Triclosan

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Triclosan
IUPAC name

5-chloro-2-(2,4-dichlorophenoxy)phenol
Other names

2,4,4'-trichloro-2'-hydroxydiphenyl ether, 5-chloro-(2,4-dichlorophenoxy)phenol, trichloro-2'-hydroxydiphenyl ether, CH-3565, Lexol 300, Irgasan DP 300
Identifiers
CAS number 3380-34-5 YesY
PubChem 5564
ChemSpider 5363 YesY
UNII 4NM5039Y5X YesY
DrugBank DB08604
KEGG D06226 YesY
ChEBI CHEBI:164200 YesY
ChEMBL CHEMBL849 YesY
ATC code D08AE04,
D09AA06 (medicated dressing)
Jmol-3D images Image 1
Properties
Molecular formula C12H7Cl3O2
Molar mass 289.54 g mol−1
Appearance White solid
Density 1.49 g/cm3
Melting point

55-57 °C
Boiling point

120 °C, 393 K, 248 °F
Hazards
MSDS MSDS
NFPA 704
NFPA 704.svg
1
2
0
Flash point 162.2 °C (324.0 °F)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Triclosan is an antibacterial and antifungal agent. It is a polychloro phenoxy phenol. Though many products contain triclosan, there is no evidence according to the Food and Drug Administration (FDA) that triclosan provides an extra benefit to health beyond its anti-gingivitis effect in toothpaste.[1] However, studies by the Environmental Protection Agency (EPA) found triclosan to be an effective antibacterial.[2] Triclosan safety is currently under review by the FDA[1] and Health Canada.[3]

Contents

Chemical structure and properties [edit]

This organic compound is a white powdered solid with a slight aromatic/phenolic odor. It is a chlorinated aromatic compound that has functional groups representative of both ethers and phenols. Phenols often show antibacterial properties. Triclosan is only slightly soluble in water, but soluble in ethanol, methanol, diethyl ether, and strongly basic solutions such as a 1 M sodium hydroxide solution. Triclosan can be synthesized from 2,4-dichlorophenol.

Some common impurities are: 2,4-dichlorophenol, 3-chlorophenol, 4-chlorophenol, 2,3,7,8-tetrachlorodibenzo-p-dioxin, 2,3,7,8-tetrachlorodibenzo-p-furan, 2,8-dichlorobenzo-furan, 2,8-dichlorobenzo-p-dioxin, 1,3,7-trichlorodibenzo-p-dioxin and 2,4,8-trichlorodibenzo-furan

Synthesis [edit]

2,4,4'-trichloro-2'-methoxydiphenyl ether is treated with aluminium chloride in benzene under reflux.

Triclosan can be synthesized through a three-step process starting with 1-(2-hydroxyethyl)pyrrolidin-2-one. The 1-(2-hydroxyethyl)pyrrolidin-2-one is to be dehydrated with either zinc or calcium oxide into 1-vinylpyrrolidin-2-one.[4] Then, 1-vinylpyrrolidin-2-one can be reacted with 5-chloro-2-(2,4-dichlorophenoxy)phenyl acrylate in n-heptane to form triclosan.[5]

Reactions [edit]

It can be used to produce 2-(2,4-dichloro-phenoxy)-4,5-dichloro-phenol at 20 °C with the reagent sulfuryl chloride.

Uses [edit]

Triclosan has been used since 1972, and it is present in soaps (0.10-1.00%), deodorants, toothpastes, mouth washes, and cleaning supplies,[6] and is infused in an increasing number of consumer products, such as kitchen utensils, toys, bedding, socks, and trash bags.[7] Triclosan has been shown to be effective in reducing and controlling bacterial contamination on the hands and on treated products. More recently, showering or bathing with 2% triclosan has become a recommended regimen in surgical units for the decolonization of patients whose skin is carrying methicillin-resistant Staphylococcus aureus (MRSA)[8] following the successful control of MRSA outbreaks in several clinical settings. Use in surgical units is effective with a minimum contact time of approximately 2 minutes.[9][10]

