Synthesis and properties of ascorbyl esters catalyzed by lipozyme TL im using triglycerides as acyl donors
[EN] Esters of l-ascorbic acid with long-chain fatty acids (E-304) are employed as antioxidants in foods rich in lipids. Although their enzymatic synthesis offers some advantages compared with the current chemical processes, most of the reported methods employ the immobilized lipase from Candida ant...
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Online Access: | http://hdl.handle.net/10261/227278 https://doi.org/10.1007/s11746-010-1643-5 https://doi.org/10.13039/501100003339 https://doi.org/10.13039/100012818 |
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ftcsic:oai:digital.csic.es:10261/227278 2024-02-11T09:56:50+01:00 Synthesis and properties of ascorbyl esters catalyzed by lipozyme TL im using triglycerides as acyl donors Reyes-Duarte, Dolores López-Cortés, Nieves Torres, Pamela Comelles, Francesc Parra, J.L. Peña, S. Ugidos, A.V Ballesteros Olmo, Antonio Plou Gasca, Francisco José Comunidad de Madrid Consejo Superior de Investigaciones Científicas (España) 2011 http://hdl.handle.net/10261/227278 https://doi.org/10.1007/s11746-010-1643-5 https://doi.org/10.13039/501100003339 https://doi.org/10.13039/100012818 unknown Springer Postprint http://dx.doi.org/10.1007/s11746-010-1643-5 Sí doi:10.1007/s11746-010-1643-5 issn: 0003-021X e-issn: 1558-9331 JAOCS, Journal of the American Oil Chemists' Society 88: 57- 64 (2011) http://hdl.handle.net/10261/227278 http://dx.doi.org/10.13039/501100003339 http://dx.doi.org/10.13039/100012818 open Vitamin C Ascorbyl esters L-Ascorbyl oleate Lipase Thermomyces lanuginosus Enzymatic transesterification Alkyl esters Triglycerides Surface tension CMC Antioxidant activity artículo http://purl.org/coar/resource_type/c_6501 2011 ftcsic https://doi.org/10.1007/s11746-010-1643-510.13039/50110000333910.13039/100012818 2024-01-16T11:01:37Z [EN] Esters of l-ascorbic acid with long-chain fatty acids (E-304) are employed as antioxidants in foods rich in lipids. Although their enzymatic synthesis offers some advantages compared with the current chemical processes, most of the reported methods employ the immobilized lipase from Candida antarctica as biocatalyst and free fatty acids or activated esters as acyl donors. In order to diminish the cost of the process, we have investigated the synthesis of ascorbyl oleate and ascorbyl palmitate esters with the immobilized Thermomyces lanuginosus lipase Lipozyme TL IM-which is significantly less expensive than Novozym 435-and triglycerides as source of fatty acids. Lipozyme TL IM gave rise to a lower yield of 6-O-ascorbyl oleate than Novozym 435 when using triolein (64 vs. 84%) and olive oil (27 vs. 33%) as acyl donors. Both 6-O-ascorbyl oleate and 6-O-ascorbyl palmitate displayed excellent surfactant and antioxidant properties. The Trolox Equivalent Antioxidant Capability values for the oleate and palmitate were 71 and 84%, respectively, of those obtained with l-ascorbic acid; however, both derivatives were able to stabilize soybean oil towards peroxide formation. © 2010 AOCS. Comunidad de Madrid for a research contract to P. Torres and to CONACYT for grant 020256 to D. Reyes. This research was supported by the Spanish CSIC (Project 200680F0132) and by the Latin-American Science & Technology Development Programme (CYTED Project 108RT0346). Article in Journal/Newspaper Antarc* Antarctica Digital.CSIC (Spanish National Research Council) Journal of the American Oil Chemists' Society 88 1 57 64 |
institution |
Open Polar |
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Digital.CSIC (Spanish National Research Council) |
op_collection_id |
ftcsic |
language |
unknown |
topic |
Vitamin C Ascorbyl esters L-Ascorbyl oleate Lipase Thermomyces lanuginosus Enzymatic transesterification Alkyl esters Triglycerides Surface tension CMC Antioxidant activity |
spellingShingle |
