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Synthesis with Immobilized Lipases and Downstream Processing of Ascorbyl Palmitate

Ascorbyl palmitate is a fatty acid ester endowed with antioxidant properties, used as a food additive and cosmetic ingredient, which is presently produced by chemical synthesis. Ascorbyl palmitate was synthesized from ascorbic acid and palmitic acid with a Pseudomonas stutzeri lipase immobilized on...

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Autores principales: Tufiño, Carolina, Bernal, Claudia, Ottone, Carminna, Romero, Oscar, Illanes, Andrés, Wilson, Lorena
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6767233/
https://www.ncbi.nlm.nih.gov/pubmed/31491845
http://dx.doi.org/10.3390/molecules24183227
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author Tufiño, Carolina
Bernal, Claudia
Ottone, Carminna
Romero, Oscar
Illanes, Andrés
Wilson, Lorena
author_facet Tufiño, Carolina
Bernal, Claudia
Ottone, Carminna
Romero, Oscar
Illanes, Andrés
Wilson, Lorena
author_sort Tufiño, Carolina
collection PubMed
description Ascorbyl palmitate is a fatty acid ester endowed with antioxidant properties, used as a food additive and cosmetic ingredient, which is presently produced by chemical synthesis. Ascorbyl palmitate was synthesized from ascorbic acid and palmitic acid with a Pseudomonas stutzeri lipase immobilized on octyl silica, and also with the commercial immobilized lipase Novozym 435. The latter was selected for optimizing the reaction conditions because of its high reactivity and stability in the solvent 2-methyl-2-butanol used as reaction medium. The reaction of the synthesis was studied considering temperature and molar ratio of substrates as variables and synthesis yield as response parameter. The highest yield in the synthesis of ascorbyl palmitate was 81%, obtained at 55 °C and an ascorbic acid to palmitic acid molar ratio of 1:8, both variables having a strong effect on yield. The synthesized ascorbyl palmitate was purified to 94.4%, with a purification yield of 84.2%. The use of generally recognized as safe (GRAS) certified solvents with a polarity suitable for the solubilization of the compounds made the process a viable alternative for the synthesis and downstream processing of ascorbyl palmitate.
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spelling pubmed-67672332019-10-02 Synthesis with Immobilized Lipases and Downstream Processing of Ascorbyl Palmitate Tufiño, Carolina Bernal, Claudia Ottone, Carminna Romero, Oscar Illanes, Andrés Wilson, Lorena Molecules Article Ascorbyl palmitate is a fatty acid ester endowed with antioxidant properties, used as a food additive and cosmetic ingredient, which is presently produced by chemical synthesis. Ascorbyl palmitate was synthesized from ascorbic acid and palmitic acid with a Pseudomonas stutzeri lipase immobilized on octyl silica, and also with the commercial immobilized lipase Novozym 435. The latter was selected for optimizing the reaction conditions because of its high reactivity and stability in the solvent 2-methyl-2-butanol used as reaction medium. The reaction of the synthesis was studied considering temperature and molar ratio of substrates as variables and synthesis yield as response parameter. The highest yield in the synthesis of ascorbyl palmitate was 81%, obtained at 55 °C and an ascorbic acid to palmitic acid molar ratio of 1:8, both variables having a strong effect on yield. The synthesized ascorbyl palmitate was purified to 94.4%, with a purification yield of 84.2%. The use of generally recognized as safe (GRAS) certified solvents with a polarity suitable for the solubilization of the compounds made the process a viable alternative for the synthesis and downstream processing of ascorbyl palmitate. MDPI 2019-09-05 /pmc/articles/PMC6767233/ /pubmed/31491845 http://dx.doi.org/10.3390/molecules24183227 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tufiño, Carolina
Bernal, Claudia
Ottone, Carminna
Romero, Oscar
Illanes, Andrés
Wilson, Lorena
Synthesis with Immobilized Lipases and Downstream Processing of Ascorbyl Palmitate
title Synthesis with Immobilized Lipases and Downstream Processing of Ascorbyl Palmitate
title_full Synthesis with Immobilized Lipases and Downstream Processing of Ascorbyl Palmitate
title_fullStr Synthesis with Immobilized Lipases and Downstream Processing of Ascorbyl Palmitate
title_full_unstemmed Synthesis with Immobilized Lipases and Downstream Processing of Ascorbyl Palmitate
title_short Synthesis with Immobilized Lipases and Downstream Processing of Ascorbyl Palmitate
title_sort synthesis with immobilized lipases and downstream processing of ascorbyl palmitate
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6767233/
https://www.ncbi.nlm.nih.gov/pubmed/31491845
http://dx.doi.org/10.3390/molecules24183227
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