Florent Yvergnaux

Separation of glyceride positional isomers by silver ion chromatography

Separation of triglyceride and diglyceride positional isomers by silver ion high-performance liquid chromatography coupled with an evaporative light-scattering detector is described. The triglyceride isomers had a fatty acid composition of CLC and CCL, where C and L were caprylic acid and linoleic acid, respectively. Diglyceride isomers, 1,2(2,3)-diglyceride and 1,3-diglyceride, which contained caprylic acid were separated too. A solvent system based on n-hexane, 2-propanol, ethyl acetate, and acetonitrile with a flow-rate of 0.8 ml/min was developed. Calibration curves of CLC and CCL were achieved with triolein as internal standard. Using this method, the incorporation of linoleic acid onto specific a position of glycerol backbone can be monitored.

Evaluation of regioselectivity of lipases based on synthesis reaction conducted with propyl alcohol, isopropyl alcohol and propylene glycol

Preliminary investigations on the regioselectiviy of various lipases were performed. Ten commercial lipases from different origins, including three immobilized lipases, were tested by esterification reaction between caprylic acid and propyl or isopropyl alcohol in n-hexane. Reaction products were analyzed with a gas chromatograph. Best yields were obtained with immobilized lipase IM60 from Rhizomucor miehei. Therefore, this enzyme was chosen as biocatalyst for a second step of regioselectiviy study with propylene glycol which bears primary and secondary alcohol groups. It was shown, by using several solvents, that polarity could influence the product profile in situations in which multiple products of various polarities can be formed. Furthermore, the major role of silica gel in reaction mixture was established.

Intramolecular Wittig reactions applied to the synthesis of medium sized α,β-unsaturated lactones and dilactones

A systematic study of the intramolecular Wittig reactions of ω-aldehydophosphoranes 5 has been performed and indicates that the amounts of monounsaturated lactones 6 and dilactones 7 is dependent on chain length.

A short and convergent synthesis of unsaturated macrodilactones

A simple and versatile approach to macrodiolides 1, using two consecutive Wittig reactions, is described.