Methylchloroisothiazolinone: Difference between revisions

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| ImageSize1 = 160
| ImageSize1 = 160
| ImageAlt1 = Space-filling model of the methylchloroisothiazolinone molecule
| ImageAlt1 = Space-filling model of the methylchloroisothiazolinone molecule
| IUPACName = 5-Chloro-2-methyl-1,2-thiazol-3(2''H'')-one
| PIN = 5-Chloro-2-methyl-1,2-thiazol-3(2''H'')-one
| OtherNames = 5-Chloro-2-methylisothiazol-3(2''H'')-one<br />5-Chloro-2-methyl-4-isothiazolin-3-one<br />Chloromethylisothiazolinone<br />Chloromethylisothiazolone<br />Methylchloroisothiazolinone<br />Methylchloroisothiazolone<br />CMI<br />CMIT<br />MCI<br />MCIT
| OtherNames = 5-Chloro-2-methylisothiazol-3(2''H'')-one<br />5-Chloro-2-methyl-4-isothiazolin-3-one<br />Chloromethylisothiazolinone<br />Chloromethylisothiazolone<br />Methylchloroisothiazolinone<br />Methylchloroisothiazolone<br />CMI<br />CMIT<br />MCI<br />MCIT<br />CIT
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
Line 20: Line 20:
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DEL7T5QRPN
| UNII = DEL7T5QRPN
| Beilstein = 1210149
| EINECS = 247-500-7
| DrugBank = DB14197
| InChI = 1/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3
| InChI = 1/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3
| InChIKey = DHNRXBZYEKSXIM-UHFFFAOYAV
| InChIKey = DHNRXBZYEKSXIM-UHFFFAOYAV
Line 32: Line 35:
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| C=4|H=4|Cl=1|N=1|O=1|S=1
| C=4|H=4|Cl=1|N=1|O=1|S=1
| Appearance = Colorless liquid
| Appearance = white solid
| Density = 1.02 g/cm³
| Density = 1.02 g/cm<sup>3</sup>
| Solubility = Miscible
| Solubility = Miscible
| MeltingPt =
| MeltingPtC = 52
| BoilingPt =
| BoilingPt =
| pKa =
| pKa =
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| Section7 = {{Chembox Hazards
| Section7 = {{Chembox Hazards
| MainHazards =
| MainHazards =
| RPhrases = {{R23/24/25}} {{R34}} {{R43}} {{R50/53}}
| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS09}}
| GHSSignalWord = Danger
| SPhrases = {{(S2)}} {{S26}} {{S28}} {{S36/37/39}} {{S45}} {{S60}} {{S61}}
| HPhrases = {{H-phrases|300|301|310|311|314|317|330|331|335|410}}
| PPhrases = {{P-phrases|260|261|262|264|270|271|272|273|280|284|301+310|301+330+331|302+350|302+352|303+361+353|304+340|305+351+338|310|311|312|320|321|322|330|333+313|361|363|391|403+233|405|501}}
}}
}}
}}
}}


