Ionic Liquid‐Assisted Solubilization for Improved Enzymatic Esterification of Phenolic Acids
Abstract Lipophilic derivatives of phenolic acids could greatly extend their applications in the lipophilic bio‐environment and food processing, therefore, developing an efficient lipophilization reaction system constitutes an interesting topic of biocatalysis. Low solubility of phenolic acids in mo...
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crwiley:10.1007/s11746-011-1989-3 2024-06-23T07:48:04+00:00 Ionic Liquid‐Assisted Solubilization for Improved Enzymatic Esterification of Phenolic Acids Yang, Zhiyong Guo, Zheng Xu, Xuebing Aarhus Universitet 2012 http://dx.doi.org/10.1007/s11746-011-1989-3 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-011-1989-3 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-011-1989-3 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Journal of the American Oil Chemists' Society volume 89, issue 6, page 1049-1055 ISSN 0003-021X 1558-9331 journal-article 2012 crwiley https://doi.org/10.1007/s11746-011-1989-3 2024-06-13T04:25:41Z Abstract Lipophilic derivatives of phenolic acids could greatly extend their applications in the lipophilic bio‐environment and food processing, therefore, developing an efficient lipophilization reaction system constitutes an interesting topic of biocatalysis. Low solubility of phenolic acids in most enzyme‐benign solvents represents the main reason for the inefficiency of enzymatic production of lipophilic phenolic derivatives. This work reports a novel approach to improve Candida antartica lipase B (Novozym 435) catalyzed lipophilization of phenolic acids by means of ionic liquids (IL), trioctylmethylammonium trifluoroacetate ( t OMA.TFA) assisted solubilization of the substrate. In this approach, the IL plays two major roles, namely, to dissolve phenolic acids at high concentration so as to create a homogeneous system with another substrate—1‐octanol, and to be benign to the enzyme to keep the biocatalyst active; which is proved itself to be a correct strategy as improved conversion and volumetric productivity are obtained. The results showed that dosage of IL (denoted as the volume ratio of 1‐octanol/ t OMA.TFA), concentration of dihydrocaffeic acid (DHCA) and temperature are the key parameters governing the reaction efficiency. A maximum conversion of DHCA was achieved at the ratio of 1‐octanol/ t OMA.TFA 12:1 (v/v) (1‐octanol/DHCA, 38:1 (mol/mol)). A temperature of 70 °C was correct to obtain optimal conversion of DHCA. Even though the conversion of DHCA was higher at lower concentrations of DHCA, the overall volumetric productivity (reaction rate) was much higher when a high concentration of DHCA (1.6 M) was applied, due to IL‐assisted solubilization of DHCA. Remarkable enhancement of the conversions of ferulic and caffeic acids were achieved, when the same reaction approach ( t OMA.TFA assisted solubilization) was applied to these two phenolic acids, indicating the general applicability of this novel approach. Article in Journal/Newspaper antartic* Wiley Online Library Journal of the American Oil Chemists' Society 89 6 1049 1055 |
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English |
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Abstract Lipophilic derivatives of phenolic acids could greatly extend their applications in the lipophilic bio‐environment and food processing, therefore, developing an efficient lipophilization reaction system constitutes an interesting topic of biocatalysis. Low solubility of phenolic acids in most enzyme‐benign solvents represents the main reason for the inefficiency of enzymatic production of lipophilic phenolic derivatives. This work reports a novel approach to improve Candida antartica lipase B (Novozym 435) catalyzed lipophilization of phenolic acids by means of ionic liquids (IL), trioctylmethylammonium trifluoroacetate ( t OMA.TFA) assisted solubilization of the substrate. In this approach, the IL plays two major roles, namely, to dissolve phenolic acids at high concentration so as to create a homogeneous system with another substrate—1‐octanol, and to be benign to the enzyme to keep the biocatalyst active; which is proved itself to be a correct strategy as improved conversion and volumetric productivity are obtained. The results showed that dosage of IL (denoted as the volume ratio of 1‐octanol/ t OMA.TFA), concentration of dihydrocaffeic acid (DHCA) and temperature are the key parameters governing the reaction efficiency. A maximum conversion of DHCA was achieved at the ratio of 1‐octanol/ t OMA.TFA 12:1 (v/v) (1‐octanol/DHCA, 38:1 (mol/mol)). A temperature of 70 °C was correct to obtain optimal conversion of DHCA. Even though the conversion of DHCA was higher at lower concentrations of DHCA, the overall volumetric productivity (reaction rate) was much higher when a high concentration of DHCA (1.6 M) was applied, due to IL‐assisted solubilization of DHCA. Remarkable enhancement of the conversions of ferulic and caffeic acids were achieved, when the same reaction approach ( t OMA.TFA assisted solubilization) was applied to these two phenolic acids, indicating the general applicability of this novel approach. |
author2 |
Aarhus Universitet |
format |
Article in Journal/Newspaper |
author |
Yang, Zhiyong Guo, Zheng Xu, Xuebing |
spellingShingle |
Yang, Zhiyong Guo, Zheng Xu, Xuebing Ionic Liquid‐Assisted Solubilization for Improved Enzymatic Esterification of Phenolic Acids |
author_facet |
Yang, Zhiyong Guo, Zheng Xu, Xuebing |
author_sort |
Yang, Zhiyong |
title |
Ionic Liquid‐Assisted Solubilization for Improved Enzymatic Esterification of Phenolic Acids |
title_short |
Ionic Liquid‐Assisted Solubilization for Improved Enzymatic Esterification of Phenolic Acids |
title_full |
Ionic Liquid‐Assisted Solubilization for Improved Enzymatic Esterification of Phenolic Acids |
title_fullStr |
Ionic Liquid‐Assisted Solubilization for Improved Enzymatic Esterification of Phenolic Acids |
title_full_unstemmed |
Ionic Liquid‐Assisted Solubilization for Improved Enzymatic Esterification of Phenolic Acids |
title_sort |
ionic liquid‐assisted solubilization for improved enzymatic esterification of phenolic acids |
publisher |
Wiley |
publishDate |
2012 |
url |
http://dx.doi.org/10.1007/s11746-011-1989-3 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-011-1989-3 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-011-1989-3 |
genre |
antartic* |
genre_facet |
antartic* |
op_source |
Journal of the American Oil Chemists' Society volume 89, issue 6, page 1049-1055 ISSN 0003-021X 1558-9331 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1007/s11746-011-1989-3 |
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Journal of the American Oil Chemists' Society |
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89 |
container_issue |
6 |
container_start_page |
1049 |
op_container_end_page |
1055 |
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1802638479434186752 |