Event Title

Synthesis and Antioxidant Evaluation of Thioether Derivatives of Carvacrol

Faculty Advisor

Dr. Geneive Henry

Start Date

23-4-2019 12:00 PM

End Date

23-4-2019 1:00 PM

Description

Carvacrol is an essential oil of oregano that has been proven to contain antibacterial, anticancer, and antioxidant capacities. Starting with carvacrol, synthetic reactions were conducted to form thioether derivatives. A Williamson ether synthesis was used to attach a methyl group onto the carvacrol compound, which was followed up by an attachment of a chloroacetophenone group via a Friedel-Craft acylation. Starting with methylcarvacrol chloroacetophenone, analogues with the addition benzoxazole, benzimidazole, benzthiazole, and oxadiazole were synthesized in yields ranging from 27%-97%. The methylcarvacrol derivatives were purified using column chromatography and characterized NMR and IR spectroscopy. CUPRAC assays were conducted containing select methylcarvacrol analogues, which had their antioxidant capacities tested versus Trolox, a known antioxidant. Results showed analogues had TEAC ratios above 1.00 proving to be more effective than Trolox. Carvacrol showed the highest TEAC ratio of 1.96, as methylcarvacrol picolinic oxadiazole was the highest derivative with a TEAC ratio of 1.94.

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Apr 23rd, 12:00 PM Apr 23rd, 1:00 PM

Synthesis and Antioxidant Evaluation of Thioether Derivatives of Carvacrol

Carvacrol is an essential oil of oregano that has been proven to contain antibacterial, anticancer, and antioxidant capacities. Starting with carvacrol, synthetic reactions were conducted to form thioether derivatives. A Williamson ether synthesis was used to attach a methyl group onto the carvacrol compound, which was followed up by an attachment of a chloroacetophenone group via a Friedel-Craft acylation. Starting with methylcarvacrol chloroacetophenone, analogues with the addition benzoxazole, benzimidazole, benzthiazole, and oxadiazole were synthesized in yields ranging from 27%-97%. The methylcarvacrol derivatives were purified using column chromatography and characterized NMR and IR spectroscopy. CUPRAC assays were conducted containing select methylcarvacrol analogues, which had their antioxidant capacities tested versus Trolox, a known antioxidant. Results showed analogues had TEAC ratios above 1.00 proving to be more effective than Trolox. Carvacrol showed the highest TEAC ratio of 1.96, as methylcarvacrol picolinic oxadiazole was the highest derivative with a TEAC ratio of 1.94.