Chloroethylene oxide

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]

Chloroethylene oxide
Names
Other names
2-chlorooxirane, CEO
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C2H3ClO/c3-2-1-4-2/h2H,1H2
    Key: WBNCHVFLFSFIGK-UHFFFAOYSA-N
  • C1C(O1)Cl
Properties
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

References

  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.
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