Enzymatic synthesis of unsaturated fatty acid glucoside esters for dermo-cosmetic applications.

Abstract:

: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.

journal_name

Biotechnol Bioeng

authors

Bousquet MP,Willemot RM,Monsan P,Boures E

doi

10.1002/(sici)1097-0290(19990620)63:6<730::aid-bit

subject

Has Abstract

pub_date

1999-06-20 00:00:00

pages

730-6

issue

6

eissn

0006-3592

issn

1097-0290

pii

10.1002/(SICI)1097-0290(19990620)63:6<730::AID-BIT

journal_volume

63

pub_type

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