'''Methylchloroisothiazolinone''', also referred to as '''MCI''', is the [[organic compound]] with the formula S(C<sub>2</sub>HCl)C(O)N(CH<sub>3</sub>). It is a white solid that melts near room temperature. The compound is an [[isothiazolinone]], a class of [[heterocycle]]s used as [[biocide]]s. These compounds have an active sulphur moiety that is able to oxidize thiol-containing residues, thereby effectively killing most aerobic and anaerobic bacteria. MCI is often used in combination with [[methylisothiazolinone]], a mixture known as Kathon. The isothiazolinones have attracted attention because they can cause [[contact dermatitis]].<ref name=rev>{{cite journal |doi=10.3390/molecules25040991|title=Isothiazolinone Biocides: Chemistry, Biological, and Toxicity Profiles|year=2020|last1=Silva|first1=Vânia|last2=Silva|first2=Cátia|last3=Soares|first3=Pedro|last4=Garrido|first4=E. Manuela|last5=Borges|first5=Fernanda|last6=Garrido|first6=Jorge|journal=Molecules|volume=25|issue=4|page=991|pmid=32102175|pmc=7070760|doi-access=free}}</ref><ref name=Reinhard>{{cite journal | author = Reinhard| title = Preservation of products with MCI/MI in Switzerland | journal = Contact Dermatitis | year = 2001 | volume = 45 | issue = 5 | pages = 257–264 | pmid = 11722483 | doi=10.1034/j.1600-0536.2001.450501.x| s2cid = 21296570 |display-authors=etal}}</ref><ref name=Knudsen>{{cite journal | author = Knudsen BB, Menne T | title = Kathon CG--a new contact sensitizing preservative | journal = Ugeskrift for Lægerer | year = 1990 | volume = 152 | issue = 10 | pages = 656–657 | pmid = 2321281}}</ref> Methylchloroisothiazolinone is effective against [[Gram-positive bacteria|gram-positive]] and [[gram-negative bacteria]], [[yeast]], and [[fungi]].
'''Methylchloroisothiazolinone''' (5-chloro-2-methyl-4-isothiazolin-3-one), also referred to as MCI, is a [[preservative]] with antibacterial and antifungal effects within the group of [[isothiazolinone]]s. It is effective against [[Gram-positive bacteria|gram-positive]] and [[Gram-negative bacteria|gram-negative]] [[bacteria]], [[yeast]], and [[fungi]].


== Application ==
Methylchloroisothiazolinone is found in many water-based personal care products and cosmetics.<ref>{{cite journal | author = Reinhard| title = Preservation of products with MCI/MI in Switzerland | journal = Contact Dermatitis | year = 2001 | volume = 45 | issue = 5 | pages = 257–264 | pmid = 11722483 | doi=10.1034/j.1600-0536.2001.450501.x|display-authors=etal}}</ref> Methylchloroisothiazolinone was first used in cosmetics in the 1970s. It is also used in glue production, detergents, paints, fuels, and other industrial processes. Methylchloroisothiazolinone is known by the registered tradename Kathon CG when used in combination with [[methylisothiazolinone]].<ref>{{cite journal | author = Knudsen BB, Menne T | title = Kathon CG--a new contact sensitizing preservative | journal = Ugeskrift for Lægerer | year = 1990 | volume = 152 | issue = 10 | pages = 656–657 | pmid = 2321281}}</ref>
Methylchloroisothiazolinone is found in many water-based personal care products and cosmetics.<ref name=Reinhard/> Methylchloroisothiazolinone was first used in cosmetics in the 1970s. It is also used in glue production, detergents, paints, fuels, and other industrial processes. Methylchloroisothiazolinone is known by the registered tradename ''Kathon'' CG when used in combination with [[methylisothiazolinone]].<ref name=Knudsen/>


Methylchloroisothiazolinone may be used in combination with other preservatives including [[ethylparaben]], [[benzalkonium chloride]], or [[2-bromo-2-nitropropane-1,3-diol]].
Methylchloroisothiazolinone may be used in combination with other preservatives including [[ethylparaben]], [[benzalkonium chloride]], [[bronopol]] and [[phenoxyethanol]].


