In growing cultures of the fungus Beauveria bassiana (ATCC 7159) the incubation of 4-(4′-hydroxyphenyl)but-3-en-2-one (p-hydroxybenzylidenacetone, 3), of 4-(4′-hydroxyphenyl)butan-2-one (raspberry ketone, 1), and of the S and R,S forms of 4-(4′-hydroxyphenyl)butan-2-ol (2) yields 2-(4′-hydroxyphenyl)ethanol (tyrosol, 4) as a final product. The experiments support the view that the actual substrate for the Baeyer-Villiger-type degradation is raspberry ketone (1) and that there is a kinetic preference in the microbial enzymatic system for the oxidation to 1 of the S form of the 4-(4′-hydroxyphenyl)butan-2-ol (2).
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