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Note | Regular issue | Vol 78, No. 7, 2009, pp.1823-1829
Published online, 31st March, 2009
DOI: 10.3987/COM-09-11679
Relative Stability of Cryptolepinone and Hydroxycryptolepine

Masahiro Kataoka* and Tsuguo Sato

*Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

The relative stability between cryptolepinone and 11-hydroxycryptolepine in solvents has been investigated by use of semiempirical molecular orbital and hybrid-density functional methods. The results have predicted that only cryptolepinone exists in all solvents examined (pyridine, acetone, MeOH, MeCN and DMSO), disagreeing with the experimental findings in which in MeOH and MeCN both cryptolepinone and 11-hydroxycryptolep are present. This disagreement suggests that MeOH and MeCN solutions include chemical species other than 11-hydroxycryptolepin.