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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 383788733
| Watchedfields = changed
⚫ | Name = Mutagen X
⚫ | verifiedrevid = 433354158
⚫ | ImageFile = MX structure.png
⚫ | Name = Mutagen X
⚫ <!-- | ImageSize = 150px -->
⚫ | ImageFile = MX structure.png
| ImageName =
⚫ | ImageSize = 150
⚫ | IUPACName = 3-Chloro-4-(dichloromethyl)-5-<br />hydroxy-5''H''-furan-2-one
| ImageAlt = Skeletal formula of mutagen X
⚫ | OtherNames = Mutagen X<br />MX
| ImageFile1 = Mutagen-X-3D-spacefill.png
⚫ | Section1 = {{Chembox Identifiers
| ImageSize1 = 150
⚫ | CASNo = 77439-76-0
| ImageAlt1 = Space-filling model of the mutagen X molecule
⚫ | IUPACName = 3-Chloro-4-(dichloromethyl)-5-<wbr />hydroxy-5''H''-furan-2-one
⚫ | OtherNames = Mutagen X<br />MX
⚫ |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
⚫ | CASNo = 77439-76-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SSD7YR4366
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C19205 | KEGG = C19205
| SMILES = O=C1OC(O)C(C(Cl)Cl)=C1Cl | SMILES = O=C1OC(O)C(C(Cl)Cl)=C1Cl
| EINECS = 253-575-7
| PubChem = 53665
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 48451
| InChI = 1/C5H3Cl3O3/c6-2-1(3(7)8)4(9)11-5(2)10/h3-4,9H
| InChIKey = WNTRMRXAGJOLCU-UHFFFAOYAU
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C5H3Cl3O3/c6-2-1(3(7)8)4(9)11-5(2)10/h3-4,9H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = WNTRMRXAGJOLCU-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>5</sub>H<sub>3</sub>Cl<sub>3</sub>O<sub>3</sub> | Formula = C<sub>5</sub>H<sub>3</sub>Cl<sub>3</sub>O<sub>3</sub>
| MolarMass = 217.43 g/mol | MolarMass = 217.43 g/mol
| Density = | Density =
| MeltingPt = | MeltingPt =
}} }}
}} }}


'''Mutagen X''' (MX), or 3-chloro-4-(dichloromethyl)-5-hydroxy-5''H''-furan-2-one, is a byproduct of the disinfection of water by ]. MX is produced by reaction of chlorine with natural ]s. '''Mutagen X''' (MX), or 3-chloro-4-(dichloromethyl)-5-hydroxy-5''H''-furan-2-one, is a byproduct of the disinfection of water by ]. MX is produced by reaction of chlorine with natural ]s.


MX is found in chlorinated drinking water all over the world and is an environmental carcinogen that is known to cause several types of cancer in rats when present in large enough concentrations.<ref>{{cite journal | title = Oxidative stress and DNA damage induced by a drinking-water chlorination disinfection byproduct 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) in mice | author = Yuan, Jing; Liu, Hui; Zhou, Li-Hong; Zou, Ya-Lin; Lu, Wen-Qing | journal = Mutation Research | year = 2006 | volume = 609 | issue = 2 | pages = 129–136 | pmid = 16952480 | doi = 10.1016/j.mrgentox.2006.05.011}}</ref> It is listed by the ] as a ] ] meaning it is "possibly carcinogenic to humans". Although the concentration of MX in drinking water is typically 100- to 1000-fold lower than other common byproducts of water chlorination such as ]s, MX might play a role in the increased cancer risks that have been associated with the consumption of chlorinated water because of its potency in inducing DNA damage.<ref>{{cite journal | title = Carcinogenicity of the chlorination disinfection by-product MX | author = McDonald, Thomas A.; Komulainen, Hannu | journal = Journal of Environmental Science and Health, Part C: Environmental Carcinogenesis & Ecotoxicology Reviews | year = 2005 | volume = C23 | issue = 2 | pages = 163–214 | doi = 10.1080/10590500500234988 | pmid = 16291527}}</ref> MX is found in chlorinated drinking water all over the world and is an environmental carcinogen that is known to cause several types of cancer in rats when present in large enough concentrations.<ref>{{cite journal | title = Oxidative stress and DNA damage induced by a drinking-water chlorination disinfection byproduct 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) in mice |author1=Yuan, Jing |author2=Liu, Hui |author3=Zhou, Li-Hong |author4=Zou, Ya-Lin |author5=Lu, Wen-Qing | journal = Mutation Research | year = 2006 | volume = 609 | issue = 2 | pages = 129–136 | pmid = 16952480 | doi = 10.1016/j.mrgentox.2006.05.011}}</ref> It is listed by the ] as a ] ] meaning it is "possibly carcinogenic to humans". Although the concentration of MX in drinking water is typically 100- to 1000-fold lower than other common byproducts of water chlorination such as ]s, MX might play a role in the increased cancer risks that have been associated with the consumption of chlorinated water because of its potency in inducing DNA damage.<ref>{{cite journal | title = Carcinogenicity of the chlorination disinfection by-product MX |author1=McDonald, Thomas A. |author2=Komulainen, Hannu | journal = Journal of Environmental Science and Health, Part C | year = 2005 | volume = C23 | issue = 2 | pages = 163–214 | doi = 10.1080/10590500500234988 | pmid = 16291527}}</ref>


==References== ==References==
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==External links== ==External links==
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Latest revision as of 03:39, 24 June 2020

Mutagen X
Skeletal formula of mutagen X
Space-filling model of the mutagen X molecule
Names
IUPAC name 3-Chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one
Other names Mutagen X
MX
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
EC Number
  • 253-575-7
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H3Cl3O3/c6-2-1(3(7)8)4(9)11-5(2)10/h3-4,9HKey: WNTRMRXAGJOLCU-UHFFFAOYSA-N
  • InChI=1/C5H3Cl3O3/c6-2-1(3(7)8)4(9)11-5(2)10/h3-4,9HKey: WNTRMRXAGJOLCU-UHFFFAOYAU
SMILES
  • O=C1OC(O)C(C(Cl)Cl)=C1Cl
Properties
Chemical formula C5H3Cl3O3
Molar mass 217.43 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Mutagen X (MX), or 3-chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one, is a byproduct of the disinfection of water by chlorination. MX is produced by reaction of chlorine with natural humic acids.

MX is found in chlorinated drinking water all over the world and is an environmental carcinogen that is known to cause several types of cancer in rats when present in large enough concentrations. It is listed by the International Agency for Research on Cancer as a group 2B carcinogen meaning it is "possibly carcinogenic to humans". Although the concentration of MX in drinking water is typically 100- to 1000-fold lower than other common byproducts of water chlorination such as trihalomethanes, MX might play a role in the increased cancer risks that have been associated with the consumption of chlorinated water because of its potency in inducing DNA damage.

References

  1. Yuan, Jing; Liu, Hui; Zhou, Li-Hong; Zou, Ya-Lin; Lu, Wen-Qing (2006). "Oxidative stress and DNA damage induced by a drinking-water chlorination disinfection byproduct 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) in mice". Mutation Research. 609 (2): 129–136. doi:10.1016/j.mrgentox.2006.05.011. PMID 16952480.
  2. McDonald, Thomas A.; Komulainen, Hannu (2005). "Carcinogenicity of the chlorination disinfection by-product MX". Journal of Environmental Science and Health, Part C. C23 (2): 163–214. doi:10.1080/10590500500234988. PMID 16291527.

External links

Categories: