8. Molecular modelling analysis of metabolism of styrene

Fazlul Huq

School of Biomedical Sciences, Faculty of Health Sciences, The University of Sydney

Abstract:

Styrene is an industrial chemical used in the manufacture of plastics, synthetic rubbers and polyester resins. It is also an environmental contaminant present in some food, tobacco smoke and engine exhaust. Molecular modelling analyses based on molecular mechanics, semi-empirical and DFT calculations show that styrene-3,4-oxide has much larger values for total energy and heat of formation than styrene-7,8-oxide and styrene itself, indicating that the formation of styrene-3,4-oxide is energetically less favourable than that of styrene-7,8-oxide. Also, styrene-3,4-oxide is kinetically more labile than styrene-7,8-oxide so that it can react readily with cellular antioxidant glutathione, thus compromising the antioxidant status of the cell. Thus, styrene-3,4-oxide is considered to be more more toxic than styrene-7,8-oxide. However, it spontaneously rearranges itself to form relatively more stable 4-vinylphenol.

Key words: Styrene, styrene-7,8-oxide, toxicity, molecular modelling

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