Methylchloroisothiazolinone

Last updated
Methylchloroisothiazolinone
Methylchloroisothiazolinone structure.svg
Methylchloroisothiazolinone-3D-spacefill.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 247-500-7
PubChem CID
UNII
  • InChI=1S/C4H4ClNOS/c1-6-4(7)2-3(5)8-6/h2H,1H3 Yes check.svgY
    Key: DHNRXBZYEKSXIM-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancewhite solid
Density 1.02 g/cm3
Melting point 52 °C (126 °F; 325 K)
Miscible
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Application

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

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]

Related Research Articles

<span class="mw-page-title-main">Methylisothiazolinone</span> Chemical compound

Methylisothiazolinone, MIT, or MI, is the organic compound with the formula S(CH)2C(O)NCH3. It is a white solid. Isothiazolinones, a class of heterocycles, are used as biocides in numerous personal care products and other industrial applications. MIT and related compounds have attracted much attention for their allergenic properties, e.g. contact dermatitis.

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<span class="mw-page-title-main">Allergic contact dermatitis</span> Medical condition

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References

  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. 1 2 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. 1 2 Knudsen BB, Menne T (1990). "Kathon CG--a new contact sensitizing preservative". Ugeskrift for Lægerer. 152 (10): 656–657. PMID   2321281.
  4. 1 2 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.

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