Optimization of Lipase-Catalysed Synthesis and Characterization of Kojic Acid Esters

Kojic acid ester was successfully synthesized by esterification using lipase from Pseudomanas cepacia (Amano PS) as a biocatalyst in an organic media. The reaction mixture consisted of 90 mM of oleic acid, 360 mM of kojic acid and 0.15 g Amano PS in the presence of 2 mL of acetonitrile. The mixture...

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Main Author: Khamaruddin, Noor Hayati
Format: Thesis
Language:English
English
Published: 2007
Online Access:http://psasir.upm.edu.my/id/eprint/5001/1/FS_2007_18.pdf
http://psasir.upm.edu.my/id/eprint/5001/
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Institution: Universiti Putra Malaysia
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spelling my.upm.eprints.50012013-05-27T07:19:41Z http://psasir.upm.edu.my/id/eprint/5001/ Optimization of Lipase-Catalysed Synthesis and Characterization of Kojic Acid Esters Khamaruddin, Noor Hayati Kojic acid ester was successfully synthesized by esterification using lipase from Pseudomanas cepacia (Amano PS) as a biocatalyst in an organic media. The reaction mixture consisted of 90 mM of oleic acid, 360 mM of kojic acid and 0.15 g Amano PS in the presence of 2 mL of acetonitrile. The mixture was incubated at temperature of 50°C for 24 hour at shaking speed of 150 rpm. Lipozyme IM, Novozym 435, Pseudomonas cepacia lipase, Aspergillus niger, Candida rugosa and Eupergit C-Lipase were tested for their suitability as the enzyme in the reaction. Among the enzymes tested, lipase from Pseudomonas cepacia gave the highest enzyme activity (0.015 yield/μg protein content) and specific activity (3.738 x 10-6 mmol ester/min/mg protein content) in the synthesis. Oleic acid was found to be the best substrate to produce the ester but must be in the presence of acetonitrile as an organic solvent. The maximum percentage yield using Pseudomonas cepacia lipase at optimal condition was 44% without removal of water from the reaction mixture. From the optimization studies, kojic acid derivatives can be synthesized from palm oil and kojic acid, by Pseudomonas cepacia lipase (Amano PS). TLC analysis showed that kojic acid ester gave an Rf value of 0.28 in the TLC plate and a retention time of 31.752 min in the gas chromatogram. The product formation and the reactant disappearance were monitored by IR spectroscopy. A strong C=O stretching of the ester at 1746 cm-1 and weak absorption peak of O-H in the unreacted kojic acid indicated completion of the esterification reaction. The gas chromatography-mass spectrometry (GC-MS) analysis gave a molecular ion peak at m/z 478 which was due to the kojic acid ester. 1H-NMR and 13C-NMR spectral data confirmed the molecular structure of the kojic acid ester. 2007 Thesis NonPeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/5001/1/FS_2007_18.pdf Khamaruddin, Noor Hayati (2007) Optimization of Lipase-Catalysed Synthesis and Characterization of Kojic Acid Esters. Masters thesis, Universiti Putra Malaysia. English
institution Universiti Putra Malaysia
building UPM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Putra Malaysia
content_source UPM Institutional Repository
url_provider http://psasir.upm.edu.my/
language English
English
description Kojic acid ester was successfully synthesized by esterification using lipase from Pseudomanas cepacia (Amano PS) as a biocatalyst in an organic media. The reaction mixture consisted of 90 mM of oleic acid, 360 mM of kojic acid and 0.15 g Amano PS in the presence of 2 mL of acetonitrile. The mixture was incubated at temperature of 50°C for 24 hour at shaking speed of 150 rpm. Lipozyme IM, Novozym 435, Pseudomonas cepacia lipase, Aspergillus niger, Candida rugosa and Eupergit C-Lipase were tested for their suitability as the enzyme in the reaction. Among the enzymes tested, lipase from Pseudomonas cepacia gave the highest enzyme activity (0.015 yield/μg protein content) and specific activity (3.738 x 10-6 mmol ester/min/mg protein content) in the synthesis. Oleic acid was found to be the best substrate to produce the ester but must be in the presence of acetonitrile as an organic solvent. The maximum percentage yield using Pseudomonas cepacia lipase at optimal condition was 44% without removal of water from the reaction mixture. From the optimization studies, kojic acid derivatives can be synthesized from palm oil and kojic acid, by Pseudomonas cepacia lipase (Amano PS). TLC analysis showed that kojic acid ester gave an Rf value of 0.28 in the TLC plate and a retention time of 31.752 min in the gas chromatogram. The product formation and the reactant disappearance were monitored by IR spectroscopy. A strong C=O stretching of the ester at 1746 cm-1 and weak absorption peak of O-H in the unreacted kojic acid indicated completion of the esterification reaction. The gas chromatography-mass spectrometry (GC-MS) analysis gave a molecular ion peak at m/z 478 which was due to the kojic acid ester. 1H-NMR and 13C-NMR spectral data confirmed the molecular structure of the kojic acid ester.
format Thesis
author Khamaruddin, Noor Hayati
spellingShingle Khamaruddin, Noor Hayati
Optimization of Lipase-Catalysed Synthesis and Characterization of Kojic Acid Esters
author_facet Khamaruddin, Noor Hayati
author_sort Khamaruddin, Noor Hayati
title Optimization of Lipase-Catalysed Synthesis and Characterization of Kojic Acid Esters
title_short Optimization of Lipase-Catalysed Synthesis and Characterization of Kojic Acid Esters
title_full Optimization of Lipase-Catalysed Synthesis and Characterization of Kojic Acid Esters
title_fullStr Optimization of Lipase-Catalysed Synthesis and Characterization of Kojic Acid Esters
title_full_unstemmed Optimization of Lipase-Catalysed Synthesis and Characterization of Kojic Acid Esters
title_sort optimization of lipase-catalysed synthesis and characterization of kojic acid esters
publishDate 2007
url http://psasir.upm.edu.my/id/eprint/5001/1/FS_2007_18.pdf
http://psasir.upm.edu.my/id/eprint/5001/
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