Methylisothiazolinone

Last updated
Methylisothiazolinone
Methylisothiazolinone.svg
Methylisothiazolinone-3D-spacefill.png
Names
Preferred IUPAC name
2-Methyl-1,2-thiazol-3(2H)-one
Other names
2-Methylisothiazol-3(2H)-one
2-Methyl-4-isothiazolin-3-one
Identifiers
3D model (JSmol)
AbbreviationsMIT, MI
606203
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.018.399 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 220-239-6
PubChem CID
UNII
  • InChI=1S/C4H5NOS/c1-5-4(6)2-3-7-5/h2-3H,1H3 Yes check.svgY
    Key: BEGLCMHJXHIJLR-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H5NOS/c1-5-4(6)2-3-7-5/h2-3H,1H3
  • O=C1/C=C\SN1C
Properties
C4H5NOS
Molar mass 115.1 g/mol
Appearancewhite solid
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Danger
H301, H311, H314, H317, H330, H410
P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, 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 ?)

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. [1]

Contents

Preparation

It is prepared by cyclization of cis-N-methyl-3-thiocyanoacrylamide: [2]

Applications

Methylisothiazolinone is used for controlling microbial growth in water-containing solutions. [3] 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 to 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. [4]

Hazards

MIT is allergenic and cytotoxic, and this has led to some concern over its use. [5] [6] 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. [7]

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." [8] The American Contact Dermatitis Society named methylisothiazolinone “contact allergen of the year” in 2013. [9] The North American Contact Dermatitis Group found that methylisothiazolinone caused 10.9% positive reactions, being the third most common contact allergen in patch test results which surveyed close to 5000 contact dermatitis patients. [10] Additionally, new research into cross reactivity of MIT-sensitized patients to variants benzisothiazolinone and octylisothiazolinone have found that reactions may occur if present in sufficient amounts. [11]

In the United States, the Environmental Protection Agency has a 1998 data sheet on methylisothiazolinone in their Pesticides section [12] which reads in part "Human Health Assessment: Toxicity: In studies using laboratory animals, methylisothiazolinone has been shown to be of moderate acute toxicity by the oral and inhalation routes. It is highly acutely toxic when applied dermally or to the eye and is considered to be corrosive."

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." [13] Shortly thereafter, Canada moved to adopt similar measures in its Cosmetic Ingredients Hotlist. [14]

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). [15] Effective 27 January 2018 (placing on the market), the maximum concentration in rinse-off products was reduced to 0.0015%. [16]

Related Research Articles

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

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. Methylchloroisothiazolinone is effective against gram-positive and gram-negative bacteria, yeast, and fungi.

<span class="mw-page-title-main">Cosmetics</span> Substances applied to the body to change appearance or fragrance

Cosmetics are constituted mixtures of chemical compounds derived from either natural sources, or synthetically created ones. Cosmetics have various purposes. Those designed for personal care and skin care can be used to cleanse or protect the body or skin. Cosmetics designed to enhance or alter one's appearance (makeup) can be used to conceal blemishes, enhance one's natural features, add color to a person's face, or change the appearance of the face entirely to resemble a different person, creature or object. Due to the harsh ingredients in makeup products, individuals with acne-prone skin are more likely to suffer from breakouts. Cosmetics can also be designed to add fragrance to the body.

A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a slightly different definition for biocides as "a diverse group of poisonous substances including preservatives, insecticides, disinfectants, and pesticides used for the control of organisms that are harmful to human or animal health or that cause damage to natural or manufactured products". When compared, the two definitions roughly imply the same, although the US EPA definition includes plant protection products and some veterinary medicines.

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

Oxybenzone or benzophenone-3 or BP-3 is an organic compound belonging to the class of aromatic ketones known as benzophenones. It is a pale-yellow solid that is readily soluble in most organic solvents. It is widely used in sunscreen formulations, plastics, toys, furniture finishes, and other products to limit UV degradation. In nature, oxybenzone can be found in various flowering plants. The compound was first synthesised in Germany by chemists König and Kostanecki in 1906.

