Enzymatic syntheses, characterizations and applications of fatty hydroxamic acid derivatives from canola and palm oils

Fatty hydroxamic acids and derivatives have attracted many researches due to their pharmaceutical and analytical applications. They have been widely applied as food additives, growth factors, antibacterial agents, fungicides, tumor inhibitors, enzyme inhibitors and metal chelators. A common method...

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Main Author:	Jahangirian, Hossein
Format:	Thesis
Language:	English
Published:	2012
Subjects:	Hydroxamic acids Canola Enzymatic analysis
Online Access:	http://psasir.upm.edu.my/id/eprint/31942/1/FS%202012%2041R.pdf
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spelling	my-upm-ir.319422015-01-19T07:55:33Z Enzymatic syntheses, characterizations and applications of fatty hydroxamic acid derivatives from canola and palm oils 2012-05 Jahangirian, Hossein Fatty hydroxamic acids and derivatives have attracted many researches due to their pharmaceutical and analytical applications. They have been widely applied as food additives, growth factors, antibacterial agents, fungicides, tumor inhibitors, enzyme inhibitors and metal chelators. A common method for the preparation of hydroxamic acids and their derivatives is via reaction of hydroxylamine or their derivatives with alkyl esters or activated carboxylic acids. However these reactions often contain many steps and require expensive chemicals. In this study, four types of N-substituted fatty hydroxamic acids as the following were synthesized. Phenyl fatty hydroxamic acids (PFHAs), synthesized by reaction of canola oil, palm kernel oil or palm stearin with N-phenyl hydroxylamine (N-PHA). Methyl fatty hydroxamic acids (MFHAs), synthesized by reaction of palm kernel oil and Nmethyl hydroxylamine (N-MHA). Isopropyl fatty hydroxamic acids (IPFHAs), synthesized by reaction of palm kernel oil and N- isopropyl hydroxylamine (NIPHA). Benzyl fatty hydroxamic acids (BFHAs), synthesized by reaction of palm kernel oil and N-benzyl hydroxylamine (N-BHA). The reactions were carried out in a sealed flask, incubated in water bath shaker at 39°C for 72 hours and catalyzed by immobilized lipase (Lipozyme TL IM or RM IM). The products were then separated by filtration, solvent extraction followed by evaporation of the solvent. The products were characterized by The FT-IR and 1H NMR spectroscopies, CHN elemental analysis and qualitative color test with Cu(II), Fe(III) and V(V) ions. The products as chelating agents were used for extraction of Cu(II) or Fe(III) ions from samples containing mixture of metal ions in aqueous solution. The products and their copper complexes were also evaluated for antibacterial activity on Escherichia coli (E. Coli) and Staphylococcus aureus (S. Aureus) and antifungal activity on Candida parapsilosis (C. parapsilosis), Candida albicans (C. albicans) and Aspergillus fumigatus (A. fumigatus) using disk and well diffusion methods. The conversion percentage of phenyl hydroxylaminolysis of the two different commercial canola oils (Ladan and Krystal brands), palm stearin oil and palm kernel oil were 55.6, 52.2, 51.4 and 49.7 %, respectively. In addition the conversion percentage of methyl hydroxylaminolysis, isopropyl hydroxylaminolysis and benzyl hydroxylaminolysis of the commercial palm kernel oil were 77.8, 65.4 and 61.7 %, respectively. The FTIR and 1H NMR spectroscopic data, CHN elemental analysis and qualitative color test on the purified products confirmed the existence of PFHAs, MFHAs, IPFHAs and BFHAs. Hydroxamic acids Canola Enzymatic analysis 2012-05 Thesis http://psasir.upm.edu.my/id/eprint/31942/ http://psasir.upm.edu.my/id/eprint/31942/1/FS%202012%2041R.pdf application/pdf en public phd doctoral Universiti Putra Malaysia Hydroxamic acids Canola Enzymatic analysis Faculty of Science
institution	Universiti Putra Malaysia
collection	PSAS Institutional Repository
language	English
topic	Hydroxamic acids Canola Enzymatic analysis
