Benzisothiazolinone

Last updated
Benzisothiazolinone
Benzisothiazolinone.svg
Benzisothiazolinone-from-xtal-3D-bs-17.png
Names
Preferred IUPAC name
1,2-Benzothiazol-3(2H)-one
Other names
Benzisothiazolinone, Benzisothiazolin-3-one, Benzisothiazolone
Identifiers
3D model (JSmol)
AbbreviationsBIT
119510
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.018.292 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 220-120-9
MeSH 1,2-benzisothiazoline-3-one
PubChem CID
RTECS number
  • DE4620000
UNII
  • InChI=1S/C7H5NOS/c9-7-5-3-1-2-4-6(5)10-8-7/h1-4H,(H,8,9) Yes check.svgY
    Key: DMSMPAJRVJJAGA-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H5NOS/c9-7-5-3-1-2-4-6(5)10-8-7/h1-4H,(H,8,9)
    Key: DMSMPAJRVJJAGA-UHFFFAOYAC
  • O=C1c2ccccc2SN1
Properties
C7H5NOS
Molar mass 151.18 g·mol−1
Appearancewhite powder
Melting point 158 °C (316 °F; 431 K) [1]
1 g/L
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Danger
H302, H315, H317, H318, H400
P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P333+P313, P362, P363, P391, 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 ?)

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. [2] [3] BIT is widely used as a preservative and antimicrobial. [4]

Contents

Usage

Benzisothiazolinone has a microbicide and a fungicide mode of action. It is widely used as a preservative, for example in:

In paints, it is commonly used alone or as a mixture with methylisothiazolinone. Typical concentrations in products are 200–400  ppm depending on the application area and the combination with other biocides. According to a study in Switzerland, 19% of the paints, varnishes and coatings contained BIT in 2000. The fraction in adhesives, sealants, plasters and fillers was shown at that time as 25%. [6] A later study in 2014 shows a dramatic rise in usage, to 95.8% of house paints. [7]

Home cleaning and other care products that are high in water are easily contaminated by microorganisms, so isothiazolinones are often used as a preservative in these products because they are good at combatting a broad array of bacteria, fungi, and yeasts. [3]

A Swiss investigation found that BIT is used in concentrations between 50 and 500 ppm in tattooing ink. [8] According to regulations in the EU and Switzerland, BIT cannot be used in cosmetics. However, it is allowed in the United States and Canada. [3]

Health hazards

Given sufficient dose and duration, dermal exposure can produce skin sensitization and allergic contact dermatitis, [9] and is classified as an irritant for skin and eyes. [1] BIT's low molar mass allows for it to penetrate the epidermis and then react with the skin macromolecules, which causes the irritation. [3] Benzisothiazolinone has also been linked with Systemic Contact Dermatitis via airborne contact. [10]

In 2012, the Scientific Committee on Consumer Safety in Europe found BIT's "sensitising potential is of concern...Sensitisation from related isothiazolinones is an important problem in consumers. This has occurred because there has been consumer exposure before safe levels of exposure relevant to sensitisation have been established. Benzisothiazolinone is a skin sensitiser in animal models with potency similar to methylisothiazolinone. Methylisothiazolinone, at 100 ppm (0.01%) in cosmetic products is causing contact allergy and allergic contact dermatitis in the consumer. Benzisothiazolinone is known to be a sensitiser in man and has induced sensitisation at circa 20 ppm in gloves." [11]

The opinion further states: "There is no information on what may be safe levels of exposure to benzisothiazolinone in cosmetic products from the point of view of sensitisation. Until safe levels of exposure have been established, the use of benzisothiazolinone in cosmetic products as a preservative or for other functions cannot be considered safe in relation to sensitisation."

Later, in 2013, researchers published a study that set out to derive the highest concentration of BIT in certain consumer products that would result in exposures below the No Expected Sensitization Induction Level (NESIL); that is, where normal use would yield a dose below the level at which skin sensitization might occur. The products under consideration were sunscreen, laundry detergent, dish soap, and spray cleaner; by way of calculation they derived BIT NESILs of 0.0075%, 0.035%, 0.035%, and 0.021%, respectively. They then performed a pilot examination via bulk sample analysis of one representative product from each category labelled as containing BIT. Their findings showed all BIT concentrations well below the derived NESIL, with 0.0009% and 0.0027% for sunscreen and dish soap, respectively, and no detection in the laundry detergent and spray cleaner products, meaning the concentration was at or below the limit of detection of 0.0006%. [12]

Related Research Articles

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<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.

