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Highly Efficient Synthesis of an Emerging Lipophilic Antioxidant: 2-Ethylhexyl Ferulate

Ferulic acid in ester form has shown a stronger ability in ameliorating certain pathological conditions and inhibiting lipid oxidation. In present study, a solvent-free and reduced pressure evaporation system was developed for lipase-catalyzed synthesis of 2-ethylhexyl ferulate (2-EF) from ferulic a...

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Autores principales: Huang, Kuo-Chuan, Li, Ying, Kuo, Chia-Hung, Twu, Yawo-Kuo, Shieh, Chwen-Jen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274311/
https://www.ncbi.nlm.nih.gov/pubmed/27077838
http://dx.doi.org/10.3390/molecules21040478
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author Huang, Kuo-Chuan
Li, Ying
Kuo, Chia-Hung
Twu, Yawo-Kuo
Shieh, Chwen-Jen
author_facet Huang, Kuo-Chuan
Li, Ying
Kuo, Chia-Hung
Twu, Yawo-Kuo
Shieh, Chwen-Jen
author_sort Huang, Kuo-Chuan
collection PubMed
description Ferulic acid in ester form has shown a stronger ability in ameliorating certain pathological conditions and inhibiting lipid oxidation. In present study, a solvent-free and reduced pressure evaporation system was developed for lipase-catalyzed synthesis of 2-ethylhexyl ferulate (2-EF) from ferulic acid and 2-ethylhexanol. A Box-Behnken design with response surface methodology (RSM) and artificial neural network (ANN) was selected to model and optimize the process. Based on the yields of 2-EF, reaction temperature was shown to be the most important process factor on the molar conversion among all variables. The residual values and the coefficient of determination (R(2)) calculated from the design data indicated that ANN was better than RSM in data fitting. Overall, the present lipase-catalyzed approach for 2-EF synthesis at low reaction temperature in a reduced pressure evaporation system shows high 2-EF production efficiency. Notably, this approach can reduce the enzyme denaturation and ferulic acid oxidation that usually occur during long-term biosynthetic operations at high temperature.
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spelling pubmed-62743112018-12-28 Highly Efficient Synthesis of an Emerging Lipophilic Antioxidant: 2-Ethylhexyl Ferulate Huang, Kuo-Chuan Li, Ying Kuo, Chia-Hung Twu, Yawo-Kuo Shieh, Chwen-Jen Molecules Article Ferulic acid in ester form has shown a stronger ability in ameliorating certain pathological conditions and inhibiting lipid oxidation. In present study, a solvent-free and reduced pressure evaporation system was developed for lipase-catalyzed synthesis of 2-ethylhexyl ferulate (2-EF) from ferulic acid and 2-ethylhexanol. A Box-Behnken design with response surface methodology (RSM) and artificial neural network (ANN) was selected to model and optimize the process. Based on the yields of 2-EF, reaction temperature was shown to be the most important process factor on the molar conversion among all variables. The residual values and the coefficient of determination (R(2)) calculated from the design data indicated that ANN was better than RSM in data fitting. Overall, the present lipase-catalyzed approach for 2-EF synthesis at low reaction temperature in a reduced pressure evaporation system shows high 2-EF production efficiency. Notably, this approach can reduce the enzyme denaturation and ferulic acid oxidation that usually occur during long-term biosynthetic operations at high temperature. MDPI 2016-04-12 /pmc/articles/PMC6274311/ /pubmed/27077838 http://dx.doi.org/10.3390/molecules21040478 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Huang, Kuo-Chuan
Li, Ying
Kuo, Chia-Hung
Twu, Yawo-Kuo
Shieh, Chwen-Jen
Highly Efficient Synthesis of an Emerging Lipophilic Antioxidant: 2-Ethylhexyl Ferulate
title Highly Efficient Synthesis of an Emerging Lipophilic Antioxidant: 2-Ethylhexyl Ferulate
title_full Highly Efficient Synthesis of an Emerging Lipophilic Antioxidant: 2-Ethylhexyl Ferulate
title_fullStr Highly Efficient Synthesis of an Emerging Lipophilic Antioxidant: 2-Ethylhexyl Ferulate
title_full_unstemmed Highly Efficient Synthesis of an Emerging Lipophilic Antioxidant: 2-Ethylhexyl Ferulate
title_short Highly Efficient Synthesis of an Emerging Lipophilic Antioxidant: 2-Ethylhexyl Ferulate
title_sort highly efficient synthesis of an emerging lipophilic antioxidant: 2-ethylhexyl ferulate
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274311/
https://www.ncbi.nlm.nih.gov/pubmed/27077838
http://dx.doi.org/10.3390/molecules21040478
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