A new decomposition product of dihydroartemisinin.
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.
Dhooghe
L
L
Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B-2610 Antwerp, Belgium. Liene.Dhooghe@ua.ac.be
Van Miert
S
S
Jansen
H
H
Vlietinck
A
A
Pieters
L
L
D000962:Antimalarials / Q000737:chemistry*; D037621:Artemisinins / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D012717:Sesquiterpenes / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D000962:Antimalarials; D037621:Artemisinins; D007202:Indicators and Reagents; D012717:Sesquiterpenes; C039060:artenimol