Oxygen acts on colupulone in petroleum at 60° to give 5-hydroxy-5-isobutyryl-3,3-bis-(3-methylbut-2-enyl)-cyclopentane-1,2,4-trione, which we find present in old hops. Cohulupone is evidently an intermediate, but the new product appears not to be an intermediate in the oxidation of cohulupone to hulupinic acid.
J. Coates, D. R. J. Laws and J. A. Elvidge, J. Chem. Soc., Perkin Trans. 1, 1974, 36 DOI: 10.1039/P19740000036
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