Kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme RMIM and its rheological study
The synthesis of kojic acid derivative (KAD) from kojic and palmitic acid (C16:0) in the presence of immobilized lipase from Rhizomucor miehei (commercially known as Lipozyme RMIM), was studied using a shake flask system. Kojic acid is a polyfunctional heterocycles that acts as a source of nucleophi...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2018
|
| Online Access: | http://psasir.upm.edu.my/id/eprint/74790/1/Kinetics%20and%20optimization%20of%20lipophilic%20kojic%20acid%20derivative%20synthesis%20in%20polar%20aprotic%20solvent%20using%20lipozyme%20RMIM%20and%20its%20rheological%20study.pdf |
| _version_ | 1796979762603753472 |
|---|---|
| author | Ishak, Nurazwa Lajis, Ahmad Mohamad, Rosfarizan Ariff, Arbakariya Mohamed, Mohd Shamzi Halim, Murni Wasoh, Helmi |
| author_facet | Ishak, Nurazwa Lajis, Ahmad Mohamad, Rosfarizan Ariff, Arbakariya Mohamed, Mohd Shamzi Halim, Murni Wasoh, Helmi |
| author_sort | Ishak, Nurazwa |
| collection | UPM |
| description | The synthesis of kojic acid derivative (KAD) from kojic and palmitic acid (C16:0) in the presence of immobilized lipase from Rhizomucor miehei (commercially known as Lipozyme RMIM), was studied using a shake flask system. Kojic acid is a polyfunctional heterocycles that acts as a source of nucleophile in this reaction allowing the formation of a lipophilic KAD. In this study, the source of biocatalyst, Lipozyme RMIM, was derived from the lipase of Rhizomucor miehei immobilized on weak anion exchange macro-porous Duolite ES 562 by the adsorption technique. The effects of solvents, enzyme loading, reaction temperature, and substrate molar ratio on the reaction rate were investigated. In one-factor-at-a-time (OFAT) experiments, a high reaction rate (30.6 × 10−3 M·min−1) of KAD synthesis was recorded using acetone, enzyme loading of 1.25% (w/v), reaction time of 12 h, temperature of 50 °C and substrate molar ratio of 5:1. Thereafter, a yield of KAD synthesis was optimized via the response surface methodology (RSM) whereby the optimized molar ratio (fatty acid: kojic acid), enzyme loading, reaction temperature and reaction time were 6.74, 1.97% (w/v), 45.9 °C, and 20 h respectively, giving a high yield of KAD (64.47%). This condition was reevaluated in a 0.5 L stirred tank reactor (STR) where the agitation effects of two impellers; Rushton turbine (RT) and pitch-blade turbine (PBT), were investigated. In the STR, a very high yield of KAD synthesis (84.12%) was achieved using RT at 250 rpm, which was higher than the shake flask, thus indicating better mixing quality in STR. In a rheological study, a pseudoplastic behavior of KAD mixture was proposed for potential application in lotion formulation. |
| first_indexed | 2024-03-06T10:13:40Z |
| format | Article |
| id | upm.eprints-74790 |
| institution | Universiti Putra Malaysia |
| language | English |
| last_indexed | 2024-03-06T10:13:40Z |
| publishDate | 2018 |
| publisher | MDPI AG |
| record_format | dspace |
| spelling | upm.eprints-747902020-12-10T21:16:26Z http://psasir.upm.edu.my/id/eprint/74790/ Kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme RMIM and its rheological study Ishak, Nurazwa Lajis, Ahmad Mohamad, Rosfarizan Ariff, Arbakariya Mohamed, Mohd Shamzi Halim, Murni Wasoh, Helmi The synthesis of kojic acid derivative (KAD) from kojic and palmitic acid (C16:0) in the presence of immobilized lipase from Rhizomucor miehei (commercially known as Lipozyme RMIM), was studied using a shake flask system. Kojic acid is a polyfunctional heterocycles that acts as a source of nucleophile in this reaction allowing the formation of a lipophilic KAD. In this study, the source of biocatalyst, Lipozyme RMIM, was derived from the lipase of Rhizomucor miehei immobilized on weak anion exchange macro-porous Duolite ES 562 by the adsorption