Synthesis of octyl dihydrocaffeate and its transesterification with tricaprylin catalyzed by Candida antarctica lipase

Industrial and Engineering Chemistry Research

Volumn 50, Issue 12, 2011, Pages 7183-7190

  Feddern, Vivian ^a   Yang, Zhiyong ^a   Xu, Xuebing ^a   Badiale Furlong, Eliana ^a   De Souza Soares, Leonor Almeida ^a  

^a EMBRAPA CERRADOS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CANDIDA ANTARCTICA; CENTRAL COMPOSITE ROTATABLE DESIGN; ESTERIFICATION REACTIONS; HIGHER TEMPERATURES; NOVOZYM435; PHENOLIC COMPOUNDS; PHENOLIC ESTERS; REAGENT CONSUMPTION; TRANSESTERIFICATION REACTION;

ESTERIFICATION; ESTERS; PHENOLS; SYNTHESIS (CHEMICAL);

TRANSESTERIFICATION;

EID: 79958810668     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie200034y     Document Type: Article

References (27)

1. Stevenson, D. E.; Parkar, S. G.; Zhang, J.; Stanley, R. A.; Jensen, D. J.; Cooney, J. M. Combinatorial enzymic synthesis for functional testing of phenolic acid esters catalysed by Candida antarctica lipase B (Novozym 435) Enzyme Microb. Technol. 2007, 40, 1078
2. Gugliucci, A.; Bastos, D. H. M.; Schulze, J.; Souza, M. F. F. Caffeic and chlorogenic acids in Ilex paraguariensis extracts are the main inhibitors of AGE generation by methylglyoxal in model proteins Fitoterapia 2009, 80, 339
3. Figueroa-Espinoza, M. C.; Villeneuve, P. Phenolic acids enzymatic lipophilization J. Agric. Food Chem. 2005, 53, 2779
4. Huang, J.; Paulis, T.; May, J. M. Antioxidant effects of dihydrocaffeic acid in human EA.hy926 endothelial cells J. Nutr. Biochem. 2004, 15, 722
5. Stamatis, H.; Sereti, V.; Kolisis, F. N. Enzymatic synthesis of hydrophilic and hydrophobic derivatives of natural phenolic acids in organic media J. Mol. Catal. B: Enzym. 2001, 11, 323
6. Silva, F. A. M.; Borges, F.; Guimarães, C.; Lima, J. L. F. C.; Matos, C.; Reis, S. Phenolic acids and derivatives: studies on the relationship among structure, radical scavenging activity, and physicochemical parameters J. Agric. Food Chem. 2000, 48, 2122
7. Sabally, K.; Karboune, S.; St-Louis, R.; Kermasha, S. Lipase-catalyzed transesterification of dihydrocaffeic acid with flaxseed oil for the synthesis of phenolic lipids J. Biotechnol. 2006, 127, 167
8. Sabally, K.; Karboune, S.; St-Louis, R.; Kermasha, S. Lipase-catalyzed synthesis of phenolic lipids from fish liver oil and dihydrocaffeic acid Biocatal. Biotransform. 2007, 25, 211
9. Kahveci, D.; Guo, Z.; Özçelik, B.; Xu, X. Lipase-catalyzed glycerolysis in ionic liquids directed towards diglyceride synthesis Process Biochem. 2009, 44, 1358
10. Devi, B. L. A. P.; Zhang, H.; Damstrup, M. L.; Guo, Z.; Zhang, L.; Lue, B.-M.; Xu, X. Enzymatic synthesis of designer lipids OCL-Ol. Corps Gras Li. 2008, 15, 189
11. Otto, R. T.; Scheib, H.; Bornscheuer, U. T.; Pleiss, J.; Syldatk, C.; Schmid, R. D. Substrate specificity of lipase B from Candida antarctica in the synthesis of arylaliphatic glycolipids J. Mol. Catal. B: Enzym. 2000, 8, 201
12. Cassani, J.; Luna, H.; Navarro, A.; Castillo, E. Comparative esterification of phenylpropanoids versus hydrophenylpropanoids acids catalyzed by lipase in organic solvent media Electron. J. Biotechnol. 2007, 10, 508
13. Lee, K. T.; Akoh, C. C. Characterization of enzymatically synthesized structured lipids containing eicosapentaenoic, docosahexaenoic, and caprylic acids J. Am. Oil Chem. Soc. 1998, 75, 495
14. Yang, Z.; Feddern, V.; Glasius, M.; Guo, Z.; Xu, X. Improved enzymatic production of phenolated acylglycerols through alkyl phenolate intermediates Biotechnol. Lett. 2011, 33, 673
15. Brusamarelo, C. Z.; Rosset, E.; Césaro, A.; Treichel, H.; Oliveira, D.; Mazutti, M. A.; Di Luccio, M.; Oliveira, J. V. Kinetics of lipase-catalyzed synthesis of soybean fatty acid ethyl esters in pressurized propane J. Biotechnol. 2010, 147, 108
16. Sun, S.; Shan, L.; Liu, Y.; Jin, Q.; Song, Y.; Wang, X. Solvent-free enzymatic synthesis of feruloylated diacylglycerols and kinetic study J. Mol. Catal. B: Enzym. 2009, 57, 104
17. Oliveira, D.; Luccio, M.; Di; Faccio, C.; Rosa, C. D.; Bender, J. P.; Lipke, N.; Menoncin, S.; Amroginski, C.; Oliveira, J. V. Optimization of enzymatic production of biodiesel from castor oil in organic solvent medium Appl. Biochem. Biotechnol. 2004, 115, 771
18. Oliveira, D.; Alves, T. L. M. A kinetic study of lipase catalyzed alcoholysis of palm kernel oil Appl. Biochem. Biotechnol. 2000, 84-86, 59
19. Karboune, S.; Safari, M.; Lue, B.-M.; Yeboah, F. K.; Kermasha, S. Lipase-catalyzed biosynthesis of cinnamoylated lipids in a selected organic solvent medium J. Biotechnol. 2005, 119, 281
20. Lue, B.-M.; Karboune, S.; Yeboah, F. K.; Kermasha, S. Lipase-catalyzed esterification of cinnamic acid and oleyl alcohol in organic solvent media J. Chem. Technol. Biotechnol. 2005, 80, 462
21. Macedo, G. A.; Lozano, M. M. S.; Pastore, G. M. Enzymatic synthesis of short chain citronellyl esters by a new lipase from Rhizopus sp Electron. J. Biotechnol. 2003, 6, 72
22. Yang, T.; Rebsdorf, M.; Engelrud, U.; Xu, X. Monoacylglycerol synthesis via enzymatic glycerolysis in an efficient reaction system J. Food Lipids 2005, 12, 299
23. Hu, Y.; Guo, Z.; Lue, B.-M.; Xu, X. Enzymatic synthesis of lipophilic flavonoid derivatives in ionic liquids buffered with organic solvents J. Agric. Food Chem. 2009, 57, 3845
24. Prabhavathi Devi, B. L. A.; Guo, Z.; Xu, X. Characterization of cross-linked lipase aggregates J. Am. Oil Chem. Soc. 2009, 86, 637
25. Xin, J.-y.; Zhang, L.; Chen, L.-l.; Zheng, Y.; Wu, X.-m.; Xia, C.-g. Lipase-catalyzed synthesis of ferulyl oleins in solvent-free medium Food Chem. 2009, 112, 640
26. Sun, S.; Shan, L.; Liu, Y.; Jin, Q.; Song, Y.; Wang, X. Solvent-free enzymatic synthesis of feruloylated diacylglycerols and kinetic study J. Mol. Catal. B: Enzym. 2009, 57, 104
27. Edreva, A. The importance of non-photosynthetic pigments and cinnamic acid derivatives in photoprotection Agric. Ecosyst. Environ. 2005, 106, 135