Synthesis Of 1, 4-dipalmitoyl Hydroxyproline

1,4-dipalmitoyl hydroxyproline, plant-derived lipid agent consisting of hydroxyproline (natural amino acid) & palmitic acid, is anti-aging agent which can be applied to cosmetics. This experiment focused on the synthesis of 1,4-dipalmitoyl hydroxyproline by Schotten Banmamm condensation reactions, and studied the non-aqueous enzyme catalysis.1.Firstly, palmitoyl chloride used in esterification and amidation, By studying of the influencing facts such as molar ratio of materials, the time, temperature in detail, the optimum reaction conditions were obtained as follows: molar ratio of materials was 1:2, reaction temperature was 70-80℃, reaction time was 3 h.2.1,4-dipalmitoyl hydroxyproline was obtained by Schotten Banmamm condensation reactions. The different influencing factors of reaction were studied. Then the reaction conditions were obtained as follows: volume ratio of acetone was 50%, molar ratio of materials was 1:2.5, pH=8~9, reaction temperature was 15℃, reaction time was 4 h. The conversion of reaction had reached to 98.13 % under the optimal conditions, and the yield 60%. Orthogonal design and Response surface methodology were used in the experiment for optimum condition. The experimental results show that the molar ratio of materials had the largest effect, the second was reaction temperature, third was volume ratio of acetone and reaction time had the least effect. And the optimum reaction conditions were obtained as follows: volume ratio of acetone was 55%, molar ratio of materials was 1:2.5, reaction temperature was 15℃, reaction time was 5 h. By using the three-level-three-factor response surface methodology, a quadratic polynomial mathematical model was established. The influences of the reaction temperature, volume ratio of organic agent and the molar ratio of materials were investigated by determining the yield as the response. The optimum reaction conditions were obtained as follows: volume ratio of acetone was 55%, reaction temperature was 15℃, molar ratio of materials was 2.5. And in these conditions, the yield reaches 58.26%.3.In order to study the non-aqueous enzyme catalysis, the influencing factors were investigated. The results show that the catalysis effects of Lipolase lipase and Savinase albuminuria are better than others; Conversion of reaction, much bigger in isooctane, will increase by adding of enzyme. And the optimum water content is 1~2%.