Preparations of Betulinic Acid Derivatives

Betulinic acid, 3~hydroxy-lup20(29)-ene-28-oic acid is a pentacyclic triterpene. Esterification reactions of betulinic acid were investigated. Betulinic acid esters such as 3-0-succinyl-betulinic acid, 3-0-(2',2'-dimethylsucciny1)-betulinic acid, 3-0-(3',3'-dimethylsucciny1)-b...

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Main Author: Mohd Ali, Mohd Tajudin
Format: Thesis
Language:English
English
Published: 2004
Subjects:
Online Access:http://psasir.upm.edu.my/id/eprint/7080/
http://psasir.upm.edu.my/id/eprint/7080/1/FSAS_2004_5%28a%29.pdf
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author Mohd Ali, Mohd Tajudin
author_facet Mohd Ali, Mohd Tajudin
author_sort Mohd Ali, Mohd Tajudin
building UPM Institutional Repository
collection Online Access
description Betulinic acid, 3~hydroxy-lup20(29)-ene-28-oic acid is a pentacyclic triterpene. Esterification reactions of betulinic acid were investigated. Betulinic acid esters such as 3-0-succinyl-betulinic acid, 3-0-(2',2'-dimethylsucciny1)-betulinic acid, 3-0-(3',3'-dimethylsucciny1)-betulinic acid and 3-0-glutaryl-betulinic acid were prepared. Their structures were determined by spectroscopic methods. Optimization studies on the esterification reactions were carried out for betulinic acid with succinic anhydride and with 2',2'-dimethylsuccinic acid only. The effects of varying parameters such as the mole ratio, temperature, time course and mole of catalyst were investigated. Generally, the optimal conditions for preparing 3-0-succinyl-betulinic acid was obtained by mixing betulinic acid with succinic anhydride in a 1:8 ratio and refluxing in 0.124 mole of pyridine for 24 hours at a temperature of 115°C ; the optimal conditions for the preparation of 3-0-(2',2'-dimethylsucciny1)-betulinic acid was obtained by refluxing betulinic acid and Zf,2'-dimethylsuccinic acid in a 1:6 ratio with the presence of 0.124 mole of pyridine for 24 hours at a temperature of 85°C. The percentage conversions as detected by gas chromatography analysis were 53.5 and 56.2%, respectively.
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institution Universiti Putra Malaysia
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language English
English
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publishDate 2004
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spelling upm-70802023-11-21T08:23:00Z http://psasir.upm.edu.my/id/eprint/7080/ Preparations of Betulinic Acid Derivatives Mohd Ali, Mohd Tajudin Betulinic acid, 3~hydroxy-lup20(29)-ene-28-oic acid is a pentacyclic triterpene. Esterification reactions of betulinic acid were investigated. Betulinic acid esters such as 3-0-succinyl-betulinic acid, 3-0-(2',2'-dimethylsucciny1)-betulinic acid, 3-0-(3',3'-dimethylsucciny1)-betulinic acid and 3-0-glutaryl-betulinic acid were prepared. Their structures were determined by spectroscopic methods. Optimization studies on the esterification reactions were carried out for betulinic acid with succinic anhydride and with 2',2'-dimethylsuccinic acid only. The effects of varying parameters such as the mole ratio, temperature, time course and mole of catalyst were investigated. Generally, the optimal conditions for preparing 3-0-succinyl-betulinic acid was obtained by mixing betulinic acid with succinic anhydride in a 1:8 ratio and refluxing in 0.124 mole of pyridine for 24 hours at a temperature of 115°C ; the optimal conditions for the preparation of 3-0-(2',2'-dimethylsucciny1)-betulinic acid was obtained by refluxing betulinic acid and Zf,2'-dimethylsuccinic acid in a 1:6 ratio with the presence of 0.124 mole of pyridine for 24 hours at a temperature of 85°C. The percentage conversions as detected by gas chromatography analysis were 53.5 and 56.2%, respectively. 2004 Thesis NonPeerReviewed text en http://psasir.upm.edu.my/id/eprint/7080/1/FSAS_2004_5%28a%29.pdf Mohd Ali, Mohd Tajudin (2004) Preparations of Betulinic Acid Derivatives. Masters thesis, Universiti Putra Malaysia. Betulin Esterification English
spellingShingle Betulin
Esterification
Mohd Ali, Mohd Tajudin
Preparations of Betulinic Acid Derivatives
title Preparations of Betulinic Acid Derivatives
title_full Preparations of Betulinic Acid Derivatives
title_fullStr Preparations of Betulinic Acid Derivatives
title_full_unstemmed Preparations of Betulinic Acid Derivatives
title_short Preparations of Betulinic Acid Derivatives
title_sort preparations of betulinic acid derivatives
topic Betulin
Esterification
url http://psasir.upm.edu.my/id/eprint/7080/
http://psasir.upm.edu.my/id/eprint/7080/1/FSAS_2004_5%28a%29.pdf