Event Title

Synthesis of oxobutanoate-substituted carvacrol and thymol derivatives as potential antibacterial agents

Presenter Information

Allison Graybill

Faculty Advisor

Dr. Geneive Henry

Start Date

24-4-2018 5:00 PM

End Date

24-4-2018 6:00 PM

Description

The major components of oregano oil are the isomeric phenols, carvacrol and thymol. These phenols have a wide range of biological activities including anticancer, antibacterial, and insecticidal properties. Previous studies have shown that conversion of carvacrol and thymol to their corresponding ester and carbamate derivatives led to retention or enhancement of antibacterial activity. In the current study, fourteen oxobutanoate derivatives of ethyl carvacrol and ethyl thymol have been prepared for evaluation of their antibacterial effects against clinically isolated Staphylococcus aureus strains. Ethyl carvacrol and ethyl thymol were prepared by the Williamson ether synthesis. The oxobutanoic acid moiety was introduced to the carvacrol/thymol core via Friedel-Crafts acylation, followed by alkylation to afford the carvacrol/thymol-oxobutanoates. The synthesized compounds were obtained in good yield and characterized by NMR spectroscopy.

This document is currently not available here.

Share

COinS
 
Apr 24th, 5:00 PM Apr 24th, 6:00 PM

Synthesis of oxobutanoate-substituted carvacrol and thymol derivatives as potential antibacterial agents

The major components of oregano oil are the isomeric phenols, carvacrol and thymol. These phenols have a wide range of biological activities including anticancer, antibacterial, and insecticidal properties. Previous studies have shown that conversion of carvacrol and thymol to their corresponding ester and carbamate derivatives led to retention or enhancement of antibacterial activity. In the current study, fourteen oxobutanoate derivatives of ethyl carvacrol and ethyl thymol have been prepared for evaluation of their antibacterial effects against clinically isolated Staphylococcus aureus strains. Ethyl carvacrol and ethyl thymol were prepared by the Williamson ether synthesis. The oxobutanoic acid moiety was introduced to the carvacrol/thymol core via Friedel-Crafts acylation, followed by alkylation to afford the carvacrol/thymol-oxobutanoates. The synthesized compounds were obtained in good yield and characterized by NMR spectroscopy.