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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...

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Main Authors: Ishak, Nurazwa, Lajis, Ahmad, Mohamad, Rosfarizan, Ariff, Arbakariya, Mohamed, Mohd Shamzi, Halim, Murni, Wasoh, Helmi
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
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spelling oai:psasir.upm.edu.my:74790 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
institution UPM IR
collection UPM IR
language English
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.
format Article
author Ishak, Nurazwa
Lajis, Ahmad
Mohamad, Rosfarizan
Ariff, Arbakariya
Mohamed, Mohd Shamzi
Halim, Murni
Wasoh, Helmi
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
author_facet Ishak, Nurazwa
Lajis, Ahmad
Mohamad, Rosfarizan
Ariff, Arbakariya
Mohamed, Mohd Shamzi
Halim, Murni
Wasoh, Helmi
author_sort Ishak, Nurazwa
title 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_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_sort kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme rmim and its rheological study
publisher MDPI AG
publishDate 2018
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
_version_ 1819299190077915136
score 13.4562235

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