A new decomposition product of dihydroartemisinin.

Die Pharmazie
L DhoogheL Pieters

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.

Citations

Jul 24, 2010·Malaria Journal·Frans Herwig Jansen

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