Triumphalone, a diketone from the volatile oil of the leaves of Melaleuca triumphalis, and its spontaneous conversion into isotriumphalone

Phytochemistry. 2006 Sep;67(18):2085-9. doi: 10.1016/j.phytochem.2006.06.003. Epub 2006 Jul 20.

Abstract

The major component (35-65%) of the volatile oil obtained by steam distillation of the leaves of Melaleuca triumphalis has been identified as (rel)-1beta-pentyl-1alpha,6alpha-dihydroxy-3,3,5,5-tetramethylcyclohexa-2,4-dione (trivial name triumphalone). Relative stereochemistry was established by nuclear Overhauser experiments and X-ray studies on the 2-(3,5-dinitrobenzoic acid) derivative. The remainder of the oil was composed of mono- and sesquiterpene hydrocarbons and alcohols. On prolonged standing the presence of a rearrangement product of triumphalone was observed which was characterized as (rel)-1beta-pentyl-1alpha,3alpha-dihydroxy-4,4,6,6-tetramethylcyclohexa-2,5-dione (trivial name isotriumphalone), presumably arising from an acid catalyzed shift of the pentyl group from C-1 to C-2.

MeSH terms

  • Ketones / chemistry*
  • Ketones / isolation & purification
  • Ketones / metabolism
  • Magnetic Resonance Spectroscopy
  • Melaleuca / chemistry*
  • Molecular Structure
  • Oils, Volatile / chemistry
  • Oils, Volatile / isolation & purification*
  • Plant Leaves / chemistry*
  • Stereoisomerism

Substances

  • Ketones
  • Oils, Volatile
  • triumphalone