Enantioselective metabolism of cumene

1. The enantioselective metabolism of cumene (isopropylbenzene) was studied in intact rabbits. 2. Of the total 2-phenyl-1-propanol formed metabolically, 90.3% was shown by h.p.l.c. to be (R)-(+)-2-phenyl-1-propanol. The corresponding values for (S)-(+)-2-phenylpropanoic acid and (R)-(-)-2-hydroxy-2-phenylpropanoic acid were 99.0 and 81.0%, respectively. 3. These results imply that firstly, preferential omega-hydroxylation occurs at the pro-S methyl group and secondly, the oxidation is followed by stereochemical inversion of (R)-(-)-2-phenylpropanol to the corresponding (S)-(+)-acid.