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Published on: April 27, 2017
A new decomposition product of dihydroartemisinin
L Dhooghe1, S Van Miert, H Jansen
1Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B-2610 Antwerp, Belgium. Liene.Dhooghe@ua.ac.be
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.
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