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Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid. It is almost odorless and has a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. As it contains two alcohol groups, it is classed as a diol. An aliphatic diol may also be called a glycol. It is miscible with a broad range of solvents, including water, acetone, and chloroform. In general, glycols are non-irritating and have very low volatility.

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<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.

<span class="mw-page-title-main">Contact dermatitis</span> Inflammation from allergen or irritant exposure

Contact dermatitis is a type of acute or chronic inflammation of the skin caused by exposure to chemical or physical agents. Symptoms of contact dermatitis can include itchy or dry skin, a red rash, bumps, blisters, or swelling. These rashes are not contagious or life-threatening, but can be very uncomfortable.

<span class="mw-page-title-main">Quaternium-15</span> Salt used as a surfactant

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<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.

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Eyelid dermatitis is commonly related to atopic dermatitis or allergic contact dermatitis. Volatile substances, tosylamide, epoxy hardeners, insect sprays, and lemon peel oil may be implicated, with many cases of eyelid contact dermatitis being caused by substances transferred by the hands to the eyelids.

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

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<span class="mw-page-title-main">Metal allergy</span> Medical condition

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References

  1. 1 2 Record of 1,2-Benzisothiazol-3(2H)-one in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 22 October 2007.
  2. ↑ {{cite journal}}: Empty citation (help)
  3. 1 2 3 4 Garcia-Hidalgo, Elena; Schneider, Dovilé; von Goetz, Natalie; Delmaar, Christiaan; Siegrist, Michael; Hungerbühler, Konrad (2018). "Aggregate consumer exposure to isothiazolinones via household care and personal care products: Probabilistic modelling and benzisothiazolinone risk assessment". Environment International. 118: 245–256. Bibcode:2018EnInt.118..245G. doi:10.1016/j.envint.2018.05.047. PMID   29894934. S2CID   48364636.
  4. ↑ 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.
  5. ↑ U.S. Environmental Protection Agency. September 29, 2005 EPA Reregistration Decision
  6. ↑ Reinhard; et al. (2001). "Preservation of products with MCI/MI in Switzerland". Contact Dermatitis. 45 (5): 257–64. doi:10.1034/j.1600-0536.2001.450501.x. PMID   11722483. S2CID   21296570.
  7. ↑ Schwensen, J.F.; Lundov, M. D.; Bossi, R.; Banerjee, P.; Giménez-Arnau, E.; Lepoittevin, J. P.; Lidén, C.; Uter, W.; Yazar, K.; White, I. R.; Johansen, J.D. (2015). "Methylisothiazolinone and benzisothiazolinone are widely used in paint: a multicentre study of paints from five European countries". Contact Dermatitis. 72 (3): 127–38. doi:10.1111/cod.12322. PMID   25510184. S2CID   9651179.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ↑ Garcia-Hidalgo, Elena; Sottas, Virginie; von Goetz, Natalie; Hauri, Urs; Bogdal, Christian; Hungerbühler, Konrad (2017). "Occurrence and concentrations of isothiazolinones in detergents and cosmetics in Switzerland". Contact Dermatitis. 76 (2): 96–106. doi: 10.1111/cod.12700 . PMID   27862003. S2CID   3918533.
  9. ↑ ToxNet 1,2-Benzisothiazoline-3-one
  10. ↑ Diljit Kaur-Knudsen, Torkil Menné, Berit Christina Carlsen (2012). "Systemic Allergic Dermatitis Following Airborne Exposure to 1,2-Benzisothiazolin-3-one". Contact Dermatitis. 67 (5): 310–312. doi:10.1111/j.1600-0536.2012.02117.x. PMID   23039006. S2CID   35041455.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  11. ↑ Scientific Committee on Consumer Safety (SCCS) Opinion on Benzisothiazolinone
  12. ↑ Novick, R.M.; Nelson, M.L.; Unice, K. M.; Keenan, J. J.; Paustenbach; D. J. (2013). "Estimation of the Safe Use Concentrations of the Preservative 1,2-Benzisothiazolin-3-one (BIT) in Consumer Cleaning Products and Sunscreens". Food Chem. Toxicol. 56: 60–6. doi:10.1016/j.fct.2013.02.006. PMID   23429043.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Literature

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