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<i>C</i>-tetra(4-methoxyphenyl)calix[4]resorcinarene was synthesized by hydrochloric acid-catalysed cyclocondensation of resorcinol and 4-methoxybenzaldehyde. Under these conditions, the reaction produces a conformational mixture of <i>crown</i> and <i>chair</i> structural conformers, which were separated and characterized by chromatographic and spectroscopic techniques. The antioxidant activity of both conformers was measured by using the DPPH assay, through which it was observed that the <i>chair</i> conformer showed greater antioxidant activity (IC₅₀ = 47.46 ppm) than the <i>crown</i> conformer (IC₅₀ = 78.46 ppm). Additionally, it was observed that the mixture of both conformers presented lower antioxidant activity than either conformer in isolation. The results found suggest that the <i>chair</i> conformer has efficient antioxidant activity that makes it a potential target for further research.