Vitamin C Ascorbyl esters L-Ascorbyl oleate Lipase Thermomyces lanuginosus Enzymatic transesterification Alkyl esters Triglycerides Surface tension CMC Antioxidant activity Reyes-Duarte, Dolores López-Cortés, Nieves Torres, Pamela Comelles, Francesc Parra, J.L. Peña, S. Ugidos, A.V Ballesteros Olmo, Antonio Plou Gasca, Francisco José Synthesis and properties of ascorbyl esters catalyzed by lipozyme TL im using triglycerides as acyl donors |
topic_facet |
Vitamin C Ascorbyl esters L-Ascorbyl oleate Lipase Thermomyces lanuginosus Enzymatic transesterification Alkyl esters Triglycerides Surface tension CMC Antioxidant activity |
description |
[EN] Esters of l-ascorbic acid with long-chain fatty acids (E-304) are employed as antioxidants in foods rich in lipids. Although their enzymatic synthesis offers some advantages compared with the current chemical processes, most of the reported methods employ the immobilized lipase from Candida antarctica as biocatalyst and free fatty acids or activated esters as acyl donors. In order to diminish the cost of the process, we have investigated the synthesis of ascorbyl oleate and ascorbyl palmitate esters with the immobilized Thermomyces lanuginosus lipase Lipozyme TL IM-which is significantly less expensive than Novozym 435-and triglycerides as source of fatty acids. Lipozyme TL IM gave rise to a lower yield of 6-O-ascorbyl oleate than Novozym 435 when using triolein (64 vs. 84%) and olive oil (27 vs. 33%) as acyl donors. Both 6-O-ascorbyl oleate and 6-O-ascorbyl palmitate displayed excellent surfactant and antioxidant properties. The Trolox Equivalent Antioxidant Capability values for the oleate and palmitate were 71 and 84%, respectively, of those obtained with l-ascorbic acid; however, both derivatives were able to stabilize soybean oil towards peroxide formation. © 2010 AOCS. Comunidad de Madrid for a research contract to P. Torres and to CONACYT for grant 020256 to D. Reyes. This research was supported by the Spanish CSIC (Project 200680F0132) and by the Latin-American Science & Technology Development Programme (CYTED Project 108RT0346). |
author2 |
Comunidad de Madrid Consejo Superior de Investigaciones Científicas (España) |
format |
Article in Journal/Newspaper |
author |
Reyes-Duarte, Dolores López-Cortés, Nieves Torres, Pamela Comelles, Francesc Parra, J.L. Peña, S. Ugidos, A.V Ballesteros Olmo, Antonio Plou Gasca, Francisco José |
author_facet |
Reyes-Duarte, Dolores López-Cortés, Nieves Torres, Pamela Comelles, Francesc Parra, J.L. Peña, S. Ugidos, A.V Ballesteros Olmo, Antonio Plou Gasca, Francisco José |
author_sort |
Reyes-Duarte, Dolores |
title |
Synthesis and properties of ascorbyl esters catalyzed by lipozyme TL im using triglycerides as acyl donors |
title_short |
Synthesis and properties of ascorbyl esters catalyzed by lipozyme TL im using triglycerides as acyl donors |
title_full |
Synthesis and properties of ascorbyl esters catalyzed by lipozyme TL im using triglycerides as acyl donors |
title_fullStr |
Synthesis and properties of ascorbyl esters catalyzed by lipozyme TL im using triglycerides as acyl donors |
title_full_unstemmed |
Synthesis and properties of ascorbyl esters catalyzed by lipozyme TL im using triglycerides as acyl donors |
title_sort |
synthesis and properties of ascorbyl esters catalyzed by lipozyme tl im using triglycerides as acyl donors |
publisher |
Springer |
publishDate |
2011 |
url |
http://hdl.handle.net/10261/227278 https://doi.org/10.1007/s11746-010-1643-5 https://doi.org/10.13039/501100003339 https://doi.org/10.13039/100012818 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
Postprint http://dx.doi.org/10.1007/s11746-010-1643-5 Sí doi:10.1007/s11746-010-1643-5 issn: 0003-021X e-issn: 1558-9331 JAOCS, Journal of the American Oil Chemists' Society 88: 57- 64 (2011) http://hdl.handle.net/10261/227278 http://dx.doi.org/10.13039/501100003339 http://dx.doi.org/10.13039/100012818 |
op_rights |
open |
op_doi |
https://doi.org/10.1007/s11746-010-1643-510.13039/50110000333910.13039/100012818 |
container_title |
Journal of the American Oil Chemists' Society |
container_volume |
88 |
container_issue |
1 |
container_start_page |
57 |
op_container_end_page |
64 |
_version_ |
1790606205555572736 |