technique. The effects of solvents, enzyme loading, reaction temperature, and substrate molar ratio on the reaction rate were investigated. In one-factor-at-a-time (OFAT) experiments, a high reaction rate (30.6 × 10−3 M·min−1) of KAD synthesis was recorded using acetone, enzyme loading of 1.25% (w/v), reaction time of 12 h, temperature of 50 °C and substrate molar ratio of 5:1. Thereafter, a yield of KAD synthesis was optimized via the response surface methodology (RSM) whereby the optimized molar ratio (fatty acid: kojic acid), enzyme loading, reaction temperature and reaction time were 6.74, 1.97% (w/v), 45.9 °C, and 20 h respectively, giving a high yield of KAD (64.47%). This condition was reevaluated in a 0.5 L stirred tank reactor (STR) where the agitation effects of two impellers; Rushton turbine (RT) and pitch-blade turbine (PBT), were investigated. In the STR, a very high yield of KAD synthesis (84.12%) was achieved using RT at 250 rpm, which was higher than the shake flask, thus indicating better mixing quality in STR. In a rheological study, a pseudoplastic behavior of KAD mixture was proposed for potential application in lotion formulation. MDPI AG 2018-01 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/74790/1/Kinetics%20and%20optimization%20of%20lipophilic%20kojic%20acid%20derivative%20synthesis%20in%20polar%20aprotic%20solvent%20using%20lipozyme%20RMIM%20and%20its%20rheological%20study.pdf Ishak, Nurazwa and Lajis, Ahmad and Mohamad, Rosfarizan and Ariff, Arbakariya and Mohamed, Mohd Shamzi and Halim, Murni and Wasoh, Helmi (2018) Kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme RMIM and its rheological study. Molecules, 23 (3). pp. 1-26. ISSN 1420-3049; ESSN: 1431-5165 https://www.mdpi.com/1420-3049/23/2/501 10.3390/molecules23020501 |
| spellingShingle | Ishak, Nurazwa Lajis, Ahmad Mohamad, Rosfarizan Ariff, Arbakariya Mohamed, Mohd Shamzi Halim, Murni Wasoh, Helmi Kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme RMIM and its rheological study |
| title | Kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme RMIM and its rheological study |
| title_full | Kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme RMIM and its rheological study |
| title_fullStr | Kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme RMIM and its rheological study |
| title_full_unstemmed | Kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme RMIM and its rheological study |
| title_short | Kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme RMIM and its rheological study |
| title_sort | kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme rmim and its rheological study |
| url | http://psasir.upm.edu.my/id/eprint/74790/1/Kinetics%20and%20optimization%20of%20lipophilic%20kojic%20acid%20derivative%20synthesis%20in%20polar%20aprotic%20solvent%20using%20lipozyme%20RMIM%20and%20its%20rheological%20study.pdf |
| work_keys_str_mv | AT ishaknurazwa kineticsandoptimizationoflipophilickojicacidderivativesynthesisinpolaraproticsolventusinglipozymermimanditsrheologicalstudy AT lajisahmad kineticsandoptimizationoflipophilickojicacidderivativesynthesisinpolaraproticsolventusinglipozymermimanditsrheologicalstudy AT mohamadrosfarizan kineticsandoptimizationoflipophilickojicacidderivativesynthesisinpolaraproticsolventusinglipozymermimanditsrheologicalstudy AT ariffarbakariya kineticsandoptimizationoflipophilickojicacidderivativesynthesisinpolaraproticsolventusinglipozymermimanditsrheologicalstudy AT mohamedmohdshamzi kineticsandoptimizationoflipophilickojicacidderivativesynthesisinpolaraproticsolventusinglipozymermimanditsrheologicalstudy AT halimmurni kineticsandoptimizationoflipophilickojicacidderivativesynthesisinpolaraproticsolventusinglipozymermimanditsrheologicalstudy AT wasohhelmi kineticsandoptimizationoflipophilickojicacidderivativesynthesisinpolaraproticsolventusinglipozymermimanditsrheologicalstudy |