Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification
Lipases were employed under solvent-free conditions to conjugate oligo-ricinoleic acid derivatives with 10-undecenoic acid, to incorporate a reactive terminal double bond into the resultant product. First, undecenoic acid was covalently attached to oligo-ricinoleic acid using immobilized Candida ant...
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Molecular Diversity Preservation International
2012
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ftmdpi:oai:mdpi.com:/2073-4360/4/2/1037/ 2023-08-20T04:01:42+02:00 Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification Douglas G. Hayes Vinay K. Mannam Ran Ye Haizhen Zhao Salvadora Ortega M. Claudia Montiel 2012-04-17 application/pdf https://doi.org/10.3390/polym4021037 EN eng Molecular Diversity Preservation International https://dx.doi.org/10.3390/polym4021037 https://creativecommons.org/licenses/by/3.0/ Polymers; Volume 4; Issue 2; Pages: 1037-1055 biobased polyesters; castor oil lipases oligo -ricinoleic acid polyglycerol polyricinoleate ricinoleic acid 10-undecenoic acid Text 2012 ftmdpi https://doi.org/10.3390/polym4021037 2023-07-31T20:28:43Z Lipases were employed under solvent-free conditions to conjugate oligo-ricinoleic acid derivatives with 10-undecenoic acid, to incorporate a reactive terminal double bond into the resultant product. First, undecenoic acid was covalently attached to oligo-ricinoleic acid using immobilized Candida antarctica lipase (CAL) at a 30% yield. Thirty percent conversion also occurred for CAL-catalyzed esterification between undecenoic acid and biocatalytically-prepared polyglycerol polyricinoleate (PGPR), with attachment of undecenoic acid occurring primarily at free hydroxyls of the polyglycerol moiety. The synthesis of oligo-ricinoleyl-, undecenoyl- structured triacylglycerols comprised two steps. The first step, the 1,3-selective lipase-catalyzed interesterification of castor oil with undecenoic acid, occurred successfully. The second step, the CAL-catalyzed reaction between ricinoleyl-, undecenoyl structured TAG and ricinoleic acid, yielded approximately 10% of the desired structured triacylglycerols (TAG); however, a significant portion of the ricinoleic acid underwent self-polymerization as a side-reaction. The employment of gel permeation chromatography, normal phase HPLC, NMR, and acid value measurements was effective for characterizing the reaction pathways and products that formed. Text Antarc* Antarctica MDPI Open Access Publishing Polymers 4 2 1037 1055 |
institution |
Open Polar |
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MDPI Open Access Publishing |
op_collection_id |
ftmdpi |
language |
English |
topic |
biobased polyesters; castor oil lipases oligo -ricinoleic acid polyglycerol polyricinoleate ricinoleic acid 10-undecenoic acid |
spellingShingle |
biobased polyesters; castor oil lipases oligo -ricinoleic acid polyglycerol polyricinoleate ricinoleic acid 10-undecenoic acid Douglas G. Hayes Vinay K. Mannam Ran Ye Haizhen Zhao Salvadora Ortega M. Claudia Montiel Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification |
topic_facet |
biobased polyesters; castor oil lipases oligo -ricinoleic acid polyglycerol polyricinoleate ricinoleic acid 10-undecenoic acid |
description |
Lipases were employed under solvent-free conditions to conjugate oligo-ricinoleic acid derivatives with 10-undecenoic acid, to incorporate a reactive terminal double bond into the resultant product. First, undecenoic acid was covalently attached to oligo-ricinoleic acid using immobilized Candida antarctica lipase (CAL) at a 30% yield. Thirty percent conversion also occurred for CAL-catalyzed esterification between undecenoic acid and biocatalytically-prepared polyglycerol polyricinoleate (PGPR), with attachment of undecenoic acid occurring primarily at free hydroxyls of the polyglycerol moiety. The synthesis of oligo-ricinoleyl-, undecenoyl- structured triacylglycerols comprised two steps. The first step, the 1,3-selective lipase-catalyzed interesterification of castor oil with undecenoic acid, occurred successfully. The second step, the CAL-catalyzed reaction between ricinoleyl-, undecenoyl structured TAG and ricinoleic acid, yielded approximately 10% of the desired structured triacylglycerols (TAG); however, a significant portion of the ricinoleic acid underwent self-polymerization as a side-reaction. The employment of gel permeation chromatography, normal phase HPLC, NMR, and acid value measurements was effective for characterizing the reaction pathways and products that formed. |
format |
Text |
author |
Douglas G. Hayes Vinay K. Mannam Ran Ye Haizhen Zhao Salvadora Ortega M. Claudia Montiel |
author_facet |
Douglas G. Hayes Vinay K. Mannam Ran Ye Haizhen Zhao Salvadora Ortega M. Claudia Montiel |
author_sort |
Douglas G. Hayes |
title |
Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification |
title_short |
Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification |
title_full |
Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification |
title_fullStr |
Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification |
title_full_unstemmed |
Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification |
title_sort |
modification of oligo-ricinoleic acid and its derivatives with 10-undecenoic acid via lipase-catalyzed esterification |
publisher |
Molecular Diversity Preservation International |
publishDate |
2012 |
url |
https://doi.org/10.3390/polym4021037 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Polymers; Volume 4; Issue 2; Pages: 1037-1055 |
op_relation |
https://dx.doi.org/10.3390/polym4021037 |
op_rights |
https://creativecommons.org/licenses/by/3.0/ |
op_doi |
https://doi.org/10.3390/polym4021037 |
container_title |
Polymers |
container_volume |
4 |
container_issue |
2 |
container_start_page |
1037 |
op_container_end_page |
1055 |
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