Methylisothiazolinone
Methylisothiazolinone
Preferred IUPAC name= 2-Methyl-1,2-thiazol-3(2H)-one = MIT = MI = 2-methyl-2H-isothiazol-3-one
Other names
2-Methylisothiazol-3(2H)-one
2-Methyl-4-isothiazolin-3-one
2-methyl-2H-isothiazol-3-one
MIT
MI
Identifiers
CAS Number: 2682-20-4
EC / List no.: 220-239-6
Mol. formula: C4H5NOS
MIT, MI
Methylisothiazolinone is used to control slime-forming bacteria, fungi, and algae in pulp/paper mills, cooling water systems, oil field operations, industrial process waters, and air washer systems and is incorporated into adhesives, coatings, fuels, metal working fluids, resin emulsions, paints, and various other speciality industrial products as a preservative.
Methylisothiazolinone is also used to control the growth of mold, mildew, and sapstain on wood products.
Formulations include soluble concentrated liquids and soluble concentrated solids.
Products containing methylisothiazolinone are added to systems and industrial products using manual pouring and metered pumping methods, dip tanks and sprayers
Methylisothiazolinone, MIT, or MI, is the organic compound with the formula S(CH)2C(O)NCH3.
Methylisothiazolinone (short for MIT or MI; sometimes erroneously called methylisothiazoline), is a powerful synthetic biocide and preservative within the group of isothiazolinones.
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.
Preparation
It is prepared by cyclization of cis-N-methyl-3-thiocyanoacrylamide.
MI is a clear, colourless liquid that is soluble in water. It enhances the safety and shelf-life of products by preventing the growth of bacteria and yeasts.
Without preservatives like MI, products could start to smell unpleasant, change colour or grow moulds which can produce toxins which are harmful to health.
Methylisothiazolinone (MI) is a preservative that’ super efficient against bacteria at surprisingly low concentrations. The problem with it though is that it can also sensitize and irritate the skin quite easily when it comes in leave-on formulas.
Methylisothiazolinone (MI), along with Kathon™ CG (methylchloroisothiazolinone/MI), are widely used preservatives to prevent bacterial overgrowth in aqueous solutions of various types of cosmetic, household, and industrial products.
Because of its high sensitising power and widespread use, MI is currently one of the most common causes of allergic contact dermatitis, both in our private lives and in the occupational field. As it was thought that MI had less sensitivity capacity, it started to be commercialised separately, and a new epidemic of sensitisation to these preservatives has been observed in recent years. MI should be included separately in the standard patch testing series. Also, the use of isothiazolinones should be revised, and legislative measures from the competent authorities should be implemented in order to resolve this problem.
Methylisothiazolinone is used as a biocide and preservative in cosmetics, paints, and glues; it is present in Kathon KG, MCI/MI, and Euxyl K100;
Methylisothiazolinone is used as an antimicrobial in cosmetics, hygiene products, paints, emulsions, cutting oils, paper coatings, and water storage and cooling units;
Methylisothiazolinone is used as a biocide in textile production
Used as a preservative in pesticide products
Used as a biocide in pulp/paper mills, industrial process and cooling water systems, oil field operations, and air cleaner systems, and as a preservative in adhesives, coatings, fuels, metalworking fluids, resin emulsions, paints, and wood products;
Methylisothiazolinone (MIT) is a preservative used in personal care products to stop fungus, bacteria and other microbes from growing in water solutions.
Methylisothiazolinone (MIT) helps maintain product quality and performance over time.
2-Methyl-4-isothiazolin-3-one hydrochloride is an isothiazolinone based biocide and preservative used in personal care products.
2-Methyl-4-isothiazolin-3-one is also used for controlling microbial growth in water-containing solution.
Applications
Main article: Isothiazolinone
Methylisothiazolinone is used for controlling microbial growth in water-containing solutions.
It is typically used in a formulation with 5-chloro-2-methyl-4-isothiazolin-3-one (CMIT), in a 3:1 mixture (CMIT:MIT) sold commercially as Kathon.
