Next Article in Journal
Palladium(II)-Catalyzed othro-C–H-Benzoxylation of 2-Arylpyridines by Oxidative Coupling with Aryl Acylperoxides
Next Article in Special Issue
Intravenous and Subcutaneous Toxicity and Absorption Kinetics in Mice and Dogs of the Antileishmanial Triterpene Saponin PX-6518
Previous Article in Journal
Chemical Methods for Peptide and Protein Production
Previous Article in Special Issue
Metabolomic Analysis of Methyl Jasmonate-Induced Triterpenoid Production in the Medicinal Herb Centella asiatica (L.) Urban
Molecules 2013, 18(4), 4389-4402; doi:10.3390/molecules18044389
Article

Preparation, Purification and Regioselective Functionalization of Protoescigenin—The Main Aglycone of Escin Complex

1
, 1
, 1
, 1
, 2
, 3
, 1,4
, 1
, 2, 3
 and 1,*
1 Pharmaceutical Research Institute, Rydygiera 8, Warszawa 01-793, Poland 2 Department of General and Nutritional Biochemistry, Warsaw Medical University, Żwirki i Wigury 61, Warszawa 02-091, Poland 3 Department of Chemistry, Warsaw University, Pasteura 1, Warszawa 02-093, Poland 4 Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, Warszawa 01-224, Poland
* Author to whom correspondence should be addressed.
Received: 8 February 2013 / Revised: 1 April 2013 / Accepted: 9 April 2013 / Published: 15 April 2013
(This article belongs to the Special Issue Triterpenes and Triterpenoids)
Download PDF [984 KB, 18 June 2014; original version 18 June 2014]

Abstract

A two-step chemical process for controlled degradation of escin, affording a mixture of olean-12-ene sapogenins, was elaborated and scaled up. The main component of the mixture—protoescigenin—was isolated and purified, in the form of its corresponding monohydrate, without resource to chromatographic methods. This material was further converted into the high purity 3,24;16,22-di-O,O-isopropylidene derivative in a validated large scale laboratory process.
Keywords: escin; protoescigenin hydrates; protoescigenin diacetonide; polymorphism; X-ray crystallography escin; protoescigenin hydrates; protoescigenin diacetonide; polymorphism; X-ray crystallography
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

Gruza, M.M.; Jatczak, K.; Zagrodzki, B.; Łaszcz, M.; Koziak, K.; Malińska, M.; Cmoch, P.; Giller, T.; Zegrocka-Stendel, O.; Woźniak, K.; Grynkiewicz, G. Preparation, Purification and Regioselective Functionalization of Protoescigenin—The Main Aglycone of Escin Complex. Molecules 2013, 18, 4389-4402.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert