:Mutagen X

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 433354158

| Name = Mutagen X

| ImageFile = MX structure.png

| ImageSize = 150

| ImageAlt = Skeletal formula of mutagen X

| ImageFile1 = Mutagen-X-3D-spacefill.png

| ImageSize1 = 150

| ImageAlt1 = Space-filling model of the mutagen X molecule

| IUPACName = 3-Chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one

| OtherNames = Mutagen X
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 = C19205

| 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

| Formula = C₅H₃Cl₃O₃

| MolarMass = 217.43 g/mol

| Density =

| MeltingPt =

}}

}}

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.{{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}} It is listed by the International Agency for Research on Cancer as a group 2B carcinogen meaning it is "possibly carcinogenic to humans", a category it shares with carpentry and pickled vegetables.{{cite web |title=Agents classified by the IARC Monographs, Volumes 1–137 |publisher=The World Health Organisation |url=https://monographs.iarc.who.int/list-of-classifications/ |access-date=13 January 2025 }} 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.{{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}}