Triclosan is regulated by the U.S. Food and Drug Administration, the Environmental Protection Agency, and the European Union. During wastewater treatment, a portion of triclosan is degraded, while the remaining adsorbs to sewage sludge or exits the plant in wastewater effluent.[11][12] In the environment, triclosan may be degraded by microorganisms or react with sunlight, forming other compounds, which include between 3 and 12% of chlorophenols and dioxin (In particular, 2,8-dichlorodibenzo-p-dioxin (external) (2,8-DCDD) and 2,4-dichlorophenol (2,4-DCP) are produced. Both also are photolabile and, thus, are intermediates.), or it may adsorb to particles that settle out of the water column and form sediment.[11][13] Triclosan was found in Greifensee sediment that was over 30 years old, suggesting that triclosan is degraded or removed slowly in sediment.[11]

The use of triclosan as an additive for plastic production for use in food packages has not been approved by the European Commission (EC).[14]

Triclosan also has been employed as an effective selective agent in molecular cloning. Bacteria host transformed by plasmids harboring a triclosan resistant mutant FabI gene (mFabI) as a selectable marker can grow in presence of high dose of triclosan in the culture media. [15]

Mechanism of action [edit]

At in-use concentrations, triclosan acts as a biocide, with multiple cytoplasmic and membrane targets.[16] At lower concentrations, however, triclosan appears bacteriostatic and is seen to target bacteria mainly by inhibiting fatty acid synthesis. Triclosan binds to bacterial enoyl-acyl carrier protein reductase enzyme (ENR), which is encoded by the gene FabI. This binding increases the enzyme's affinity for nicotinamide adenine dinucleotide (NAD+). This results in the formation of a stable ternary complex of ENR-NAD+-triclosan, which is unable to participate in fatty acid synthesis. Fatty acids are necessary for reproducing and building cell membranes. Humans do not have an ENR enzyme, and thus are not affected. Some bacterial species can develop low-level resistance to triclosan at its lower bacteriostatic concentrations because of FabI mutations, which results in a decrease of triclosan's effect on ENR-NAD+ binding, as shown in Escherichia coli and Staphylococcus aureus.[17][18] Another way for these bacteria to gain low-level resistance to triclosan is to overexpress FabI.[19] Some bacteria have innate resistance to triclosan at low, bacteriostatic levels, such as Pseudomonas aeruginosa, which possesses multi-drug efflux pumps that "pump" triclosan out of the cell.[20] Other bacteria, such as some of the Bacillus genus, have alternative FabI genes (FabK) to which triclosan does not bind and hence are less susceptible.

Formation of dioxin in surface water [edit]

The use of triclosan in household antibacterial products introduces the chemical to surface waters where it can degrade to a non-toxic[21] type of dioxin. The dioxin-like compound that formed when triclosan degraded in sunlight and wastewater chlorine treatment were analyzed in sediment cores by University of Minnesota researchers.[22]

Resistance concerns [edit]

An article coauthored by Stuart Levy in the August 6, 1998 issue of Nature[23] warned that triclosan's overuse could cause resistant strains of bacteria to develop, in much the same way that antibiotic-resistant bacterial strains are emerging. In 2003, the Scottish Sunday Herald newspaper reported that some UK supermarkets and other retailers were considering phasing out products containing triclosan.[24]

It has since been shown that while the laboratory method used by Levy was not effective in predicting bacterial resistance for biocides like triclosan, triclosan does reduce species diversity, kills off efficient TCS degrader species (see citation's Table 4), and that it should be considered that "degradation of an ecosystem may rearrange the competitive hierarchy".[25] At least seven peer-reviewed and published studies have been conducted demonstrating that triclosan is not significantly associated with bacterial resistance over the short term, including one study coauthored by Levy.[26] However, the major concern over resistant strains is not that they will alter resistance profiles over the short term. The concern is that superbugs will evolve against which no bactericide can be used. For example, as noted above, triclosan is effective against MRSA. However, overuse of triclosan could lead to MRSA that is also triclosan-resistant.[citation needed]

Some level of triclosan resistance can occur in some microorganisms, but the larger concern is with the potential for cross-resistance or co-resistance to other antimicrobials. Studies investigating this possibility have been limited.[27] The European Commission Scientific Committee on Consumer Safety (SCCS) concludes that to date, there is no evidence that using triclosan leads to an increase in antibiotic resistance. However it is too early to say that triclosan exposure never leads to microbial resistance, as there is not yet enough information to make a full risk analysis.[28]

Health concerns [edit]

Triclosan is used in a variety of common household products, including soaps, mouthwashes, dish detergents, toothpastes, deodorants, and hand sanitizers.[29] In the United States, manufacturers of products containing triclosan must indicate it on the label.

