Enzymatic synthesis of unsaturated fatty acid glucoside esters for dermo-cosmetic applications.
Unsaturated fatty acid alpha-butylglucoside esters were prepared by enzymatic esterification of alpha-butylglucoside in nonaqueous media. Conditions were firstly optimized using oleic acid as acyl group. Synthesis was possible in several solvents but the presence of water co-product in the medium limited the reaction to a thermodynamic equilibrium corresponding to a maximal conversion yield of 62%. In pure molten substrates, the removal of water under reduced pressure enabled yields superior to 95% to be obtained. Product profiles depended on enzyme origin : whatever the support, immobilized lipase B from Candida antarctica proved to be far more regioselective for the primary hydroxyl group of glucose than immobilized lipase from Rhizomucor miehei. Results obtained could be easily transposed to the acylation of alpha-butylglucoside with a commercial mixture of unsaturated fatty acids containing more than 60% of linoleic acid. The biocatalyst could be recycled more than ten times without any significant activity loss.
Centre de Bioingénierie Gilbert Durand, Département de Génie Biochimique et Alimentaire, UMR CNRS 5504, LA INRA, INSA, Complexe Scientifique de Rangueil, F-31077 Toulouse Cédex 4, France.
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Bousquet
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Willemot
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Monsan
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Boures
D000215:Acylation; D000440:Butanols / Q000138:chemical synthesis; D003358:Cosmetics / Q000138:chemical synthesis* / Q000737:chemistry*; D004795:Enzyme Stability; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D005960:Glucosides / Q000138:chemical synthesis*; D019787:Linoleic Acid / Q000737:chemistry; D008041:Linoleic Acids / Q000138:chemical synthesis*; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry / Q000379:methods; D019301:Oleic Acid / Q000737:chemistry; D000439:Pentanols; D012997:Solvents / Q000737:chemistry; D017962:alpha-Linolenic Acid / Q000737:chemistry
D000440:Butanols; D003358:Cosmetics; D004952:Esters; D005231:Fatty Acids, Unsaturated; D005960:Glucosides; D008041:Linoleic Acids; D000439:Pentanols; D012997:Solvents; C120359:butylglucoside linoleate; D017962:alpha-Linolenic Acid; D019301:Oleic Acid; C032765:tert-amyl alcohol; D019787:Linoleic Acid; D008049:Lipase