Kathon is supplied to manufacturers as a concentrated stock solution containing from 1.5–15% of CMIT/MIT.
Kathon also has been used to control slime in the manufacture of paper products that contact food.
In addition, this product serves as an antimicrobial agent in latex adhesives and in paper coatings that also contact food.
MIT is used to protect products from contamination by potentially pathogenic microbes (fungi and bacteria). Its use allows to ensure the product is safe for consumers.
Methylisothiazolinone is a synthetic chemical used in consumer products for its antimicrobial properties.
Methylisothiazolinone is most often applied to cleaning products as a synthetic preservative.
Methylisothiazolinone is used to extend a product’s shelf life and protect consumers against exposure to bacteria and mold by inhibiting the growth of those organisms.
Methylisothiazolinone can be found on product labels under the following names:
MI
MIT
2-methyl-4-isothiazoline-3-one
Neolone 950 preservative
OriStar MIT
Microcare MT
Applications
Methylisothiazolinone and other isothiazolinone-derived biocides are utilized for controlling microbial growth in water-containing solutions.
Two of the most widely used isothiazolinone biocides are 5-chloro-2-methyl-4-isothiazolin-3-one (chloromethylisothiazolinone or CMIT) and 2-methyl-4-isothiazolin-3-one (methylisothiazolinone or MIT), which are the active ingredients in a 3:1 mixture (CMIT:MIT) sold commercially as Kathon.
Biocidal applications range from industrial water storage tanks to cooling units, in processes as varied as mining, paper manufacturing, and energy production.
Methylisothiazolinone Chemical Properties, Uses, Production
Description
Methylisothiazolinone (also called 2-methyl-4-isothiazolin-3-one), is a powerful synthetic biocide and preservative within the group of isothiazolinones.
Methylisothiazolinone is used to control slime-forming bacteria, fungi, and algae in pulp/paper mills, cooling water systems, oil field operations, industrial process waters, and air washer systems. And it is incorporated into adhesives, coatings, fuels, metal working fluids, resin emulsions, paints, and various other specialty industrial products as a preservative.
It is also used to control the growth of mold, mildew, and sapstain on wood products.
It is generally recommended for use only in rinse-off and leave-on cosmetic products (maximum concentration of 100 ppm) as preservative such as shampoo, conditioner, hair color, body wash, lotion, sunscreen, mascara, shaving cream, baby lotion, baby shampoo, hairspray, makeup remover, liquid soaps, and detergents. Nevertheless, methylisothiazolinone is allergenic.
It is reported that methylisothiazolinone in rinse-off products causes allergic contact dermatitis.
Uses
Methylisothiazolinone, or MIT as it is sometimes known, is a preservative used in cosmetics and beauty products.
It is a powerful biocide, or “chemical substance capable of killing living organisms, usually in a selective way.
”Biocides are a general term that includes antimicrobial, germicide, antibiotic, and antifungal.
Ultimately, Methylisothiazolinone is used to prevent a wide variety of bacteria and fungi from growing in cosmetics and beauty products, most often in shampoo.
It is only approved for use in rinse-off formulas and at low concentrations.
Safety
Methylisothiazolinone (MIT) is a heterocyclic organic compound used as a preservative in cosmetics and personal care products in concentrations up to 0.01%.
MIT is a colorless, clear liquid with a mild odor that is completely soluble in water; mostly soluble in acetonitrile, methanol, and hexane; and slightly soluble in xylene.
Hazards
MIT is allergenic and cytotoxic, and this has led to some concern over its use.
A report released by the European Scientific Committee on Cosmetic Products and Non-food Products Intended for Consumers (SCCNFP) in 2003 also concluded that insufficient information was available to allow for an adequate risk assessment analysis of MIT.
Rising reports of consumer impact led to new research, including a report released in 2014 by the European Commission Scientific Committee on Consumer Safety which reported: “The dramatic rise in the rates of reported cases of contact allergy to MI, as detected by diagnostic patch tests, is unprecedented in Europe; there have been repeated warnings about the rise.