==Safety==
== Hazards ==
Methylchloroisothiazolinone can cause allergic reactions in some people.<ref name=Pirmez>{{cite journal | doi = 10.1111/bjd.13986| pmid = 26130214| title = Photoaggravated contact dermatitis to Kathon CG (methylchloroisothiazolinone/Methylisothiazolinone): A novel pattern of involvement in a growing epidemic?| journal = British Journal of Dermatology| volume = 173| issue = 5| pages = 1343–1344| year = 2015| last1 = Pirmez| first1 = R.| last2 = Fernandes| first2 = A.L.C.| last3 = Melo| first3 = M.G.M.| s2cid = 37257050}}</ref> The first publication of the preservative as a contact allergen was in 1988.<ref name="deGroot">{{Cite journal| last1 = De Groot | first1 = A. C.| last2 = Weyland | first2 = J. W.| title = Kathon CG: A review| journal = Journal of the American Academy of Dermatology| volume = 18| issue = 2 Pt 1| pages = 350–358| year = 1988| pmid = 3279090| doi=10.1016/s0190-9622(88)70051-1 }}</ref> Cases of photoaggravated allergic contact dermatitis, i.e. worsening of skin lesions after sun exposure, have also been reported.<ref name=Pirmez/>
In pure form or in high concentrations, methylchloroisothiazolinone is a skin and membrane irritant and causes chemical burns. In the United States, accepted concentrations are 15 ppm in rinse-offs and 8 ppm in other cosmetics.{{Citation needed|date=July 2007}} In Canada, the accepted concentrations are 15 ppm and 7.5 ppm respectively.<ref>{{cite web|url=http://www.hc-sc.gc.ca/cps-spc/cosmet-person/hot-list-critique/hotlist-liste-eng.php|title=Cosmetic Ingredient Hotlist: Prohibited and Restricted Ingredients|access-date=24 February 2015|website=Health Canada}}</ref> The Canadian levels are also reflected in a paper published in the International Journal of Toxicology.<ref>{{cite web|url=http://ijt.sagepub.com/content/11/1/75.abstract|title=6 Final Report on the Safety Assessment of Methylisothiazolinone and Methylchloroisothiazolinone|access-date=24 February 2015|website=sagepub.com|publisher=International Journal of Toxicology|doi=10.3109/10915819209141993|date=January 1992|pages=75–128}}</ref>


In pure form or in high concentrations, methylchloroisothiazolinone is a skin and membrane irritant and causes chemical burns. In the United States, maximum authorized concentrations are 15 ppm in rinse-offs (of a mixture in the ratio 3:1 of 5-chloro-2-methylisothiazol 3(2H)-one and 2-methylisothiazol-3 (2H)-one).<ref>{{Cite web|title=Annex VI release - 26 November 2017 - 201703|url=https://ww2.fda.gov.ph/attachments/article/15926/Annex%20VI%20release%20-%2026%20November%202017%20-%20201703.pdf|website=U.S. Food and Drug Administration}}</ref> In Canada, methylchloroisothiazolinone may only be used in rinse-off products in combination with methylisothiazolinone, the total concentration of the combination may not exceed 15 ppm.<ref>{{cite web|url=http://www.hc-sc.gc.ca/cps-spc/cosmet-person/hot-list-critique/hotlist-liste-eng.php|title=Cosmetic Ingredient Hotlist: Prohibited and Restricted Ingredients|access-date=15 February 2020|website=Health Canada|date=2004-06-18}}</ref>
The [[International Agency for Research on Cancer]] (IARC), does not currently list methylchloroisothiazolinone as a known, probable, or possible human [[carcinogen]],<ref name="IARC">{{cite web|url=http://monographs.iarc.fr/ENG/Classification/index.php|title=International Agency for Research on Cancer|work=IARC (updated November 2007)|accessdate=7 January 2008}}</ref> nor have ''[[in vivo]]'' tests found evidence of carcinogenic activity.


