Synthesis of naringin 6"-ricinoleate using immobilized lipase
Abstract Background Naringin is an important flavanone with several biological activities, including antioxidant action. However, this compound shows low solubility in lipophilic preparations, such as is used in the cosmetic and food industries. One way to solve this problem is to add fatty acids to...
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Springer Science and Business Media LLC
2012
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crspringernat:10.1186/1752-153x-6-41 2023-05-15T14:06:23+02:00 Synthesis of naringin 6"-ricinoleate using immobilized lipase Almeida, Verônica M Branco, Carla RC Assis, Sandra A Vieira, Ivo JC Braz-Filho, Raimundo Branco, Alexsandro 2012 http://dx.doi.org/10.1186/1752-153x-6-41 https://link.springer.com/content/pdf/10.1186/1752-153X-6-41.pdf https://link.springer.com/article/10.1186/1752-153X-6-41/fulltext.html en eng Springer Science and Business Media LLC https://creativecommons.org/licenses/by/2.0 https://creativecommons.org/licenses/by/2.0 CC-BY Chemistry Central Journal volume 6, issue 1 ISSN 1752-153X General Chemistry journal-article 2012 crspringernat https://doi.org/10.1186/1752-153x-6-41 2022-01-04T09:58:28Z Abstract Background Naringin is an important flavanone with several biological activities, including antioxidant action. However, this compound shows low solubility in lipophilic preparations, such as is used in the cosmetic and food industries. One way to solve this problem is to add fatty acids to the flavonoid sugar unit using immobilized lipase. However, there is limited research regarding hydroxylation of unsaturated fatty acids as an answer to the low solubility challenge. In this work, we describe the reaction of naringin with castor oil containing ricinoleic acid, castor oil's major fatty acid component, using immobilized lipase from Candida antarctica . Analysis of the 1 H and 13 C NMR (1D and 2D) spectra and literature comparison were used to characterise the obtained acyl derivative. Results After allowing the reaction to continue for 120 hours (in acetone media, 50°C), the major product obtained was naringin 6″-ricinoleate. In this reaction, either castor oil or pure ricinoleic acid was used as the acylating agent, providing a 33% or 24% yield, respectively. The chemical structure of naringin 6″-ricinoleate was determined using NMR analysis, including bidimensional (2D) experiments. Conclusion Using immobilized lipase from C. antarctica , the best conversion reaction was observed using castor oil containing ricinoleic acid as the acylating agent rather than an isolated fatty acid. Graphical abstract "Equation missing" Article in Journal/Newspaper Antarc* Antarctica Springer Nature (via Crossref) Chemistry Central Journal 6 1 |
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Springer Nature (via Crossref) |
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English |
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General Chemistry |
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General Chemistry Almeida, Verônica M Branco, Carla RC Assis, Sandra A Vieira, Ivo JC Braz-Filho, Raimundo Branco, Alexsandro Synthesis of naringin 6"-ricinoleate using immobilized lipase |
topic_facet |
General Chemistry |
description |
Abstract Background Naringin is an important flavanone with several biological activities, including antioxidant action. However, this compound shows low solubility in lipophilic preparations, such as is used in the cosmetic and food industries. One way to solve this problem is to add fatty acids to the flavonoid sugar unit using immobilized lipase. However, there is limited research regarding hydroxylation of unsaturated fatty acids as an answer to the low solubility challenge. In this work, we describe the reaction of naringin with castor oil containing ricinoleic acid, castor oil's major fatty acid component, using immobilized lipase from Candida antarctica . Analysis of the 1 H and 13 C NMR (1D and 2D) spectra and literature comparison were used to characterise the obtained acyl derivative. Results After allowing the reaction to continue for 120 hours (in acetone media, 50°C), the major product obtained was naringin 6″-ricinoleate. In this reaction, either castor oil or pure ricinoleic acid was used as the acylating agent, providing a 33% or 24% yield, respectively. The chemical structure of naringin 6″-ricinoleate was determined using NMR analysis, including bidimensional (2D) experiments. Conclusion Using immobilized lipase from C. antarctica , the best conversion reaction was observed using castor oil containing ricinoleic acid as the acylating agent rather than an isolated fatty acid. Graphical abstract "Equation missing" |
format |
Article in Journal/Newspaper |
author |
Almeida, Verônica M Branco, Carla RC Assis, Sandra A Vieira, Ivo JC Braz-Filho, Raimundo Branco, Alexsandro |
author_facet |
Almeida, Verônica M Branco, Carla RC Assis, Sandra A Vieira, Ivo JC Braz-Filho, Raimundo Branco, Alexsandro |
author_sort |
Almeida, Verônica M |
title |
Synthesis of naringin 6"-ricinoleate using immobilized lipase |
title_short |
Synthesis of naringin 6"-ricinoleate using immobilized lipase |
title_full |
Synthesis of naringin 6"-ricinoleate using immobilized lipase |
title_fullStr |
Synthesis of naringin 6"-ricinoleate using immobilized lipase |
title_full_unstemmed |
Synthesis of naringin 6"-ricinoleate using immobilized lipase |
title_sort |
synthesis of naringin 6"-ricinoleate using immobilized lipase |
publisher |
Springer Science and Business Media LLC |
publishDate |
2012 |
url |
http://dx.doi.org/10.1186/1752-153x-6-41 https://link.springer.com/content/pdf/10.1186/1752-153X-6-41.pdf https://link.springer.com/article/10.1186/1752-153X-6-41/fulltext.html |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Chemistry Central Journal volume 6, issue 1 ISSN 1752-153X |
op_rights |
https://creativecommons.org/licenses/by/2.0 https://creativecommons.org/licenses/by/2.0 |
op_rightsnorm |
CC-BY |
op_doi |
https://doi.org/10.1186/1752-153x-6-41 |
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Chemistry Central Journal |
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6 |
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1 |
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1766278089109667840 |