrocarbons; Hydroxyl groups; Phenolic compounds; Phenols; Radicals; rancimat test; Scavenging; steric synergist effect; Synergistic effect
• ISSN: 1212-1800; 1805-9317
• DOI: 10.17221/283/2013-CJFS

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.