A new decomposition product of dihydroartemisinin

Pharmazie. 2007 Dec;62(12):900-1. doi: 10.1055/s-2007-987115.

Abstract

After prolonged storage, samples of dihydroartemisinin were found to contain a decomposition product with a molecular weight of 238, as evidenced by MS analysis, the formation of which was accelerated by heating at 60 degrees C for several days. This decomposition product was isolated and identified as 2-(3-oxobutyl)-3-methyl-6-(2-propanal)-cyclohexanon, known to be formed by thermolysis of dihydroartemisinin at 190 degrees C. However, during work-up of this compound a hitherto unknown decomposition product of dihydroartemisinin with a molecular weight of 210 was obtained and identified by 1H, 13C and two-dimensional NMR spectroscopy as 2-(3-oxobutyl)-3-methyl-6-ethyl-cyclohexanon. Most probably this product was formed by oxidation of the aldehyde functionality of the former decomposition product and subsequent decarboxylation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / chemistry*
  • Artemisinins / chemistry*
  • Chromatography, Thin Layer
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Sesquiterpenes / chemistry*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Antimalarials
  • Artemisinins
  • Indicators and Reagents
  • Sesquiterpenes
  • artenimol