Bromoindirubins: the synthesis and properties of minor components of Tyrian purple and the composition of the colorant from Nucella lapillus

Abstract

The identification of 6, 6′‐dibromoindirubin as a component of Tyrian purple has been confirmed by a practical synthesis. Two monobromoindirubins, which could be minor components, have also been synthesised. These compounds have been fully characterised by UV/vis, NMR, IR and MS data. However, the use of UV/vis absorption maxima in solution is shown to be an unreliable identification tool, being solvent dependent. MS cannot distinguish 6, 6′‐dibromoindirubin from 6, 6′‐dibromo‐indigotin, the major component; solution NMR is precluded by lack of solubility and the colorant is best characterised by HPLC. The first investigation of the composition of Tyrian purple from Nucella lapillus is reported.

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