Triclosan is a chlorinated aromatic compound with antibacterial, antifungal and antiviral properties (sold under several trade names, including UltraFresh, Amicor, and BioFresh). Triclosan is also a component in some pesticides, mattresses, insulation, and underlayments that install under various types of flooring, including laminate, wood, glued down, and engineered wood, and carpeting for the purpose of slowing or stopping the growth of bacteria, fungi, and mildew. For example, some high density sound-suppressing underlayments, foam floor underlayments and rebond carpet pads are treated with triclosan. Triclosan penetrates the skin on contact and enters the bloodstream [30] .

Allergy [edit]

A 2010 study found that children who had higher exposure to triclosan had more hay fever. This may be because exposure to bacteria reduces allergies, as predicted by the hygiene hypothesis and not toxicology of the triclosan itself. This would also occur with chlorhexidine gluconate and PCMX, among other antibacterial agents.[31][32][33] Other studies have linked triclosan to allergic contact dermatitis in some individuals.[34][35]

By-products [edit]

In August 2009, the Canadian Medical Association asked the Canadian government to ban triclosan use in household products under concerns of creating bacterial resistance and producing dangerous side products (chloroform).[36]

Triclosan also reacts with the free chlorine in tap water to produce lesser amounts of other compounds, like 2,4-dichlorophenol.[37] Most of these intermediates convert into dioxins upon exposure to UV radiation (from the sun or other sources). Although small amounts of dioxins are produced, some dioxins are extremely toxic and are very potent endocrine disruptors. They are also chemically stable, so that they are eliminated from the body slowly (they can bioaccumulate to dangerous levels), and they persist in the environment for a long time.

Triclosan is chemically somewhat[ambiguous] similar to the dioxin class of compounds. Its production leads to small amounts of residual polychlorinated dioxins, and polychlorinated furans in the products that are produced with it.[citation needed]

The American Dental Association published a response to the concerns stemming from the Virginia Tech study stating that the study is not relevant to toothpaste.[37][38]

Environment [edit]

Triclosan is toxic to aquatic bacteria at levels found in the environment. Triclosan inhibits photosynthesis in diatom algae which are responsible for a large part of the photosynthesis on Earth.[39]

Endocrine disruption [edit]

A 2006 study concluded that low doses of triclosan act as an endocrine disruptor in the North American bullfrog.[40] The hypothesis proposed is that triclosan blocks the metabolism of thyroid hormone because it chemically mimics thyroid hormone and binds to the hormone receptor sites, blocking them, so that normal hormones cannot be used. A study between 2003 and 2006 concluded that triclosan (as an endocrine disruptor) affects the immune system and showed a positive association with allergy or hay fever diagnosis.[41] Another study in 2000 offered the result that low amount of triclosan can be absorbed through skin and can enter the bloodstream.[42]

Triclosan has also been found in both the bile of fish living downstream from waste-water-processing plants and in human milk.[43] The negative effects of triclosan on the environment and its questionable benefits in toothpastes[44] have led to the Swedish Naturskyddsföreningen to recommend not using triclosan in toothpaste.[45] Another 2009 study demonstrated that triclosan exposure significantly impacts thyroid hormone concentrations in the male juvenile rats.[46]

Triclosan is also showing up in dolphins near South Carolina and Florida in concentrations known to disrupt hormones, growth, and development in other animals.[47]

However, a 4-year study of possible effects of triclosan (0.3%) in toothpaste on thyroid hormone function found no effect of triclosan on thyroid hormone concentration in sera of adult human subjects. [48]

Muscle contraction [edit]

Triclosan has been reported to impair excitation-contraction coupling in cardiac and skeletal muscle function in mice.[49]

Possible breakdown into carcinogenic metabolite [edit]

Two reports by the same authors suggest that triclosan can combine with chlorine in tap water to form chloroform[not in citation given],[37] which the United States Environmental Protection Agency classifies as a probable human carcinogen, meaning it likely causes cancer. These intermediates can be cleaved to form chlorophenols that can react with free chlorine to form trihalomethanes, such as chloroform.[50] As a result, triclosan was the target of a UK cancer alert, even though the study showed that the amount of chloroform generated was less than amounts often present in chlorinated drinking water.