The increase is primarily caused by increasing consumer exposure to MI from cosmetic products; exposures to MI in household products, paints and in the occupational setting also need to be considered.
The delay in re-evaluation of the safety of MI in cosmetic products is of concern to the SCCS; it has adversely affected consumer safety.
Regulation
In 2014, the European Commission Scientific Committee on Consumer Safety further issued a voluntary ban on the MCI/MI mixture from leave-on products such as body creams.
The measure applied for products placed on the market after 16 July 2015.”
Shortly thereafter, Canada moved to adopt similar measures in its Cosmetic Ingredients Hotlist.
Based on the opinion of the Scientific Committee on Consumer Safety (SCCS) of 2013, Commission Regulation (EU) 2016/1198 of 22 July 2016 amending Annex V to Regulation (EC) No 1223/2009 of the European Parliament and of the Council on cosmetic products banned the use of methylisothiazolinone in leave-on products (skin creams and lotions) effective 12 February 2017 and limited it to 0.01% in rinse-off products (e.g. shampoo).
Effective 27 January 2018 (placing on the market), the maximum concentration in rinse-off products was reduced to 0.0015 %.
Methylisothiazolinone (MIT) and Methylchloroisothiazolinone (CMIT) are widely used preservatives found in liquid products
Both chemicals inhibit bacterial growth in cosmetic products on their own, but they are most commonly used as a mixture in products.
Translated names
2-Methyl-(2H)-isothiazol-3-on (de)
2-methyl-2H-isothiazol-3-on (MIT) (da)
2-Methyl-2H-isothiazol-3-on (MIT) (de)
2-methyl-2H-isothiazol-3-one (MIT) (mt)
2-methyl-2H-isothiazol-3-one (MIT) (no)
2-Methyl-2H-isothiazool-3-on (MIT) (nl)
2-methylisothiazol-3(2H)-on (cs)
2-methylisothiazol-3(2H)-on (da)
2-methylisothiazool-3(2H)-on (nl)
2-methyltetrahydroisothiazol-3(2H)-on (MIT) (cs)
2-Metil-2H-isotiazol-3-ona (MIT) (es)
2-Metil-2H-isotiazol-3-ona (MIT) (pt)
2-metil-2H-isotiazol-3-one (MIT) (it)
2-metil-2H-isotiazol-3-onă (MIT) (ro)
2-metil-2H-izotiazol-3-on (MIT) (hr)
2-metil-2H-izotiazol-3-on (MIT) (hu)
2-metil-2H-izotiazol-3-on (MIT) (sl)
2-metil-2H-izotiazol-3-onas (MIT) (lt)
2-Metil-2H-izotiazol-3-ons (MIT) (lv)
2-metilisotiazol-3(2H)-on (hu)
2-metilisotiazol-3(2H)-on (mt)
2-Metilisotiazol-3(2H)-ona (es)
2-metilisotiazol-3(2H)-ona (pt)
2-metilisotiazol-3(2H)-one (it)
2-metilizotiazol-3(2H)-on (hr)
2-metilizotiazol-3(2H)-on (sl)
2-metilizotiazol-3(2H)-onas (lt)
2-metilizotiazol-3(2H)-ons (lv)
2-metilizotiazol-3(2H)-onă (ro)
2-metyl-(2H)-izotiazol-3-ón (sk)
2-metyl-2H-isotiazol-3-on (MIT) (sv)
2-metyl-2H-izotiazol-3-ón (MIT) (sk)
2-metylisotiazol-3(2H)-on (sv)
2-metylo-2H-izotiazol-3-on (MIT) (pl)
2-metyloizotiazol-3(2H)-on (pl)
2-metyyli-2H-isotiatsol-3-oni (MIT) (fi)
