Sustainable Synthesis of New Antioxidants from Hydroxytyrosol by Direct Biocatalytic Esterification in Ionic Liquids
Hydroxytyrosol (HT) is a nutraceutical compound, mainly found in the fruit, leaves and waste from the olive oil industry, known for exhibiting one of the highest antioxidant activities among molecules of natural origin. To harness this bioactivity in cosmetics, pharmaceuticals and the food industry,...
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MDPI AG
2024-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/29/21/5057 |
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| author | Susana Nieto Inmaculada Lozano Francisco J. Ruiz Jose F. Costa Rocio Villa Pedro Lozano |
| author_facet | Susana Nieto Inmaculada Lozano Francisco J. Ruiz Jose F. Costa Rocio Villa Pedro Lozano |
| author_sort | Susana Nieto |
| collection | DOAJ |
| description | Hydroxytyrosol (HT) is a nutraceutical compound, mainly found in the fruit, leaves and waste from the olive oil industry, known for exhibiting one of the highest antioxidant activities among molecules of natural origin. To harness this bioactivity in cosmetics, pharmaceuticals and the food industry, it is essential to modify the hydrophilicity of HT to enhance its compatibility with lipid-based mixtures. This chemical modification must be carried out with high selectivity to avoid compromising its radical scavenging activity. This work presents a highly efficient and selective approach to perform the biocatalytic esterification of free fatty acids (FFAs) of different alkyl chain lengths with HT in a reaction medium based on the SLIL [C<sub>12</sub>mim][NTf<sub>2</sub>]. By using a 1:2 (mol/mol) HT:FFA mixture of substrates, the HT-monoester derivative was obtained up to 77% yield after 2 h at 80 °C. The optimized molar ratio of substrates, combined with the ability to recover the SLIL for further reuse, significantly reduces waste accumulation compared to other reported strategies and results in a more sustainable approach as demonstrated by different green metrics. The antioxidant activity of HT-monoester products was fully maintained with respect to that presented by the natural HT, being stable for at least 3 months at 4 °C, as demonstrated by the DPPH and FRAP antioxidant analysis. |
| format | Article |
| id | doaj-art-abf72e29df574cca8227ec2d251afa9e |
| institution | OA Journals |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-10-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-abf72e29df574cca8227ec2d251afa9e2025-08-20T02:14:23ZengMDPI AGMolecules1420-30492024-10-012921505710.3390/molecules29215057Sustainable Synthesis of New Antioxidants from Hydroxytyrosol by Direct Biocatalytic Esterification in Ionic LiquidsSusana Nieto0Inmaculada Lozano1Francisco J. Ruiz2Jose F. Costa3Rocio Villa4Pedro Lozano5Departamento de Bioquímica y Biología Molecular B e Inmunología, Facultad de Química, Universidad de Murcia, E-30100 Murcia, SpainDepartamento de Bioquímica y Biología Molecular B e Inmunología, Facultad de Química, Universidad de Murcia, E-30100 Murcia, SpainDepartamento de Bioquímica y Biología Molecular B e Inmunología, Facultad de Química, Universidad de Murcia, E-30100 Murcia, SpainDepartamento de Bioquímica y Biología Molecular B e Inmunología, Facultad de Química, Universidad de Murcia, E-30100 Murcia, SpainDepartamento de Bioquímica y Biología Molecular B e Inmunología, Facultad de Química, Universidad de Murcia, E-30100 Murcia, SpainDepartamento de Bioquímica y Biología Molecular B e Inmunología, Facultad de Química, Universidad de Murcia, E-30100 Murcia, SpainHydroxytyrosol (HT) is a nutraceutical compound, mainly found in the fruit, leaves and waste from the olive oil industry, known for exhibiting one of the highest antioxidant activities among molecules of natural origin. To harness this bioactivity in cosmetics, pharmaceuticals and the food industry, it is essential to modify the hydrophilicity of HT to enhance its compatibility with lipid-based mixtures. This chemical modification must be carried out with high selectivity to avoid compromising its radical scavenging activity. This work presents a highly efficient and selective approach to perform the biocatalytic esterification of free fatty acids (FFAs) of different alkyl chain lengths with HT in a reaction medium based on the SLIL [C<sub>12</sub>mim][NTf<sub>2</sub>]. By using a 1:2 (mol/mol) HT:FFA mixture of substrates, the HT-monoester derivative was obtained up to 77% yield after 2 h at 80 °C. The optimized molar ratio of substrates, combined with the ability to recover the SLIL for further reuse, significantly reduces waste accumulation compared to other reported strategies and results in a more sustainable approach as demonstrated by different green metrics. The antioxidant activity of HT-monoester products was fully maintained with respect to that presented by the natural HT, being stable for at least 3 months at 4 °C, as demonstrated by the DPPH and FRAP antioxidant analysis.https://www.mdpi.com/1420-3049/29/21/5057lipasesbioactive moleculestailor synthesisneoteric solventsnutraceuticals |
| spellingShingle | Susana Nieto Inmaculada Lozano Francisco J. Ruiz Jose F. Costa Rocio Villa Pedro Lozano Sustainable Synthesis of New Antioxidants from Hydroxytyrosol by Direct Biocatalytic Esterification in Ionic Liquids Molecules lipases bioactive molecules tailor synthesis neoteric solvents nutraceuticals |
| title | Sustainable Synthesis of New Antioxidants from Hydroxytyrosol by Direct Biocatalytic Esterification in Ionic Liquids |
| title_full | Sustainable Synthesis of New Antioxidants from Hydroxytyrosol by Direct Biocatalytic Esterification in Ionic Liquids |
| title_fullStr | Sustainable Synthesis of New Antioxidants from Hydroxytyrosol by Direct Biocatalytic Esterification in Ionic Liquids |
| title_full_unstemmed | Sustainable Synthesis of New Antioxidants from Hydroxytyrosol by Direct Biocatalytic Esterification in Ionic Liquids |
| title_short | Sustainable Synthesis of New Antioxidants from Hydroxytyrosol by Direct Biocatalytic Esterification in Ionic Liquids |
| title_sort | sustainable synthesis of new antioxidants from hydroxytyrosol by direct biocatalytic esterification in ionic liquids |
| topic | lipases bioactive molecules tailor synthesis neoteric solvents nutraceuticals |
| url | https://www.mdpi.com/1420-3049/29/21/5057 |
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