Mixture of fatty acids obtained from coconut, palm kernel, palm, jatropha, karanja, Sterculia foetida, and high oleic sunflower oils were used for the preparation of sodium N-acyl isoleucines (NaNAIle) via Schotten-Baumann reaction except castor oil which was prepared in thermal condensation in good yields. The products were characterized by chromatographic and spectral techniques. Surface active properties such as surface tension, wetting, foaming characteristics, emulsion stability, calcium tolerance, and micellization properties were evaluated for all the synthesized products. The results showed that all the products exhibited superior surface active properties like critical micelle concentration (CMC) and emulsion stability when compared to the commercial surfactant, sodium lauryl sulphate (SLS). The NaNAIle also exhibited promising cytotoxicity against human cancer cell lines except 3 and 5. 5, 6, and 8 showed antimicrobial activity against Gram-positive and Gram-negative bacteria. 1, 2, 7, and 8 exhibited good antioxidant properties.
Synthesized sodium N-pamitoyl amino acids were evaluated for surface and antimicrobial properties and compared with sodium lauryl sulphate (SLS). Emulsion stability of the amino acid surfactants and calcium tolerance of the sodium N-palmitoyl isoleucine were better as compared to SLS. Wetting ability and foaming properties of the palmitic acidbased surfactants were inferior to SLS. N-Acyl amino acids exhibited better antibacterial activity compared to sodium salts of N-acyl amino acids and standard compounds against S. aureus MLS-16 and Bacillus subtilis. These studies revealed that the palmitoyl amino acid surfactants can be exploited in household, skin care formulations and industrial applications.
Sodium N-acyl phenylalanines (NaNAPhe) were synthesized using mixture of fatty acids obtained from coconut, palm, karanja, Sterculia foetida and high oleic sunflower oils via Schotten-Baumann reaction in 60-78% yields to see the influence of hydrophobic group of fatty acyl group functionality with head group phenylalanine on their surface active properties. The products were characterized by chromatographic (TLC, column, GC) and spectral techniques (IR, NMR, Mass). The synthesized products were evaluated for their surface active properties such as surface tension, wetting power, foaming characteristics, emulsion stability, calcium tolerance, critical micelle concentration (CMC) and thermodynamic properties. The results showed that all the products exhibited superior surface active properties like critical micelle concentration (CMC, 0.018-0.00041 mmol/L), calcium tolerance (26.5-65.8 ppm) and emulsion stability (262-844 s) compared to reference sodium lauryl sulphate (SLS). All the sodium Nacyl phenylalanines except sodium N-coconut fatty acyl phenylalanines exhibited promising cytotoxicity against human cancer cell lines. These new vegetable oilbased surfactants have potential in personal care, pharmaceutical and industrial applications.
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