Chloroethylene oxide

Chloroethylene oxide
Names
	Other names 2-chlorooxirane, CEO
Identifiers
CAS Number	7763-77-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29129;
ChemSpider	22880;
KEGG	C20303;
PubChem CID	24472;
CompTox Dashboard (EPA)	DTXSID10998848 ;
	InChI InChI=1S/C2H3ClO/c3-2-1-4-2/h2H,1H2 Key: WBNCHVFLFSFIGK-UHFFFAOYSA-N;
	SMILES C1C(O1)Cl;
Properties
Chemical formula	C2H3ClO
Molar mass	78.50 g·mol−1
Appearance	colorless liquid
Boiling point	40–55 °C (104–131 °F; 313–328 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chloroethylene oxide is the organic compound with the formula ClC₂H₃O. It is the epoxide of vinyl chloride. The compound is rarely observed, but it is widely proposed as a metabolite of vinyl chloride, formed by the action of cytochrome-P450. It is significant because it causes DNA alkylation. It isomerizes to chloroacetaldehyde, which modifies adenosine residues by conversion to 1,N⁶-ethenodeoxyadenosine (εdA).[1][2]

References

Pandya, Gagan A.; Moriya, Masaaki (1996). "1,N⁶-Ethenodeoxyadenosine, a DNA Adduct Highly Mutagenic in Mammalian Cells". Biochemistry. 35 (35): 11487–11492. doi:10.1021/bi960170h. PMID 8784204.
Clewell, Harvey J.; Gentry, P.Robinan; Gearhart, Jeffrey M.; Allen, Bruce C.; Andersen, Melvin E. (2001). "Comparison of cancer risk estimates for vinyl chloride using animal and human data with a PBPK model". Science of the Total Environment. 274 (1–3): 37–66. doi:10.1016/s0048-9697(01)00730-6. PMID 11453305. S2CID 43793528.

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[1] Pandya, Gagan A.; Moriya, Masaaki (1996). "1,N⁶-Ethenodeoxyadenosine, a DNA Adduct Highly Mutagenic in Mammalian Cells". Biochemistry. 35 (35): 11487–11492. doi:10.1021/bi960170h. PMID 8784204.

[2] Clewell, Harvey J.; Gentry, P.Robinan; Gearhart, Jeffrey M.; Allen, Bruce C.; Andersen, Melvin E. (2001). "Comparison of cancer risk estimates for vinyl chloride using animal and human data with a PBPK model". Science of the Total Environment. 274 (1–3): 37–66. doi:10.1016/s0048-9697(01)00730-6. PMID 11453305. S2CID 43793528.