⚫
== References ==
===Allergic contact dermatitis===
{{medref|section|date=August 2013}}
Methylchloroisothiazolinone is an allergen and can cause severe skin reactions in some people.<ref name="onlinelibrary.wiley.com">Pirmez R, Fernandes ALC, Melo MGM. Photoaggravated contact dermatitis to Kathon CG (methylchloroisothiazolinone/methylisothiazolinone): a novel pattern of involvement in a growing epidemic? Br J Dermatol. 2015 Jun 30. doi: 10.1111/bjd.13986. [Epub ahead of print] http://onlinelibrary.wiley.com/doi/10.1111/</ref> Since 2013 the use of the product particularly in cosmetics has received increased media coverage in the UK. Some cosmetics with the MI in have been investigated by the [[BBC Watchdog programme]].<ref>http://www.bbc.co.uk/programmes/articles/5ZPXlnyFQlfsdWjQFC9kx2B/johnson-johnson-reformulate-suncream-recipe-after-watchdog-investigation</ref> The first publication of the preservative as a contact allergen was in 1988.<ref name="deGroot">{{Cite journal
| last1 = De Groot | first1 = A. C.
| last2 = Weyland | first2 = J. W.
| title = Kathon CG: A review
| journal = Journal of the American Academy of Dermatology
| volume = 18
| issue = 2 Pt 1
| pages = 350–358
| year = 1988
| pmid = 3279090
| doi=10.1016/s0190-9622(88)70051-1
}}</ref> A common indication of an allergic reaction is [[eczema]]-like symptoms including redness and itching, and upon longer exposure also burning sensations and blisters on the part of the skin that is exposed to the allergen.{{medcn|date=May 2014}} Cases of photoaggravated allergic contact dermatitis, i.e. worsening of skin lesions after sun exposure, have also been reported.<ref name="onlinelibrary.wiley.com"/> Continued exposure can lead to high sensitization which will be triggered each time the individual comes in contact with the allergen due to the memory [[T-cells]] that will remain in the local skin area.{{medcn|date=May 2014}}

⚫
==References==
{{Reflist}}
{{Reflist}}


==External links==
== External links ==
* [https://www.biobor.com/wp-content/uploads/2021/03/CMIT-MIT-Isothiazolone-Biocide-Assessment.pdf CMIT/MIT Assessment]
* {{HPD|197}}
* {{CPID|id=1935|name=Methylchloroisothiazoline}}
⚫
{{Use dmy dates|date=December 2010}}
* [https://www.ncbi.nlm.nih.gov/pubmed/?term=methylchloroisothiazolinone methylchloroisothiazolinone at the National Library of Medicine]
* [https://www.ncbi.nlm.nih.gov/pubmed/?term=methylchloroisothiazolinone Methylchloroisothiazolinone at the National Library of Medicine]


⚫
{{Use dmy dates|date=February 2021}}
[[Category:Preservatives]]
[[Category:Preservatives]]
[[Category:Isothiazolidinones]]
[[Category:Isothiazolidinones]]

Latest revision as of 00:36, 20 November 2023

Methylchloroisothiazolinone
Skeletal formula of methylchloroisothiazolinone
Space-filling model of the methylchloroisothiazolinone molecule
Names
Preferred IUPAC name
5-Chloro-2-methyl-1,2-thiazol-3(2H)-one
Other names
5-Chloro-2-methylisothiazol-3(2H)-one
5-Chloro-2-methyl-4-isothiazolin-3-one
Chloromethylisothiazolinone
Chloromethylisothiazolone
Methylchloroisothiazolinone
Methylchloroisothiazolone
CMI
CMIT
MCI
MCIT
CIT
Identifiers
3D model (JSmol)
1210149
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.043.167 Edit this at Wikidata
EC Number
  • 247-500-7
UNII
  • InChI=1S/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3 checkY
    Key: DHNRXBZYEKSXIM-UHFFFAOYSA-N checkY
  • InChI=1/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3
    Key: DHNRXBZYEKSXIM-UHFFFAOYAV
  • ClC=1SN(C(=O)C=1)C
Properties
C4H4ClNOS
Molar mass 149.59 g·mol−1
Appearance white solid
Density 1.02 g/cm3
Melting point 52 °C (126 °F; 325 K)
Miscible
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H300, H301, H310, H311, H314, H317, H330, H331, H335, H410
P260, P261, P262, P264, P270, P271, P272, P273, P280, P284, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P320, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Methylchloroisothiazolinone, also referred to as MCI, is the organic compound with the formula S(C2HCl)C(O)N(CH3). It is a white solid that melts near room temperature. The compound is an isothiazolinone, a class of heterocycles used as biocides. These compounds have an active sulphur moiety that is able to oxidize thiol-containing residues, thereby effectively killing most aerobic and anaerobic bacteria. MCI is often used in combination with methylisothiazolinone, a mixture known as Kathon. The isothiazolinones have attracted attention because they can cause contact dermatitis.[1][2][3] Methylchloroisothiazolinone is effective against gram-positive and gram-negative bacteria, yeast, and fungi.

