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Corynomycolic acids have two hydrophilic heads (OH and COOH) and two hydrophobic tails on adjacent carbon atoms. In this work, hybrid type corynomycolic acids ( syn - and  anti -isomers) were synthesized via the following three steps: 1) crossed Claisen condensation of  t -butyl tridecanoate with ethyl per fluorooctanoate, 2) reduction of C = O to OH, and 3) conversion of COO- t -Bu to COOH using CF 3 COOH. Both hydrophilic groups (OH and COOH) of hybrid corynomycolic acid would dissociate to –O –  and –COO –  at alkaline condition ( p H = 12) while they remain unchanged at acidic condition ( p H &lt; 3). The effect of hybrid structure on the surfactant properties was investigated by the surface tension and surface pressure-area (π- A ) measurements. Hybrid type corynomycolic acid gave smaller cmc and γ cmc  than dialkyl type one due to fluoroalkyl chain. With respect to the stereochemistry, the  anti -isomer attained a smaller γ cmc  value than the  syn -isomer. In π- A  measurements, the monolayer of the  syn -isomer showed a lower collapsing pressure (∼15 mN m –  1 ) than that of the  anti -isomer.

Hybrid Biosurfactant: Syntheses of Hybrid Corynomycolic Acid and its Monolayer Formation