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

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%. [5] A later study in 2014 shows a dramatic rise in usage, to 95.8% of house paints. [6]

Home cleaning and other care products that are high in water are easily contaminated by microorganisms, so isothiazolinones are often used as a preservatives in these products because they are good at combatting a broad array of bacteria, fungi, and yeasts. [2]

A Swiss investigation found that BIT is used in concentrations between 50 and 500 ppm in tattooing ink. [7] According to regulations in the EU and Switzerland, BIT cannot be used in cosmetics. However, it is allowed in the United States and Canada. [2]

Health hazards

Given sufficient dose and duration, dermal exposure can produce skin sensitization and allergic contact dermatitis, [8] 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. [2] Benzisothiazolinone has also been linked with Systemic Contact Dermatitis via airborne contact. [9]

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." [10]

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%, 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%. [11]

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.

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

Oxybenzone or benzophenone-3 or BP-3 is an organic compound. It is a pale-yellow solid that is readily soluble in most organic solvents. Oxybenzone belongs to the class of aromatic ketones known as benzophenones. It is widely used in plastics, toys, furniture finishes, and other products to limit UV degradation.

<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> Human disease

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">Paraben</span> Class of chemical compounds; esters of parahydroxybenzoic acid

Parabens are a class of widely used preservatives in cosmetic and pharmaceutical products. Chemically, they are a series of parahydroxybenzoates or esters of parahydroxybenzoic acid. Parabens are effective preservatives in many types of formulas. These compounds, and their salts, are used primarily for their bactericidal and fungicidal properties. They are found in shampoos, commercial moisturizers, shaving gels, personal lubricants, topical/parenteral pharmaceuticals, suntan products, makeup, and toothpaste. They are also used as food preservatives.

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

Quaternium-15 is a quaternary ammonium salt that has been used as a surfactant and preservative. It acts as an antimicrobial agent because it slowly releases formaldehyde, which is a preservative with biocidal properties.

<span class="mw-page-title-main">Patch test</span> Medical test to determine substances causing allergic reactions

A patch test is a diagnostic method used to determine which specific substances cause allergic inflammation of a patient's skin.

Cocamidopropyl betaine (CAPB) is a mixture of closely related organic compounds derived from coconut oil and dimethylaminopropylamine. CAPB is available as a viscous pale yellow solution and it is used as a surfactant in personal care products and animal husbandry. The name reflects that the major part of the molecule, the lauric acid group, is derived from coconut oil. Cocamidopropyl betaine to a significant degree has replaced cocamide DEA.

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

Triethanolamine, or TEA, is an organic compound with the chemical formula N(CH2CH2OH)3. It is a colourless viscous liquid. It is both a tertiary amine and a triol. A triol is a molecule with three alcohol groups. Approximately 150,000 tonnes were produced in 1999. It is a colourless compound although samples may appear yellow because of impurities.

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

Allergic contact dermatitis (ACD) is a form of contact dermatitis that is the manifestation of an allergic response caused by contact with a substance; the other type being irritant contact dermatitis (ICD).

<span class="mw-page-title-main">Lotion</span> Skin treatment preparation

Lotion is a low-viscosity topical preparation intended for application to the skin. By contrast, creams and gels have higher viscosity, typically due to lower water content. Lotions are applied to external skin with bare hands, a brush, a clean cloth, or cotton wool.

<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.

<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.

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.

Perfume intolerance or perfume allergy is a condition wherein people exhibit sensitivity or allergic reactions to ingredients in some perfumes and some other fragrances. It is a form of multiple chemical sensitivity, a more general phenomenon for this diagnosis.

<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">Tetramethyl acetyloctahydronaphthalenes</span> Chemical compound

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

Nickel allergy or nickel allergic contact dermatitis (Ni-ACD) is a form of allergic contact dermatitis (ACD) caused by exposure to the chemical element nickel. It typically causes a rash that is red and itchy and that may be bumpy or scaly. The main treatment is avoiding contact with nickel-releasing metals, such as inexpensive jewelry.

<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. 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. doi:10.1016/j.envint.2018.05.047. PMID   29894934. S2CID   48364636.
  3. ↑ 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.
  4. ↑ U.S. Environmental Protection Agency. September 29, 2005 EPA Reregistration Decision
  5. ↑ 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.
  6. ↑ 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)
  7. ↑ 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.
  8. ↑ ToxNet 1,2-Benzisothiazoline-3-one
  9. ↑ 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)
  10. ↑ Scientific Committee on Consumer Safety (SCCS) Opinion on Benzisothiazolinone
  11. ↑ 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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