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Revision as of 06:57, 10 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit		Latest revision as of 08:35, 4 January 2025 edit undoNardog (talk | contribs)Edit filter helpers, Autopatrolled, Extended confirmed users, New page reviewers, Pending changes reviewers, Rollbackers, Template editors82,584 edits unsourced and inaccurate
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	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 400834945		| verifiedrevid = 445572264
	| Name = Methylchloroisothiazolinone		| Name = Methylchloroisothiazolinone
	| ImageFile = Methylchloroisothiazolinone structure.svg		| ImageFile = Methylchloroisothiazolinone structure.svg
	| ImageSize = 150px		| ImageSize = 160
			| ImageAlt = Skeletal formula of methylchloroisothiazolinone
	| ImageName = Methylchloroisothiazolinone		| ImageFile1 = Methylchloroisothiazolinone-3D-spacefill.png
⚫	| IUPACName = 5-Chlor-2-methyl-4-isothiazolin-3-one
			| ImageSize1 = 160
⚫	| OtherNames = Chloromethylisothiazolinone; Chloromethylisothiazolone; Methylchloroisothiazolinone; Methylchloroisothiazolone; CMI; CMIT; MCI; MCIT
			| ImageAlt1 = Space-filling model of the methylchloroisothiazolinone molecule
		⚫	| 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<br />CIT
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 53621		| ChEBI = 53621
	| SMILES = ClC=1SN(C(=O)C=1)C		| SMILES = ClC=1SN(C(=O)C=1)C
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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	| 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
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 26172-55-4		| CASNo = 26172-55-4
	| RTECS =		| RTECS =
	}}		}}
	| 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, liquid		| Density = 1.02 g/cm<sup>3</sup>
	| Solubility = miscible with		| Solubility = Miscible
	| MeltingPt =		| MeltingPtC = 52
	| BoilingPt =		| BoilingPt =
	| pKa =		| pKa =
	| pKb =		| pKb =
	| Viscosity =		| Viscosity =
	}}		}}
	| 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 ] 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 ], a class of ]s used as ]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 ], a mixture known as Kathon. The isothiazolinones have attracted attention because they can cause ].<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 ] and ], ], and ].
	'''Methylchloroisothiazolinone''' (5-chloro-2-methyl-4-isothiazolin-3-one) is a ] with antibacterial and antifungal effects within the group of ]s. It is effective against ] and ] ], ], and ].
			== Application ==
	Methylchloroisothiazolinone is found in many water-based personal care products and cosmetics.<ref>Reinhard et al.: "Preservation of products with MCI/MI in Switzerland". ''Contact Dermatitis.'' 2001 Nov;45(5):257-64. PMID 11722483</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 ].<ref>Knudsen BB, Menne T: "Kathon CG--a new contact sensitizing preservative". ''Ugeskr Laeger.'' 1990 Mar 5;152(10):656-7. 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 ].<ref name=Knudsen/>
	Methylchloroisothiazolinone may be used in combination with other preservatives including ], ], or ].		Methylchloroisothiazolinone may be used in combination with other preservatives including ], ], ] and ].
	==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 can be a skin and membrane irritant or cause chemical burns. It was largely removed from most cosmetic products except for those with only short duration skin contact such as rinse-offs. Its inclusion in certain forms makes it more acceptable to sensitive users, so it can be found in cosmetic creams and lotions which require skin contact. In the United States, accepted concentrations are 15 ppm in rinse-offs and 8 ppm in other cosmetics.{{Citation needed|date=July 2007}}
			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>
	] (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.{{Citation needed|date=July 2007}} Methylchloroisothiazolinone is an allergen 2-3% of individuals.<ref name="ZollerL">{{cite journal | author = Zoller L, Bergman R, Weltfriend S. | title = Preservatives sensitivity in Israel: a 10-year overview (1995-2004) | journal = Contact Dermatitis | year = 2006 | volume = 55 | issue = 4 | pages = 227–9 | pmid = 16958921}}</ref><ref>Zug KA, Warshaw EM, Fowler JF Jr, Maibach HI, Belsito DL, Pratt MD, Sasseville D, Storrs FJ, Taylor JS, Mathias CG, Deleo VA, Rietschel RL, Marks J. Dermatitis. Patch-test results of the North American Contact Dermatitis Group 2005-2006. 2009 May-Jun;20(3):149-60.</ref> A common indication of an allergic reaction is eczematous (rashy) symptoms such as redness and itching on surfaces exposed to the allergen. These symptoms will disappear several weeks after exposure is ceased. Common points of exposure in household items are shampoos, hair conditioners, soaps and pre-moistened toilet/bath wipes.
			Methylisothiazolinone is considered safe in the allowed amount in rinse-off products (0.1%) and safe in leave-in products when formulated to be non-sensitizing.<ref>{{Cite journal |last=Burnett |first=Christina L. |last2=Bergfeld |first2=Wilma F. |last3=Belsito |first3=Donald V. |last4=Cohen |first4=David |last5=Klaassen |first5=Curtis D. |last6=Liebler |first6=Daniel C. |last7=Marks |first7=James G. |last8=Peterson |first8=Lisa A. |last9=Shank |first9=Ronald C. |last10=Slaga |first10=Thomas J. |last11=Snyder |first11=Paul W. |last12=Heldreth |first12=Bart |date=2021 |title=Amended Safety Assessment of Methylisothiazolinone as Used in Cosmetics |url=https://pubmed.ncbi.nlm.nih.gov/34259065/#:~:text=The%20Panel%20reviewed%20relevant%20animal%20and%20human%20data,on%20a%20quantitative%20risk%20assessment%20or%20similar%20methodology. |journal=International Journal of Toxicology |volume=40 |issue=1_suppl |pages=5S–19S |doi=10.1177/10915818211015795 |issn=1092-874X |pmid=34259065}}</ref>
⚫	==References==
	<references/>
			An overdose of Kathon by aircraft maintenance personnel, using 38 times the correct amount, resulted in damage to both engines of a ] aircraft in February 2020. After losing both engines in succession, the ] made an emergency landing at ] Airport.<ref></ref> The maintenance procedures specified the Kathon to be diluted to 100 ] by volume, but with the aircraft maintenance technician being unfamiliar with the term "PPM" and the term not being defined in the aircraft maintenance manuals, the technician instead used an online calculator to convert PPM to percentages, misinterpreted the answer, and added 30 kg of Kathon to each wing tank, which was over 38 times the required amount. Over the course of the next day, the Kathon progressively caused more and more damage to the engines, finally resulting in an emergency landing.<ref></ref>
⚫	==External links==
	* {{HPD|197}}
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		⚫	== References ==
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		⚫	== External links ==
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			* {{CPID|id=1935|name=Methylchloroisothiazoline}}
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		⚫	{{Use dmy dates|date=February 2021}}
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