Alternatives [edit]

A comprehensive analysis from the University of Michigan School of Public Health indicated that plain soaps are just as effective as consumer-grade antibacterial soaps with triclosan in preventing illness and removing bacteria from the hands.[51]

Nonorganic antibiotics and organic biocides are effective alternatives to triclosan, such as silver and copper ions and nanoparticles.[52]

See also [edit]

References [edit]

  1. ^ a b "Triclosan: What Consumers Should Know". U S Food and Drug Administration. 8 April 2010. Retrieved 13 April 2010. 
  2. ^ http://www.epa.gov/oppsrrd1/REDs/factsheets/triclosan_fs.htm
  3. ^ "Toxic chemical monitoring program gets $500M". CBC. 4 October 2011. 
  4. ^ Kahn, A.P. Production of N-Vinyl Pyrrolidone. US Patent 63970, Apr 1, 2004.
  5. ^ Plochocka, K. Polymeric Delivery and Release Systems for Oral Care Actives. US Patent 6,315,987, Nov 13, 2001.
  6. ^ ""The Fate and Removal of Triclosan during Wastewater Treatment" A. Thompson, P. Griffin, R. Stuetz and E. Cartmell. Water Environment Research. Vol. 77, No. 1, Emerging Micropollutants in Treatment Systems (Jan. - Feb., 2005), pp. 63-67. Published by: Water Environment Federation". Retrieved March 13, 2013. 
  7. ^ Record in the Household Products Database of NLM
  8. ^ Coia JE, Duckworth GJ, Edwards DI, et al. (2006). "Guidelines for the control and prevention of meticillin-resistant Staphylococcus aureus (MRSA) in healthcare facilities". J. Hosp. Infect. 63 Suppl 1: S1–44. doi:10.1016/j.jhin.2006.01.001. PMID 16581155. 
  9. ^ Brady LM, Thomson M, Palmer MA, Harkness JL (1990). "Successful control of endemic MRSA in a cardiothoracic surgical unit". Med. J. Aust. 152 (5): 240–5. PMID 2255283. 
  10. ^ Zafar AB, Butler RC, Reese DJ, Gaydos LA, Mennonna PA (1995). "Use of 0.3% triclosan (Bacti-Stat) to eradicate an outbreak of methicillin-resistant Staphylococcus aureus in a neonatal nursery". American journal of infection control 23 (3): 200–8. doi:10.1016/0196-6553(95)90042-X. PMID 7677266. 
  11. ^ a b c Singer H, Muller S, Tixier C, Pillonel L. (2002). "Triclosan: occurrence and fate of a widely used biocide in the aquatic environment: field measurements in wastewater treatment plants, surface waters, and lake sediments.". Environ Sci Technol. 36 (23): 4998–5004. doi:10.1021/es025750i. PMID 12523412. 
  12. ^ Heidler J, Halden RU. (2007). "Mass balance assessment of triclosan removal during conventional sewage treatment.". Chemosphere 66 (2): 362–369. doi:10.1016/j.chemosphere.2006.04.066. PMID 16766013. 
  13. ^ Latch DE, Packer JL, Stender BL, VanOverbeke J, Arnold WA, McNeill K (2005). "Aqueous photochemistry of triclosan: formation of 2,4-dichlorophenol, 2,8-dichlorodibenzo-p-dioxin, and oligomerization products". Environ. Toxicol. Chem. 24 (3): 517–25. doi:10.1897/04-243R.1. PMID 15779749. 
  14. ^ COMMISSION DECISION of 19 March 2010 concerning the non-inclusion of 2,4,4’-trichloro-2’-hydroxydiphenyl ether in the Union list of additives which may be used in the manufacture of plastic materials and articles intended to come into contact with foodstuffs under Directive 2002/72/EC 23.3.2010 Official Journal of the European Union
  15. ^ Jang, CW; Magnuson, T (2013). "A novel selection marker for efficient DNA cloning and recombineering in E. coli.". PloS one 8 (2): e57075. doi:10.1371/journal.pone.0057075. PMID 23437314. 
