Synthesis and evaluation of α-hydroxy fatty acid-derived heterocyclic compounds with potential industrial interest

Abstract

The reaction of 2-hydroxyheptadecanoyl chloride (2) and anthranilic acid gave 2-(1-hydroxyheptadecyl)-4H-3,1-benzoxazin-4-one (3) which was used as starting material to synthesize some condensed and non-condensed heterocyclic compounds by a reaction with nitrogen nucleophiles (e.g., hydrazine hydrate, and formamide). The subsequent reaction of the synthetic products with different amounts of propylene oxide gave a novel group of nonionic compounds having a double function as antibacterial and surface active agents which may serve in the manufacturing of drugs, cosmetics, pesticides or as antibacterial and/or antifungal products. The surface active properties such as surface and interfacial tensions, cloud point, foaming height, wetting time, and emulsification power were determined. Antimicrobial and biodegradability were also screened.