spellingShingle	Hydroxamic acids Canola Enzymatic analysis Jahangirian, Hossein Enzymatic syntheses, characterizations and applications of fatty hydroxamic acid derivatives from canola and palm oils
description	Fatty hydroxamic acids and derivatives have attracted many researches due to their pharmaceutical and analytical applications. They have been widely applied as food additives, growth factors, antibacterial agents, fungicides, tumor inhibitors, enzyme inhibitors and metal chelators. A common method for the preparation of hydroxamic acids and their derivatives is via reaction of hydroxylamine or their derivatives with alkyl esters or activated carboxylic acids. However these reactions often contain many steps and require expensive chemicals. In this study, four types of N-substituted fatty hydroxamic acids as the following were synthesized. Phenyl fatty hydroxamic acids (PFHAs), synthesized by reaction of canola oil, palm kernel oil or palm stearin with N-phenyl hydroxylamine (N-PHA). Methyl fatty hydroxamic acids (MFHAs), synthesized by reaction of palm kernel oil and Nmethyl hydroxylamine (N-MHA). Isopropyl fatty hydroxamic acids (IPFHAs), synthesized by reaction of palm kernel oil and N- isopropyl hydroxylamine (NIPHA). Benzyl fatty hydroxamic acids (BFHAs), synthesized by reaction of palm kernel oil and N-benzyl hydroxylamine (N-BHA). The reactions were carried out in a sealed flask, incubated in water bath shaker at 39°C for 72 hours and catalyzed by immobilized lipase (Lipozyme TL IM or RM IM). The products were then separated by filtration, solvent extraction followed by evaporation of the solvent. The products were characterized by The FT-IR and 1H NMR spectroscopies, CHN elemental analysis and qualitative color test with Cu(II), Fe(III) and V(V) ions. The products as chelating agents were used for extraction of Cu(II) or Fe(III) ions from samples containing mixture of metal ions in aqueous solution. The products and their copper complexes were also evaluated for antibacterial activity on Escherichia coli (E. Coli) and Staphylococcus aureus (S. Aureus) and antifungal activity on Candida parapsilosis (C. parapsilosis), Candida albicans (C. albicans) and Aspergillus fumigatus (A. fumigatus) using disk and well diffusion methods. The conversion percentage of phenyl hydroxylaminolysis of the two different commercial canola oils (Ladan and Krystal brands), palm stearin oil and palm kernel oil were 55.6, 52.2, 51.4 and 49.7 %, respectively. In addition the conversion percentage of methyl hydroxylaminolysis, isopropyl hydroxylaminolysis and benzyl hydroxylaminolysis of the commercial palm kernel oil were 77.8, 65.4 and 61.7 %, respectively. The FTIR and 1H NMR spectroscopic data, CHN elemental analysis and qualitative color test on the purified products confirmed the existence of PFHAs, MFHAs, IPFHAs and BFHAs.
format	Thesis
qualification_name	Doctor of Philosophy (PhD.)
qualification_level	Doctorate
author	Jahangirian, Hossein
author_facet	Jahangirian, Hossein
author_sort	Jahangirian, Hossein
title	Enzymatic syntheses, characterizations and applications of fatty hydroxamic acid derivatives from canola and palm oils
title_short	Enzymatic syntheses, characterizations and applications of fatty hydroxamic acid derivatives from canola and palm oils
title_full	Enzymatic syntheses, characterizations and applications of fatty hydroxamic acid derivatives from canola and palm oils
title_fullStr	Enzymatic syntheses, characterizations and applications of fatty hydroxamic acid derivatives from canola and palm oils
title_full_unstemmed	Enzymatic syntheses, characterizations and applications of fatty hydroxamic acid derivatives from canola and palm oils
title_sort	enzymatic syntheses, characterizations and applications of fatty hydroxamic acid derivatives from canola and palm oils
granting_institution	Universiti Putra Malaysia
granting_department	Faculty of Science
publishDate	2012
url	http://psasir.upm.edu.my/id/eprint/31942/1/FS%202012%2041R.pdf
_version_	1747811637071446016

Enzymatic syntheses, characterizations and applications of fatty hydroxamic acid derivatives from canola and palm oils

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