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]
home cleaning and car care products; laundry detergents, stain removers and fabric softeners;
industrial settings, for example in textile spin-finish solutions, leather processing solutions, preservation of fresh animal hides and skins
agriculture in pesticide formulations
gas and oil drilling in muds and packer fluids preservation.[4]: iv
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 hazardsEdit
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]
^ abcdGarcia-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.
^U.S. Environmental Protection Agency. September 29, 2005 EPA Reregistration Decision
^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.
^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)
^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.
^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)
^Scientific Committee on Consumer Safety (SCCS) Opinion on Benzisothiazolinone
^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)
LiteratureEdit
Wilfried Paulus: Directory of Microbicides for the Protection of Materials and Processes. Springer Netherland, Berlin 2006, ISBN1-4020-4861-0.
External linksEdit
Media related to Benzisothiazolinone at Wikimedia Commons
August 31, 2023
benzisothiazolinone, organic, compound, with, formula, c6h4sn, white, solid, structurally, related, isothiazole, part, class, molecules, called, isothiazolinones, widely, used, preservative, antimicrobial, namespreferred, iupac, name, benzothiazol, oneother, n. 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 Benzisothiazolinone NamesPreferred IUPAC name 1 2 Benzothiazol 3 2H oneOther names Benzisothiazolinone Benzisothiazolin 3 one BenzisothiazoloneIdentifiersCAS Number 2634 33 5 Y3D model JSmol Interactive imageAbbreviations BITBeilstein Reference 119510ChEBI CHEBI 167099 YChEMBL ChEMBL297304 YChemSpider 16567 YECHA InfoCard 100 018 292EC Number 220 120 9MeSH 1 2 benzisothiazoline 3 onePubChem CID 17520RTECS number DE4620000UNII HRA0F1A4R3CompTox Dashboard EPA DTXSID5032523InChI InChI 1S C7H5NOS c9 7 5 3 1 2 4 6 5 10 8 7 h1 4H H 8 9 YKey DMSMPAJRVJJAGA UHFFFAOYSA N YInChI 1 C7H5NOS c9 7 5 3 1 2 4 6 5 10 8 7 h1 4H H 8 9 Key DMSMPAJRVJJAGA UHFFFAOYACSMILES O C1c2ccccc2SN1PropertiesChemical formula C 7H 5N O SMolar mass 151 18 g mol 1Appearance white powderMelting point 158 C 316 F 431 K 1 Solubility in water 1 g LHazardsGHS labelling PictogramsSignal word DangerHazard statements H302 H315 H317 H318 H400Precautionary statements P261 P264 P270 P272 P273 P280 P301 P312 P302 P352 P305 P351 P338 P310 P321 P330 P332 P313 P333 P313 P362 P363 P391 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Usage 2 Health hazards 3 References 4 Literature 5 External linksUsage EditBenzisothiazolinone has a microbicide and a fungicide mode of action It is widely used as a preservative for example in emulsion paints caulks varnishes adhesives inks and photographic processing solutions home cleaning and car care products laundry detergents stain removers and fabric softeners industrial settings for example in textile spin finish solutions leather processing solutions preservation of fresh animal hides and skins agriculture in pesticide formulations gas and oil drilling in muds and packer fluids preservation 4 iv 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 EditGiven 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 References Edit a b 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 a b c d Garcia Hidalgo Elena Schneider Dovile von Goetz Natalie Delmaar Christiaan Siegrist Michael Hungerbuhler 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 Silva Vania Silva Catia 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 U S Environmental Protection Agency September 29 2005 EPA Reregistration Decision 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 Schwensen J F Lundov M D Bossi R Banerjee P Gimenez Arnau E Lepoittevin J P Liden 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 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Garcia Hidalgo Elena Sottas Virginie von Goetz Natalie Hauri Urs Bogdal Christian Hungerbuhler 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 ToxNet 1 2 Benzisothiazoline 3 one Diljit Kaur Knudsen Torkil Menne 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 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Scientific Committee on Consumer Safety SCCS Opinion on Benzisothiazolinone 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 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Literature EditWilfried Paulus Directory of Microbicides for the Protection of Materials and Processes Springer Netherland Berlin 2006 ISBN 1 4020 4861 0 External links Edit nbsp Media related to Benzisothiazolinone at Wikimedia Commons Retrieved from https en wikipedia org w index php title Benzisothiazolinone amp oldid 1170131478, wikipedia, wiki, book, books, library,
