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Methylchloroisothiazolinone

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Methylchloroisothiazolinone
Methylchloroisothiazolinone
Names
IUPAC name 5-Chlor-2-methyl-4-isothiazolin-3-one
Other names Chloromethylisothiazolinone; Chloromethylisothiazolone; Methylchloroisothiazolinone; Methylchloroisothiazolone; CMI; CMIT; MCI; MCIT
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.043.167 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3Key: DHNRXBZYEKSXIM-UHFFFAOYSA-N
  • InChI=1/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3Key: DHNRXBZYEKSXIM-UHFFFAOYAV
SMILES
  • ClC=1SN(C(=O)C=1)C
Properties
Chemical formula C4H4ClNOS
Molar mass 149.59 g·mol
Appearance colorless liquid
Density 1.02 g/cm³, liquid
Solubility in water miscible with
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Methylchloroisothiazolinone (5-chloro-2-methyl-4-isothiazolin-3-one) is a preservative with antibacterial and antifungal effects within the group of isothiazolinones. It is effective against gram-positive and gram-negative bacteria, yeast, and fungi.

Methylchloroisothiazolinone is found in many water-based personal care products and cosmetics. 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.

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

Safety

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.

The International Agency for Research on Cancer (IARC), does not currently list methylchloroisothiazolinone as a known, probable, or possible human carcinogen, nor have in vivo tests found evidence of carcinogenic activity. Methylchloroisothiazolinone is an allergen 2-3% of individuals. 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.

References

  1. Reinhard et al.: "Preservation of products with MCI/MI in Switzerland". Contact Dermatitis. 2001 Nov;45(5):257-64. PMID 11722483
  2. Knudsen BB, Menne T: "Kathon CG--a new contact sensitizing preservative". Ugeskr Laeger. 1990 Mar 5;152(10):656-7. PMID 2321281
  3. "International Agency for Research on Cancer". IARC (updated November 2007). Retrieved 7 January 2008.
  4. Zoller L, Bergman R, Weltfriend S. (2006). "Preservatives sensitivity in Israel: a 10-year overview (1995-2004)". Contact Dermatitis. 55 (4): 227–9. PMID 16958921.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. 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.

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