Stereochemistry of styrene biotransformation*

Abstract

Metabolism of styrene, an important industrial monomer, is reviewed. Attention is focused on the stereoselectivity of its oxidation to 7,8-styrene oxide as well as on further stereoselective biotransformation by hydrolytic and mercapturic acid pathway. Toxic effects such as mutagenicity, genotoxicity, hepatotoxicity, and pneumotoxicity may be related to the ratio of styrene oxide enantiomers at the target site. In rats formation of the less mutagenic (S)-styrene oxide and a faster detoxication of the (R)-enantiomer is favored. In mice metabolic activation of styrene favors the formation of (R)-styrene oxide but this more toxic enantiomer is detoxified faster, so that a nearly racemic styrene oxide results. Stereochemistry of biotransformation can contribute to the species differences in toxicity but can hardly be interpreted as a crucial factor. Due to lack of relevant data the stereochemistry of human metabolism cannot be interpreted in relation to the toxic effects.