| Styrene oxide | |
|---|---|
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2-Phenyloxirane |
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Other names
Phenyloxirane; Epoxystyrene; Styryl oxide; Phenylethylene oxide |
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| Identifiers | |
| CAS number | 96-09-3 |
| PubChem | 7276 |
| KEGG | C02083 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C8H8O |
| Molar mass | 120.15 g/mol |
| Appearance | Colorless to light yellow liquid |
| Density | 1.052 g/mL |
| Melting point |
-37 °C, 236 K, -35 °F |
| Boiling point |
194 °C, 467 K, 381 °F |
| Hazards | |
| MSDS | Oxford University MSDS |
| EU classification | Harmful (XN); Corrosive (C) |
| R-phrases | R20 R22 R34 R36 R37 R38 |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Styrene oxide is an epoxide derived from styrene. It may be prepared by epoxidation of styrene with peroxybenzoic acid, in the Prilezhaev reaction:[1]
Styrene oxide is a main metabolite of styrene in humans or animals, resulting from oxidation by cytochrome P450. It is considered toxic, mutagenic, and possibly carcinogenic. Styrene oxide is subsequently hydrolyzed in vivo to styrene glycol by epoxide hydrolase.[2]
Styrene oxide has a chiral center and thus two enantiomers. It has been reported that the two enantiomers had different toxicokinetics and toxicity. It was reported that the (R)-styrene oxide was preferentially formed in mice, especially in the lung, whereas the (S)-styrene oxide was preferentially generated in rats. In human volunteers, the cumulative excretion of the (S)-enantiomer of styrene glycol and mendelic acid were higher than the R form after exposure to styrene. In human liver microsomes, cytochrome P450-mediated styrene oxidation showed the production of more S enantiomer relative to the R enantiomer. It was also found that (S)-styrene oxide was preferentially hydrolyzed than the R enantiomer in human liver microsomes. Animal studies have shown that the (R)-enantiomer of styrene oxide was more toxic than the (S)-enantiomer in mice.