Synthesis of piperine derivatives

The berries of black pepper (P. nigrum) are well known for its pungent smell and biting taste. Piperine which is one of the major amide present in P. nigrum contributes to the medicinal properties of the species. Extraction of the berries through maceration process followed by isolation of piperine...

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Main Author:	Muhamad Isa, Mardiana
Format:	Thesis
Language:	English
Published:	2012
Subjects:	Q Science (General)
Online Access:	http://eprints.utm.my/id/eprint/32819/5/MardianaMuhamadIsaMFS2012.pdf
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id	my-utm-ep.32819
record_format	uketd_dc
spelling	my-utm-ep.328192018-04-27T01:47:22Z Synthesis of piperine derivatives 2012-08 Muhamad Isa, Mardiana Q Science (General) The berries of black pepper (P. nigrum) are well known for its pungent smell and biting taste. Piperine which is one of the major amide present in P. nigrum contributes to the medicinal properties of the species. Extraction of the berries through maceration process followed by isolation of piperine via treatment with ethanolic potassium hydroxide successfully produced piperine (5-(1,3-benzodioxol- 5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one). Several chemical modifications have been carried out to derivatize piperine. Acetal cleavage has afforded 5-(3,4- dihydroxyphenyl)-1-(1-piperidinyl)-2,4-pentadien-1-one. Basic hydrolysis of piperine then afforded piperic acid (5-(1,3-benzodioxol-5-yl)-2,4-pentadienoic acid) which had been used as the precursor to synthesize an aliphatic amide (5-(1,3- benzodioxol-5-yl)-1-(n-butylamine)-2,4-pentadien-1-one), an ester (5-(1,3- benzodioxol-5-yl)ethyl-2,4-pentadienoate) and an acid (1,3-benzodioxol-1-yl)- methanoic acid). The pure piperine and derivatives were characterized by using infrared spectroscopy (IR), nuclear magnetic resonance (NMR) and mass spectrometry (MS). The screening for antimicrobial properties of the compounds were also carried out by using disc diffusion, minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods against Grampositive bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa). Piperine and all derivatives were found to be active towards Gram-positive bacteria with MIC value ranging from 225-900 µg/mL. 2012-08 Thesis http://eprints.utm.my/id/eprint/32819/ http://eprints.utm.my/id/eprint/32819/5/MardianaMuhamadIsaMFS2012.pdf application/pdf en public masters Universiti Teknologi Malaysia, Faculty of Science Faculty of Science
institution	Universiti Teknologi Malaysia
collection	UTM Institutional Repository
language	English
topic	Q Science (General)
spellingShingle	Q Science (General) Muhamad Isa, Mardiana Synthesis of piperine derivatives
description	The berries of black pepper (P. nigrum) are well known for its pungent smell and biting taste. Piperine which is one of the major amide present in P. nigrum contributes to the medicinal properties of the species. Extraction of the berries through maceration process followed by isolation of piperine via treatment with ethanolic potassium hydroxide successfully produced piperine (5-(1,3-benzodioxol- 5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one). Several chemical modifications have been carried out to derivatize piperine. Acetal cleavage has afforded 5-(3,4- dihydroxyphenyl)-1-(1-piperidinyl)-2,4-pentadien-1-one. Basic hydrolysis of piperine then afforded piperic acid (5-(1,3-benzodioxol-5-yl)-2,4-pentadienoic acid) which had been used as the precursor to synthesize an aliphatic amide (5-(1,3- benzodioxol-5-yl)-1-(n-butylamine)-2,4-pentadien-1-one), an ester (5-(1,3- benzodioxol-5-yl)ethyl-2,4-pentadienoate) and an acid (1,3-benzodioxol-1-yl)- methanoic acid). The pure piperine and derivatives were characterized by using infrared spectroscopy (IR), nuclear magnetic resonance (NMR) and mass spectrometry (MS). The screening for antimicrobial properties of the compounds were also carried out by using disc diffusion, minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods against Grampositive bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa). Piperine and all derivatives were found to be active towards Gram-positive bacteria with MIC value ranging from 225-900 µg/mL.
format	Thesis
qualification_level	Master's degree
author	Muhamad Isa, Mardiana
author_facet	Muhamad Isa, Mardiana
author_sort	Muhamad Isa, Mardiana
title	Synthesis of piperine derivatives
title_short	Synthesis of piperine derivatives
title_full	Synthesis of piperine derivatives
title_fullStr	Synthesis of piperine derivatives
title_full_unstemmed	Synthesis of piperine derivatives
title_sort	synthesis of piperine derivatives
granting_institution	Universiti Teknologi Malaysia, Faculty of Science
granting_department	Faculty of Science
publishDate	2012
url	http://eprints.utm.my/id/eprint/32819/5/MardianaMuhamadIsaMFS2012.pdf
_version_	1747816068154392576

Synthesis of piperine derivatives

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