Chemistry:Chloroethylene oxide

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Chloroethylene oxide
Chloroethyleneoxide.svg
Names
Other names
2-chlorooxirane, CEO
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
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

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

  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.