Styrene oxide

Styrene oxide
Names
	Preferred IUPAC name Phenyloxirane
	Other names Epoxystyrene; Styryl oxide; Phenylethylene oxide
Identifiers
CAS Number	96-09-3 ;
3D model ( JSmol)	Interactive image;
Beilstein Reference	108582
ChEBI	CHEBI:17907 ;
ChemSpider	7005;
ECHA InfoCard	100.002.252
EC Number	202-476-7;
Gmelin Reference	50213
KEGG	C02083 ;
PubChem CID	7276;
RTECS number	CZ9625000;
UNII	9QH06NGT6O ;
UN number	2810 3082
CompTox Dashboard (EPA)	DTXSID2021286 ;
	InChI InChI=1S/C8H8O/c1-2-4-7(5-3-1)8-6-9-8/h1-5,8H,6H2 Key: AWMVMTVKBNGEAK-UHFFFAOYSA-N;
	SMILES c1ccccc1C2CO2;
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H312, H319, H350
Precautionary statements	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). verify (what is ?) Infobox references

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 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

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

Styrene oxide is a main

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

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

^ Harold Hibbert and Pauline Burt (1941). "Styrene Oxide". Organic Syntheses.; Collective Volume, vol. 1, p. 494
^ Verfahren zur Herstellung von Phenylacetaldehyde, BASF-Patent DE3546372A1 vom 2. Juli 1987
ISBN 978-3-527-30673-2
.

^ EPA Styrene Oxide evaluation

PMID 809262.^{[permanent dead link}
]

Retrieved from "https://en.wikipedia.org/w/index.php?title=Styrene_oxide&oldid=1056043963"

[1] Harold Hibbert and Pauline Burt (1941). "Styrene Oxide". Organic Syntheses.; Collective Volume, vol. 1, p. 494

[2] Verfahren zur Herstellung von Phenylacetaldehyde, BASF-Patent DE3546372A1 vom 2. Juli 1987

[3] ISBN 978-3-527-30673-2
.

[4] EPA Styrene Oxide evaluation

[5] PMID 809262.^{[permanent dead link}
]

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