2-metyyli-isotiatsol-3(2H)-oni (fi)
2-metüül-2H-isotiasool-3-oon (MIT) (et)
2-metüülisotiasool-3(2H)-oon (et)
2-méthyl-2H-isothiazole-3-one (MIT) (fr)
2-méthylisothiazol-3(2H)-one (fr)
2-Μεθυλ-2H-ισοδιαζολ-3-όνη (MIT) (el)
2-μεθυλισοθειαζολ-3(2H)-όνη (el)
2-метил-2H-изотиазол-3-он (MIT) (bg)
2-метилизотиазол-3(2H)-он (bg)
IUPAC names
2-Methyl-1,2-thiazol-3(2H)-one
2-methyl-1,2-thiazol-3(2H)-one
2-methyl-1,2-thiazol-3-one
2-methyl-1,2-thiazol-3-one hydrochloride
2-methyl-2,3-dihydro-1,2-thiazol-3-one
2-Methyl-2H-isothiazol-3-one
2-Methyl-3(2H)-isothiazolon
2-Methyl-3(2H)-isothiazolone
2-Methyl-3(2H)-isothiazolone
2-methyl-4- isothiazolin-3-one
2-Methyl-4-isothiazol-3-one
2-Methyl-4-isothiazolin-3-one
2-Methylisothiazol-3(2H)-one
2-methylisothiazol-3(2H)-one
2-Methylisothiazolin-3-one
3(2H) -Isothiazolone, 2-methyl-
3(2H)-Isothiazolone, 2-methyl-
Methylisothiazolinone
Trade names
2-Methyl-4-isothiazolin-3-one
2-Methyl-4-isothiazolin-3-one (MI); 50% aqueous solution
Syntomast
MIT 50 %
220-239-6 [EINECS]
2682-20-4 [RN]
2-Methyl-1,2-thiazol-3(2H)-on [German] [ACD/IUPAC Name]
2-Methyl-1,2-thiazol-3(2H)-one [ACD/IUPAC Name]
2-Méthyl-1,2-thiazol-3(2H)-one [French] [ACD/IUPAC Name]
2-methyl-4-isothiazolin-3-one
2-Methyl-4-isothiazoline-3-one
2-Methylisothiazol-3(2H)-one [ACD/IUPAC Name]
3(2H)-Isothiazolone, 2-methyl- [ACD/Index Name]
606203 [Beilstein]
methylisothiazolinone [Wiki]
MFCD01742315 [MDL number]
MI
MIT
N-Methylisothiazolone
NX8157080
T5SNVJ B1 [WLN]
2682-20-4 (free base)
2-Methyl 4-Isothiazoline 3-one
2-methyl-1,2-thiazol-3-one
2-methyl-2,3-dihydro-1,2-thiazol-3-one
2-Methyl-2H-isothiazol-3-one
2-methyl-3-isothiazolidinone
2-methyl-3-isothiazolone
2-Methyl-4-isothiazolin-3-one (MI)
2-Methyl-4-isothiazolin-3-one (MI), 50% aq. solution
2-Methyl-4-isothiazolin-3-one 100 µg/mL in Acetonitrile
2-methyl-4-isothiazolin-3-one(mit)
2-Methyl-4-isothiazoline-3-one, 50% aqueous solution
2-methylisothiazol-3-one
3(2H)-ISOTHIAZOLONE, METHYL-
4670-10-4 [RN]
50% aqueous solution
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:53620
Methylisothiazolinone|2-methyl-3(2H)-isothiazolone
NCGC00164391-01
N-Methyl-3-oxodihydroisothiazole
N-Methyl-3-oxodihydroisothiazole, 95%
甲基异噻唑啉酮 [Chinese]
MIT is used as a preservative in cleaning products such as carpet cleaners, dishwashing liquids, fabric softeners, floor polishes, general cleaners, and sprinkler liquids
This chemical functions as a biocide and preservative within the group of isothiazolinones and is widely used in cosmetics, shampoos, soaps and body care products, cooling fluids, etc.
Methylisothiazolinone is typically used in conjunction with methylchloroisothiazolinone.
This combination is sold under the trademark of Kathon CG.
Use of products using these chemicals can result in eczema-like allergic reactions on areas of product usage.