<span class="mw-page-title-main">Triclosan</span> Antimicrobial agent

Triclosan is an antibacterial and antifungal agent present in some consumer products, including toothpaste, soaps, detergents, toys, and surgical cleaning treatments. It is similar in its uses and mechanism of action to triclocarban. Its efficacy as an antimicrobial agent, the risk of antimicrobial resistance, and its possible role in disrupted hormonal development remains controversial. Additional research seeks to understand its potential effects on organisms and environmental health.

<span class="mw-page-title-main">Paraben</span> Class of chemical compounds; esters of parahydroxybenzoic acid

Parabens are chemicals that are commonly used as preservatives in cosmetic and pharmaceutical products. Chemically, they are a series of parahydroxybenzoates or esters of parahydroxybenzoic acid. Research is being conducted to evaluate the potential health implications of paraben usage.

Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.

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

Bronopol is an organic compound that is used as an antimicrobial. It is a white solid although commercial samples appear yellow.

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

Benzisothiazolinone (BIT) is an organic compound with the formula C6H4SN(H)CO. A white solid, it is structurally related to isothiazole, and is part of a class of molecules called isothiazolinones. BIT is widely used as a preservative and antimicrobial.

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

Isothiazolinone (sometimes isothiazolone) is an organic compound with the formula (CH)2SN(H)CO. A white solid, it is structurally related to isothiazole. Isothiazolone itself is of limited interest, but several of its derivatives are widely used preservatives and antimicrobials.

The European Chemicals Bureau (ECB) was the focal point for the data and assessment procedure on dangerous chemicals within the European Union (EU). The ECB was located in Ispra, Italy, within the Joint Research Centre (JRC) of the European Commission. In 2008 the ECB completed its mandate. Some of its activities were taken over by the European Chemicals Agency (ECHA); others remained within the Joint Research Centre. The history of the ECB has been published as a JRC technical report.

The Scientific Committee on Consumer Safety (SCCS) is one of the independent scientific committees managed by the Directorate-General for Health and Consumer Protection of the European Commission, which provide scientific advice to the commission on issues related to non-food issues. It is the successor to both the Scientific Committee on Consumer Products (SCCP) and the Scientific Committee on Cosmetic Products and Non-Food Products (SCCNFP).

The Scientific Committee on Health and Environmental Risks (SCHER) is one of the independent scientific committees managed by the Directorate-General for Health and Consumer Protection of the European Commission, which provide scientific advice to the Commission on issues related to consumer products.

<span class="mw-page-title-main">Formaldehyde releaser</span> Chemical compound used as a preservative that slowly releases formaldehyde.

A formaldehyde releaser, formaldehyde donor or formaldehyde-releasing preservative is a chemical compound that slowly releases formaldehyde. Formaldehyde-releasers are added to prevent microbial growth and extend shelf life. The intent of these compounds is that they release formaldehyde at levels that suppress microbial growth but sufficiently low to not threaten humans. The use of these chemicals in cosmetics has elicited controversy.

p-Chlorocresol, or 4-chloro-3-methylphenol (ClC6H3CH3OH), also known as p-chloro-m-cresol, is a potent disinfectant and antiseptic. It appears as a pinkish white crystalline solid and has a melting point of 64-66°C. It is also used as a preservative in cosmetics and medicinal products for both humans and animals. It is used as an active ingredient in some preparations of veterinary medicines for tropical, oral and parenteral use. Normally, the concentration of p-Chlorocresol in oral and parenteral veterinary products are 0.1-0.2%. Concentrations are higher (~0.5%) in tropical veterinary products. p-Chlorocresol contains microbial activity against both gram positive and gram negative bacteria and fungi.

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

Lilial is a chemical compound commonly used as a perfume in cosmetic preparations and laundry powders, often under the name butylphenyl methylpropional. It is an aromatic aldehyde, naturally occurring in crow-dipper and tomato plants, and produced synthetically in large scale. It was banned for use in cosmetics by the EU in March 2022 after being found to be harmful to fertility.

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

Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite in fact is not a real compound, but a mixture of salts that dissolve in water to give solutions composed of sodium and bisulfite ions. It appears in form of white or yellowish-white crystals with an odor of sulfur dioxide. Regardless of its ill-defined nature, sodium bisulfite is used in many different industries such as a food additive with E number E222 in the food industry, a reducing agent in the cosmetic industry, and a decomposer of residual hypochlorite used in the bleaching industry.

