Pathogenic microorganisms are a threat to human health since they can cause severe infectious diseases, and to inactivate these pathogens, numerous antimicrobial agents have been developed. This presentation focuses on a new class of ethyl phenolic branched chain fatty acid arginate products derived from natural reagents such as arginine, phenolic and fatty acid. The products can be prepared in four steps starting with the phenolic branched chain fatty acid material. This multistep synthesis is found to be general and can be applied to any type of fatty acids including iso-oleic acid. All intermediates and desired products can be characterized by attenuated total reflectance fourier transform infrared, mass spectrometry, and nuclear magnetic resonance. From the micro-dilution method, these ethyl phenolic fatty acid arginate products are active against Gram-positive bacteria with the minimum inhibitory concentration and minimum bactericidal concentration slightly better than commercial ethyl lauroyl arginate. The enhanced bioactive properties come from the hydroxyl functional group on the aromatic ring as it improves the hydrophilicity of the fatty acid.  These compounds are also found to have superior ability in lowering the surface tension than the commercial product, which can be developed into antimicrobial surfactants for applications in foods, cleaners, and coatings.

New ethyl phenolic branched chain fatty acid arginate products with antimicrobial and surfactant properties

ACS Spring 2022

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