Ceasing product use will usually result in the reaction disappearing.
Further research may identify additional product or industrial usages of this chemical.
Methylisothiazolinone or MIT, sometimes erroneously called methylisothiazoline, is a powerful biocide and preservative within the group of isothiazolinones, used in shampoos and body care products. Though long considered safe for use in cosmetics, two recent in vitro studies have shown that MIT is neurotoxic, causing damage to rat brain cells in tissue culture. Long-term health and safety studies have been conducted on animals, and thus far there is no published evidence of nerve damage or neurological effects associated with MIT for consumers or workers.
• 1-(4-CHLOROPHENYL)-3-(3,4-DICHLOROPHENYL)UREA
• 2-METHYL-4-ISOTHIAZOLIN-3-ONE
• 2-METHYL-4-ISOTHIAZOLINE-3-ONE
• 2-METHYL-3(2H)-ISOTHIAZOLONE
• N-METHYL-3-OXODIHYDRO ISOTHIAZOLE
• 2-methyl-3(2h)-isothiazolon
• Isothiazolone,2-methyl-
• Methylisothiazolinone
• Skycide 100
• 2-methyl-2H-isothiazol-3-one
• 2-Methyl-4-isothiazolin-3-one (Discontinued, see M314985)
• 2-Methyl-4-iso
• Isothiazolone 14%
• 2-methyl-1,2-thiazol-3-one
• MIT, 100ppm
• Isothiazolone
• 2-Methylisothiazolin-3-one
• 2-METHYL-4-ISOTHIAZOLIN-3-ONE (MI)
• METHYLISOTHIAZOLINE
• KATHON CG
• METHYLISOTHIAZDINONE
• METHYLISOTHIAZOLIN
• 2-METHYLISOTHIAZOLIN-3(2H)-ONE
• 2-METHYLISOTHIAZOLINONE
• METHYLISOTHIAZOLONE
• 2-methyl-4-isothiazolin-3-one MIT
• 5-Chloro-2-methyl-4-isothiazolin-3-one/2-Methyl-4-isothiazolin (CMIT/MIT-14)
• 3(2H)-Isothiazolone, 2-methyl-
• 2-Methyl-3-isothiazolone(MIT)
• 2-METHYL-4-ISOTHIAZOLIN-3-ONE(MIT) 50% WATER SOLUTION
• MIT 50%
• 2-Methyl-4-isothiazolin (CMIT/MIT-14)
• 2- METHYL-4-ISOTHIAZOLINE-3-KETONE
• 2-METHYL-4-ISOTHIAZOLIN-3-ONE, 90+%
• 2-Methyl-2,3-dihydroisothiazol-3-one
• 2-Methyl-3-isothiazolone
• 2-Methylisothiazol-3-one
• Methyl-3(2H)-isothiazolone
• 3,4,4”-TRICHLOROCARBANILIDE(TCC)
• 2-Methyl-2H-isothiazole-3-one
• 2-Methylisothiazol-3(2H)-one
• 2-Methylisothiazole-3-one
• 2-Methyl-4-isothiazolin-3-one,2-Methyl-3(2H)-isothiazolone
• 2-Methyl-4-isothiazolin-3-on
• 2-Methyl-4-Isothiazolin-3-Ketone
• 2-Methyl-2,3-dihydro-1,2-thiazol-3-one
• 5-chloro- Methyl-4-thiazoline-3-ketone(MI)
• 2-Methyl-4-Isothiazolin-3-Ketone (MIT)
• Methylisothiazolinone(MIT)
• MIT-50/ Methylisothiazolinone
• MIT-10/2-methyl-4-ishothiazolin-3-one
• Different thiazole moiety
• Methyl isothiazalinone
• MIT-20
• 2-Methyl-4-isothiazolin-3-one, 50% aqueous solution
• Methylisothiazolinone (2-Methyl-4-isothiazolin-3-one)
• 2-Methyl-4-Isothiazolin-3-one ( MIT 50% ) / Isothiazolinones 50%
• Methylisothiazolinone