Abstract
A novel approach is reported for the synthesis of dihydrocaffoylated glycerols that consists of two steps: enzymatic synthesis of octyl dihydrocaffeate (as a synthetic intermediate) from octanol and dihydrocaffeic acid, and enzymatic interesterification of triacylglycerols with octyl dihydrocaffeate. Due to the good compatibility of the intermediate with triacylglycerols, an improved volumetric productivity [147 mol h−1(kg Novozym 435)−1] and high enzyme specific activity [up to 9.6 μmol−1 min−1(g Novozym 435)−1] have been obtained.
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Buisman GJH, van Helteren CTW, Kramer GFH, Veldsink JW, Derksen JTP, Cuperus FP (1998) Enzymatic esterifications of functionalized phenols for the synthesis of lipophilic antioxidants. Biotechnol Lett 20:131–136
Compton DL, Laszlo JA, Berhow MA (2000) Lipase-catalyzed synthesis of ferulate esters. J Am Oil Chem Soc 77:513–519
Compton DL, Laszlo JA, Berhow MA (2006) Identification and quantification of feruloylated mono-, di-, and triacylglycerols from vegetable oils. J Am Oil Chem Soc 83:753–758
Figueroa-Espinoza MC, Villeneuve P (2005) Phenolic acids enzymatic lipophilization. J Agric Food Chem 53:2779–2787
Guyot B, Bosquette B, Pina M, Graille J (1997) Esterification of phenolic acids from green coffee with an immobilized lipase from Candida antarctica in solvent-free medium. Biotechnol Lett 19:529–532
Laszlo JA, Compton DL (2006) Enzymatic glycerolysis and transesterification of vegetable oil for enhanced production of feruloylated glycerols. J Am Oil Chem Soc 83:765–770
Lue BM, Karboune S, Yeboah FK, Kermasha S (2005) Lipase-catalyzed esterification of cinnamic acid and oleyl alcohol in organic solvent media. J Chem Technol Biotechnol 80:462–468
Sabally K, Karboune S, Yebaoh FK, Kermasha S (2005) Enzymatic esterification of dihydrocaffeic acid with linoleyl alcohol in organic solvent media. Biocatal Biotransform 23:37–44
Sabally K, Karboune S, St-Louis R, Kermasha S (2006) Lipase-catalyzed transesterification of trilinolein or trilinolenin with selected phenolic acids. J Am Oil Chem Soc 83:101–107
Sabally K, Karboune S, St-Louis R, Kermasha S (2007) Lipase-catalyzed synthesis of phenolic lipids from fish liver oil and dihydrocaffeic acid. Biocatal Biotransform 25:211–218
Safari M, Karboune S, St-Louis R, Kermasha S (2006) Enzymatic synthesis of structured phenolic lipids by incorporation of selected phenolic acids into triolein. Biocatal Biotransform 24:272–279
Stamatis H, Sereti V, Kolisis FN (1999) Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants. J Am Oil Chem Soc 76:1505–1510
Stamatis H, Sereti V, Kolisis FN (2001) Enzymatic synthesis of hydrophilic and hydrophobic derivatives of natural phenolic acids in organic media. J Mol Catal B: Enzym 11:323–328
Sun S, Yang G, Bi Y, Xiao F (2009) Chemoenzymatic synthesis of feruloylated monoacyl- and diacyl-glycerols in ionic liquids. Biotechnol Lett 31:1885–1889
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Financial support from the Strategic Food and Health Program (FøSu) and the Grant from the Graduate School of Science, Aarhus University are gratefully acknowledged.
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Yang, Z., Feddern, V., Glasius, M. et al. Improved enzymatic production of phenolated acylglycerols through alkyl phenolate intermediates. Biotechnol Lett 33, 673–679 (2011). https://doi.org/10.1007/s10529-010-0486-3
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DOI: https://doi.org/10.1007/s10529-010-0486-3