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

Iodopropynyl Butyl Carbamate (IPBC) is a water-soluble preservative used globally in the paints & coatings, wood preservatives, personal care, and cosmetics industries. IPBC is a member of the carbamate family of biocides. IPBC was invented in the 1970s and has a long history of effective use as an antifungal technology.

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

Galaxolide is a synthetic musk with a clean sweet musky floral woody odor used in fragrances. It is one of the musk components that perfume and cologne manufacturers use to add a musk odor to their products. Galaxolide was first synthesized in 1965, and used in the late 1960s in some fabric softeners and detergents. High concentrations were also incorporated in fine fragrances.

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

(Benzothiazol-2-ylthio)methyl thiocyanate (TCMTB) is a chemical compound classified as a benzothiazole.

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. ↑ Crow, W. D.; Leonard, Nelson J. (1965). "3-Isothiazolone-cis-3-Thiocyanoacrylamide Equilibria1,2". The Journal of Organic Chemistry. 30 (8): 2660–2665. doi:10.1021/jo01019a037.
  3. ↑ Collier PJ. Ramsey A. Waigh RD. Douglas KT. Austin P. Gilbert P.; Ramsey; Waigh; Douglas; Austin; Gilbert (1990). "Chemical reactivity of some isothiazolone biocides". Journal of Applied Bacteriology. 69 (4): 578–584. doi:10.1111/j.1365-2672.1990.tb01551.x. PMID   2292521.
  4. ↑ "Cosmetic Ingredient Review. Final Report on the Safety Assessment of Methylisothiazolinone and Methylchloroisothiazolinone". Journal of the American College of Toxicology. 11 (1): 75–128. 1992. doi: 10.3109/10915819209141993 . S2CID   208506926.
  5. ↑ A. Schnuch, J. Geier, W. Utur, P. J. Frosch: "Patch testing with preservatives, antimicrobials and industrial biocides. Results from a multicentre study", British Journal of Dermatology, 137(3), 467–476 (1998).
  6. ↑ A. C. De Groot, A. Herxheimer: "Isothiazolinone Preservative: Cause Of A Continuing Epidemic Of Cosmetic Dermatitis", The Lancet , Volume 333, Issue 8633, 314–316 (1989).
  7. ↑ European Scientific Committee on Cosmetic Products and Non-food Products Intended for Consumers (SCCNFP), adopted 2004
  8. ↑ SCCS (Scientific Committee on Consumer Safety), Opinion on Methylisothiazolinone (P94) – Submission II, 12 December 2013, SCCS/1521/13, revision of 27 March 2014 (PDF)
  9. ↑ Castanedo-Tardana, M. P.; Zug, K. A. (2013). "Methylisothiazolinone". Dermatitis: Contact, Atopic, Occupational, Drug. 24 (1): 2–6. doi:10.1097/DER.0b013e31827edc73. PMID   23340392. S2CID   220573338.
  10. ↑ "Why Methylisothiazolinone-Free Cleaning Products Matter", AspenClean.com
  11. ↑ Schwensen, J. F.; Menné Bonefeld, C.; Zachariae, C.; Agerbeck, C.; H.Petersen, T; Geisler, C.; E.Bollmann, U; Bester, K.; D.Johansen, J (2016-06-01). "Cross-reactivity between methylisothiazolinone, octylisothiazolinone and benzisothiazolinone using a modified local lymph node assay". British Journal of Dermatology. 176 (1): 176–183. doi:10.1111/bjd.14825. PMID   27343839. S2CID   207075221.
  12. ↑ https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_G-58_1-Oct-98.pdf [ bare URL PDF ]
  13. ↑ "European Commission - Press release - Consumers: Commission improves safety of cosmetics". europa.eu. Retrieved 2016-08-10.
  14. ↑ "Health Canada - "December 2015 Changes to the Cosmetic Ingredient Hotlist"". 2005-09-13.
  15. ↑ 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, 2016-07-23, retrieved 2021-08-13
  16. ↑ Commission Regulation (EU) 2017/1224 of 6 July 2017 amending Annex V to Regulation (EC) No 1223/2009 of the European Parliament and of the Council on cosmetic products, 2017-07-07, retrieved 2021-08-13
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