Compounds with antioxidant properties can scavenge free radicals such as reactive oxygen species that damage biological macromolecules. The damage that free radicals create are related to the progression of many diseases including cancer, diabetes, neurodegenerative disorders, and cardiovascular diseases. Phenolic compounds are often able to act as antioxidants because the phenoxy radicals that form when they scavenge the free radicals are resonance stabilized. Extending the conjugation of the phenolic ring could possibly increase the compound’s antioxidant capacity. To test this hypothesis, derivatives of both thymol and eugenol were synthesized and assessed for their antioxidant properties. The compounds synthesized were 4-chloro-2-isopropyl-5-methylphenol, 2-(allyloxy)-1-isopropyl-4-methylbenzene, and 4-allyl-2-chloro-6-methoxy-phenol. These compounds were synthesized by reacting either thymol or eugenol with lithium chloride, copper chloride, and acetic acid to chlorinate both compounds. Also, thymol was reacted with allyl bromide in sodium hydroxide to add an allyl group to thymol. The synthesized compounds were analyzed using GC-MS, H NMR, and C NMR. Their antioxidant properties were then assessed by using a DPPH radical scavenging assay and a hydrogen peroxide scavenging assay. By analyzing the antioxidant capacities of the compounds, it could be determined if the phenolic compounds with extended conjugation have improved antioxidant capacities.

Antioxidant properties of thymol and eugenol derivatives

2019 Spring National Meeting

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