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  17. ^ Heath RJ, Rubin JR, Holland DR, Zhang E, Snow ME, Rock CO (1999). "Mechanism of triclosan inhibition of bacterial fatty acid synthesis". J. Biol. Chem. 274 (16): 11110–4. doi:10.1074/jbc.274.16.11110. PMID 10196195. 
  18. ^ Fan F, Yan K, Wallis NG, et al. (2002). "Defining and combating the mechanisms of triclosan resistance in clinical isolates of Staphylococcus aureus". Antimicrob. Agents Chemother. 46 (11): 3343–7. doi:10.1128/AAC.46.11.3343-3347.2002. PMC 128739. PMID 12384334. 
  19. ^ Slater-Radosti C, Van Aller G, Greenwood R, et al. (2001). "Biochemical and genetic characterization of the action of triclosan on Staphylococcus aureus". J. Antimicrob. Chemother. 48 (1): 1–6. doi:10.1093/jac/48.1.1. PMID 11418506. 
  20. ^ Chuanchuen R, Karkhoff-Schweizer RR, Schweizer HP (2003). "High-level triclosan resistance in Pseudomonas aeruginosa is solely a result of efflux". American journal of infection control 31 (2): 124–7. doi:10.1067/mic.2003.11. PMID 12665747. 
  21. ^ Wisk, Joseph D.; Cooper, Keith R. (1990). "Comparison of the toxicity of several polychlorinated dibenzo-p-dioxins and 2,3,7,8-tetrachlorodibenzofuran in embryos of the Japanese medaka (Oryzias latipes)". Chemosphere 20 (3–4): 361. doi:10.1016/0045-6535(90)90067-4. 
  22. ^ . doi:10.1021/es1001105.  Missing or empty |title= (help)
  23. ^ McMurry LM, Oethinger M, Levy SB (1998). "Triclosan targets lipid synthesis". Nature 394 (6693): 531–2. doi:10.1038/28970. PMID 9707111. 
  24. ^ Supermarkets to ban toxic detergent Rob Edwards, Sunday Herald, 02 November 2003
  25. ^ McBain AJ, Bartolo RG, Catrenich CE, et al. (2003). "Exposure of sink drain microcosms to triclosan: population dynamics and antimicrobial susceptibility". Appl. Environ. Microbiol. 69 (9): 5433–42. doi:10.1128/AEM.69.9.5433-5442.2003. PMC 194980. PMID 12957932. 
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  27. ^ Yazdankhah SP, Scheie AA, Høiby EA, et al. (2006). "Triclosan and antimicrobial resistance in bacteria: an overview". Microb. Drug Resist. 12 (2): 83–90. doi:10.1089/mdr.2006.12.83. PMID 16922622. 
  28. ^ Triclosan and Antibiotics resistance summary by GreenFacts of an opion by the European Commission Scientific Committee on Consumer Safety (March 2010)
  29. ^ Triclosan at Household Products Database, U.S. Department of Health and Human Services
  30. ^ Freaky Clean: Chemical in Antibacterial Soap Weakens Muscle Function; By Alexandra SifferlinAug. 15, 2012; healthland.time.com/2012/08/15/freaky-clean-chemical-in-antibacterial-soap-weakens-muscle-function/#ixzz2O64QDbRl
  31. ^ "Antibacterial Soaps: Being Too Clean Can Make People Sick, Study Suggests". Science Daily. Nov. 30, 2010. 
  32. ^ Clayton, EM.; Todd, M.; Dowd, JB.; Aiello, AE. (Nov 2010). "The Impact of Bisphenol A and Triclosan on Immune Parameters in the US Population, NHANES 2003-2006". Environ Health Perspect 119 (3): 390–396. doi:10.1289/ehp.1002883. PMC 3060004. PMID 21062687. 
  33. ^ "New Questions Raised On Chemicals In Soaps, Plastics : Shots - Health News Blog : NPR". npr.org. Retrieved 2010-11-30. 
  34. ^ Bhutani, T.; Jacob, SE. (May 2009). "Triclosan: a potential allergen in suture-line allergic contact dermatitis". Dermatol Surg 35 (5): 888–9. doi:10.1111/j.1524-4725.2009.01151.x. PMID 19389086. 
