Styrene oxide

Summary

Styrene oxide is an epoxide derived from styrene. It can be prepared by epoxidation of styrene with peroxybenzoic acid, in the Prilezhaev reaction:[1]

Styrene oxide
Names
Preferred IUPAC name
Phenyloxirane
Other names
Epoxystyrene; Styryl oxide; Phenylethylene oxide
Identifiers
  • 96-09-3 checkY
3D model (JSmol)
  • Interactive image
108582
ChEBI
  • CHEBI:17907 ☒N
ChemSpider
  • 7005
ECHA InfoCard 100.002.252 Edit this at Wikidata
EC Number
  • 202-476-7
50213
KEGG
  • C02083 checkY
  • 7276
RTECS number
  • CZ9625000
UNII
  • 9QH06NGT6O checkY
UN number 2810 3082
  • DTXSID2021286 Edit this at Wikidata
  • InChI=1S/C8H8O/c1-2-4-7(5-3-1)8-6-9-8/h1-5,8H,6H2
    Key: AWMVMTVKBNGEAK-UHFFFAOYSA-N
  • c1ccccc1C2CO2
Properties
C8H8O
Molar mass 120.151 g·mol−1
Appearance Colorless to light yellow liquid
Density 1.052 g/mL
Melting point −37 °C (−35 °F; 236 K)
Boiling point 194 °C (381 °F; 467 K)
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Danger
H312, H319, H350
P201, P202, P264, P280, P281, P302+P352, P305+P351+P338, P308+P313, P312, P322, P337+P313, P363, P405, P501
Safety data sheet (SDS) Oxford University MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Styrene oxide is slightly soluble in water. A trace amount of acid in water causes hydrolysis to racemic phenylethyleneglycol via a benzylic cation. If the amount of water is not sufficient, acid-catalyzed isomerization for phenylacetaldehyde will occur.[2]

Styrene oxide in the body is metabolized to mandelic acid, phenylglyoxylic acid, benzoic acid and hippuric acid.

Hydrogenation of styrene oxide affords phenethyl alcohol.[3]

Stereospecific reactions edit

Since styrene oxide has a chiral center at the benzylic carbon atom, there are (R)-styrene oxide and (S)-styrene oxide. If optically pure reagent is used, only one optically pure compound will be obtained.

Toxicology edit

Styrene oxide is a main metabolite of styrene in humans or animals, resulting from oxidation by cytochrome P450. It is considered possibly carcinogenic from gavaging significant amounts into mice and rats.[4] Styrene oxide is subsequently hydrolyzed in vivo to styrene glycol by epoxide hydrolase.[5]

Styrene oxide has a chiral center and thus two enantiomers. It has been reported that the two enantiomers had different toxicokinetics and toxicity[citation needed]. 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 mandelic 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.

References edit

  1. ^ Harold Hibbert and Pauline Burt (1941). "Styrene Oxide". Organic Syntheses; Collected Volumes, vol. 1, p. 494.
  2. ^ Verfahren zur Herstellung von Phenylacetaldehyde, BASF-Patent DE3546372A1 vom 2. Juli 1987
  3. ^ Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst (2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_141. ISBN 978-3-527-30673-2.
  4. ^ EPA Styrene Oxide evaluation
  5. ^ Kenneth C. Liebman (1975). "Metabolism and toxicity of styrene" (PDF). Environmental Health Perspectives. 11: 115–119. doi:10.2307/3428333. JSTOR 3428333. PMC 1475194. PMID 809262.[permanent dead link]