Application[edit]

Methylchloroisothiazolinone is found in many water-based personal care products and cosmetics.[2] Methylchloroisothiazolinone was first used in cosmetics in the 1970s. It is also used in glue production, detergents, paints, fuels, and other industrial processes. Methylchloroisothiazolinone is known by the registered tradename Kathon CG when used in combination with methylisothiazolinone.[3]

Methylchloroisothiazolinone may be used in combination with other preservatives including ethylparaben, benzalkonium chloride, bronopol and phenoxyethanol.

Hazards[edit]

Methylchloroisothiazolinone can cause allergic reactions in some people.[4] The first publication of the preservative as a contact allergen was in 1988.[5] Cases of photoaggravated allergic contact dermatitis, i.e. worsening of skin lesions after sun exposure, have also been reported.[4]

In pure form or in high concentrations, methylchloroisothiazolinone is a skin and membrane irritant and causes chemical burns. In the United States, maximum authorized concentrations are 15 ppm in rinse-offs (of a mixture in the ratio 3:1 of 5-chloro-2-methylisothiazol 3(2H)-one and 2-methylisothiazol-3 (2H)-one).[6] In Canada, methylchloroisothiazolinone may only be used in rinse-off products in combination with methylisothiazolinone, the total concentration of the combination may not exceed 15 ppm.[7]

References[edit]

  1. ^ Silva, Vânia; Silva, Cátia; Soares, Pedro; Garrido, E. Manuela; Borges, Fernanda; Garrido, Jorge (2020). "Isothiazolinone Biocides: Chemistry, Biological, and Toxicity Profiles". Molecules. 25 (4): 991. doi:10.3390/molecules25040991. PMC 7070760. PMID 32102175.
  2. ^ a b Reinhard; et al. (2001). "Preservation of products with MCI/MI in Switzerland". Contact Dermatitis. 45 (5): 257–264. doi:10.1034/j.1600-0536.2001.450501.x. PMID 11722483. S2CID 21296570.
  3. ^ a b Knudsen BB, Menne T (1990). "Kathon CG--a new contact sensitizing preservative". Ugeskrift for Lægerer. 152 (10): 656–657. PMID 2321281.
  4. ^ a b Pirmez, R.; Fernandes, A.L.C.; Melo, M.G.M. (2015). "Photoaggravated contact dermatitis to Kathon CG (methylchloroisothiazolinone/Methylisothiazolinone): A novel pattern of involvement in a growing epidemic?". British Journal of Dermatology. 173 (5): 1343–1344. doi:10.1111/bjd.13986. PMID 26130214. S2CID 37257050.
  5. ^ De Groot, A. C.; Weyland, J. W. (1988). "Kathon CG: A review". Journal of the American Academy of Dermatology. 18 (2 Pt 1): 350–358. doi:10.1016/s0190-9622(88)70051-1. PMID 3279090.
  6. ^ "Annex VI release - 26 November 2017 - 201703" (PDF). U.S. Food and Drug Administration.
  7. ^ "Cosmetic Ingredient Hotlist: Prohibited and Restricted Ingredients". Health Canada. 18 June 2004. Retrieved 15 February 2020.

External links[edit]

Retrieved from "https://en.wikipedia.org/w/index.php?title=Methylchloroisothiazolinone&oldid=1185954167"