  35. ^ Campbell, L.; Zirwas, MJ. (Dec 2006). "Triclosan". Dermatitis 17 (4): 204–7. doi:10.2310/6620.2006.06014. PMID 17150172. 
  36. ^ Yang, Jeniffer (2009-08-21). "Experts concerned about dangers of antibacterial products". Globe and Mail. Retrieved 2009-08-25. 
  37. ^ a b c Rule KL, Ebbett VR, Vikesland PJ (2005). "Formation of chloroform and chlorinated organics by free-chlorine-mediated oxidation of triclosan". Environ. Sci. Technol. 39 (9): 3176–85. doi:10.1021/es048943. PMID 15926568. 
  38. ^ "ADA.org: ADA News: Triclosan study not relevant to toothpaste". ada.org. Archived from the original on 2007-10-24. Retrieved 2010-08-16. 
  39. ^ Ricart M, Guasch H, Alberch M, et al. (November 2010). "Triclosan persistence through wastewater treatment plants and its potential toxic effects on river biofilms". Aquatic Toxicology 100 (4): 346–53. doi:10.1016/j.aquatox.2010.08.010. PMID 20855117. 
  40. ^ Nik Veldhoen, Rachel C. Skirrow, Heather Osachoff, Heidi Wigmore, David J. Clapson, Mark P. Gunderson, Graham Van Aggelen and Caren C. Helbing (December 2006). "The bactericidal agent triclosan modulates thyroid hormone-associated gene expression and disrupts postembryonic anuran development". Aquatic Toxicology 80 (3): 217–227. doi:10.1016/j.aquatox.2006.08.010. PMID 17011055. 
  41. ^ Erin M. Rees Clayton, Megan Todd, Jennifer Beam Dowd, Allison E. Aiello (August 2010). "The Impact of Bisphenol A and Triclosan on Immune Parameters in the U.S. Population, NHANES 2003–2006". Environ Health Perspect 119 (3): 390–396. doi:10.1289/ehp.1002883. PMC 3060004. PMID 21062687. 
  42. ^ Moss T, Howes D, Williams FM. (April 2000). "Percutaneous penetration and dermal metabolism of triclosan (2,4, 4'-trichloro-2'-hydroxydiphenyl ether)". Food Chem Toxicol 38 (4): 361–370. doi:10.1016/S0278-6915(99)00164-7. PMID 10722890. 
  43. ^ Adolfsson-Erici M, Pettersson M, Parkkonen J, Sturve J. (March 2002). "Triclosan, a commonly used bactericide found in human milk and in the aquatic environment in Sweden". Chemosphere 46 (9–10): 1485–1489. doi:10.1016/S0045-6535(01)00255-7. PMID 12002480. 
  44. ^ Edvardsson S, Burman. L G, AdolfssonErici. M, Bäckman. N. (August 2005). "Risker och nytta med triklosan i tandkräm" (– Scholar search). Tandläkartidningen 97 (10): 58–64. [dead link]
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  46. ^ Zorrilla, L. M.; Gibson, E. K.; Jeffay, S. C.; Crofton, K. M.; Setzer, W. R.; Cooper, R. L.; Stoker, T. E. (2008). "The Effects of Triclosan on Puberty and Thyroid Hormones in Male Wistar Rats". Toxicological Sciences 107 (1): 56–64. doi:10.1093/toxsci/kfn225. PMID 18940961. 
  47. ^ "Germ-killing chemical from soaps, toothpaste building up in dolphins". 2009-08-11. Retrieved 2011-04-11. 
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  49. ^ Cherednichenko, G.; Zhang, R.; Bannister, R. A.; Timofeyev, V.; Li, N.; Fritsch, E. B.; Feng, W.; Barrientos, G. C. et al. (2012). "Triclosan impairs excitation-contraction coupling and Ca2+ dynamics in striated muscle". Proceedings of the National Academy of Sciences. doi:10.1073/pnas.1211314109. 
  50. ^ Fiss, E. M.; Rule, K. L.; Vikesland, P. J. Formation of Chloroform and Other Chlorinated Byproducts by Chlorination of Triclosan-Containing Antibacterial Products. Environ. Sci. Technol. 2007, 41, 2387-2394.
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