Next Article in Journal
Pumpkin (Cucurbita moschata) Fruit Extract Improves Physical Fatigue and Exercise Performance in Mice
Previous Article in Journal
10-Acetylirciformonin B, A Sponge Furanoterpenoid, Induces DNA Damage and Apoptosis in Leukemia Cells
Article Menu

Article Versions

Export Article

Open AccessArticle
Molecules 2012, 17(10), 11849-11863; doi:10.3390/molecules171011849

A Practical Synthesis of Betulonic Acid Using Selective Oxidation of Betulin on Aluminium Solid Support

1
Department of Pharmaceutical Chemistry, Nizhny Novgorod State Medical Academy, Minin sq. 10/1, Nizhny Novgorod 603-000, Russia
2
Department of Chemistry, N.P. Ogarev Mordovian State University, Mironov St. 3-274, Saransk 430-005, Russia
3
Department of Chemistry, Nizhny Novgorod State University, Kuibishev St. 17-25, Nizhny Novgorod 603-950, Russia
*
Author to whom correspondence should be addressed.
Received: 10 August 2012 / Revised: 23 September 2012 / Accepted: 24 September 2012 / Published: 9 October 2012
(This article belongs to the Section Organic Synthesis)
Download PDF [311 KB, uploaded 18 June 2014]

Abstract

The room temperature oxidation of betulin by Cr(VI) compounds in aqueous acetone on solid supports such as alumina, zeolites and silica gel has been studied. The oxidation on alumina support leaded to a single product—betulonic acid—in quantitative yield. One hundred percent selective oxidation during 30 min of betulin up to betulonic aldehyde was determined when silica gel support was used. The oxidation of betulin using zeolites as a support gives a mixture of betulonic acid and aldehyde in a 2:1 ratio. It is proposed the selective oxidation up to betulonic acid is due to the influence of Al3+-ions.
Keywords: oxidation on alumina; betulin; betulonic acid; protection of double bond by Al3+-ions oxidation on alumina; betulin; betulonic acid; protection of double bond by Al3+-ions
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Melnikova, N.; Burlova, I.; Kiseleva, T.; Klabukova, I.; Gulenova, M.; Kislitsin, А.; Vasin, V.; Tanaseichuk, B. A Practical Synthesis of Betulonic Acid Using Selective Oxidation of Betulin on Aluminium Solid Support. Molecules 2012, 17, 11849-11863.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top