Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid
The aim of this work was the synthesis of a novel hydroxyl-fatty acid derivative of kojic acid rich in kojic acid monoricinoleate (KMR) which can be widely used in the cosmetic and food industry. The synthesis of KMR was carried out by lipase-catalysed esterification of ricinoleic and kojic acids in...
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| Format: | Article |
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Elsevier
2014
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| _version_ | 1825948641724989440 |
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| author | El-Boulifi, Noureddin Ashari, Siti Efliza Serrano, Marta Aracil, Jose Martínez, Mercedes |
| author_facet | El-Boulifi, Noureddin Ashari, Siti Efliza Serrano, Marta Aracil, Jose Martínez, Mercedes |
| author_sort | El-Boulifi, Noureddin |
| collection | UPM |
| description | The aim of this work was the synthesis of a novel hydroxyl-fatty acid derivative of kojic acid rich in kojic acid monoricinoleate (KMR) which can be widely used in the cosmetic and food industry. The synthesis of KMR was carried out by lipase-catalysed esterification of ricinoleic and kojic acids in solvent-free system. Three immobilized lipases were tested and the best KMR yields were attained with Lipozyme TL IM and Novozym 435. Since Lipozyme TL IM is the cheapest, it was selected to optimize the reaction conditions. The optimal reaction conditions were 80 °C for the temperature, 1:1 for the alcohol/acid molar ratio, 600 rpm for stirring speed and 7.8% for the catalyst concentration. Under these conditions, the reaction was scaled up in a 5 × 10−3 m3 stirred tank reactor. 1H–13C HMBC-NMR showed that the primary hydroxyl group of kojic acid was regioselectively esterified. The KMR has more lipophilicity than kojic acid and showed antioxidant activity that improves the oxidation stability of biodiesel. |
| first_indexed | 2024-03-06T08:32:15Z |
| format | Article |
| id | upm.eprints-35412 |
| institution | Universiti Putra Malaysia |
| last_indexed | 2024-03-06T08:32:15Z |
| publishDate | 2014 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | upm.eprints-354122016-01-06T03:44:40Z http://psasir.upm.edu.my/id/eprint/35412/ Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid El-Boulifi, Noureddin Ashari, Siti Efliza Serrano, Marta Aracil, Jose Martínez, Mercedes The aim of this work was the synthesis of a novel hydroxyl-fatty acid derivative of kojic acid rich in kojic acid monoricinoleate (KMR) which can be widely used in the cosmetic and food industry. The synthesis of KMR was carried out by lipase-catalysed esterification of ricinoleic and kojic acids in solvent-free system. Three immobilized lipases were tested and the best KMR yields were attained with Lipozyme TL IM and Novozym 435. Since Lipozyme TL IM is the cheapest, it was selected to optimize the reaction conditions. The optimal reaction conditions were 80 °C for the temperature, 1:1 for the alcohol/acid molar ratio, 600 rpm for stirring speed and 7.8% for the catalyst concentration. Under these conditions, the reaction was scaled up in a 5 × 10−3 m3 stirred tank reactor. 1H–13C HMBC-NMR showed that the primary hydroxyl group of kojic acid was regioselectively esterified. The KMR has more lipophilicity than kojic acid and showed antioxidant activity that improves the oxidation stability of biodiesel. Elsevier 2014-02-05 Article PeerReviewed El-Boulifi, Noureddin and Ashari, Siti Efliza and Serrano, Marta and Aracil, Jose and Martínez, Mercedes (2014) Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid. Enzyme and Microbial Technology, 55. pp. 128-132. ISSN 0141-0229; ESSN: 1879-0909 http://www.sciencedirect.com/science/article/pii/S0141022913002251 10.1016/j.enzmictec.2013.10.009 |
| spellingShingle | El-Boulifi, Noureddin Ashari, Siti Efliza Serrano, Marta Aracil, Jose Martínez, Mercedes Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid |
| title | Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid |
| title_full | Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid |
| title_fullStr | Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid |
| title_full_unstemmed | Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid |
| title_short | Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid |
| title_sort | solvent free lipase catalyzed synthesis of a novel hydroxyl fatty acid derivative of kojic acid |
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