Chemistry:Chloroxylenol

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Chloroxylenol, also known as para-chloro-meta-xylenol, is an organic compound with the formula (CH
3)
2ClC
6H
2OH. It is a chlorine-substituted xylenol. The compound is a colorless solid although impure samples can appear off-white. It has a phenolic odor. It is a common antiseptic.[1]


Uses

Formulations containing chloroxylenol are used in hospitals and households as antiseptics, disinfectants, and sanitizers. It is commonly used in antibacterial soaps, wound-cleansing, and other household antiseptic applications.[1] Chloroxylenol is used in a number of formulations and under a number of brand names including Dettol.[2]

It is on the World Health Organization's List of Essential Medicines.[3] When diluted, this chloroxylenol preparation is used as an antiseptic and disinfectant, and for skin disinfection. Diluted with alcohol, it is suitable for disinfecting medical instruments.[4]

Chloroxylenol has been substituted for hexachlorophene and triclosan, which have been removed from world markets.[5][6] It is currently used for control of bacteria, algae, and fungi in:[7][6]

  • Adhesive and sealant products
  • Construction products
  • Lubricant and grease products
  • Paint and coating products
  • Plastic and polymer products
  • Wash tanks
  • Diaper pails
  • Laundry equipment
  • Bedding
  • Pet living quarters
  • Hospitals
  • Personal care products
  • Cleaning and furniture care products
  • Fabric, textile and leather products
  • Ink, toner and colorant products

United States

Chloroxylenol was first introduced to the United States in 1959. Chloroxylenol containing products must not be used in any manner that allows contamination of water.[7]

European Union

The European Union allows chloroxylenol in cosmetics up to 0.5%.[6][8]

Antimicrobial properties

Chloroxylenol is most effective against gram-positive bacteria.[4] It works by disruption of the cell wall and stopping the function of enzymes.[9][10][6] It is less effective than some other available agents.[1][9] Testing has shown products containing chloroxylenol effective against the SARS-CoV-2 virus[11] and orthopoxviruses.[12] A meta-analysis found insufficient evidence to determine whether exposure creates bacterial resistance.[13]

Synthesis

Chloroxylenol is produced by chlorination of the corresponding xylenol.[14]

Toxicology

It "is safe as used in cosmetics".[15] Chloroxylenol is generally slightly to moderately toxic to humans (but causes severe eye irritation), is practically non-toxic to birds, toxic to fish, and moderately toxic to freshwater invertebrates.[7] The European Union considers it to be a skin sensitizer.[5]

Chloroxylenol may also be harmful to smaller vertebrates, especially cats. Phenolic compounds are of particular concern to felines because cats are unable to fully metabolize them. A cat may swallow the product by licking its paws after it has come into contact with it.[16][17] Products containing chloroxylenol such as Dettol have been previously administered with a spray bottle on unwanted pests or invasive species such as cane toads, which die shortly after being sprayed with the phenolic compound. The use of chloroxylenol-containing Dettol as an agent for pest control was banned in Western Australia by the Department of Environment and Conservation in 2011.[18]

History

The discovery of chloroxylenol was the result of efforts to produce improved antiseptics that began at the end of the 1800s, when it was realized that more substituted and more lipophilic phenols are less toxic, less irritating, and more powerful.[19] First synthesized in Germany in 1923, it was born out of the study of coal tar components that began a decade earlier.[20]

References

  1. ↑ 1.0 1.1 1.2 Digison, MB (2007). "A review of anti-septic agents for pre-operative skin preparation.". Plastic Surgical Nursing 27 (4): 185–9; quiz 190–1. doi:10.1097/01.psn.0000306182.50071.e2. PMID 18165724. 
  2. ↑ "Chloroxylenol - brand name list from Drugs.com". https://www.drugs.com/ingredient/chloroxylenol.html. 
  3. ↑ The selection and use of essential medicines, 2025: WHO Model List of Essential Medicines, 24th list. Geneva: World Health Organization. 2025. doi:10.2471/B09474. License: CC BY-NC-SA 3.0 IGO. 
  4. ↑ 4.0 4.1 WHO Model Formulary 2008. World Health Organization. 2009. p. 324. ISBN 9789241547659. 
  5. ↑ 5.0 5.1 "Chemical Profile: Chloroxylenol". 25 May 2023. https://madesafe.org/blogs/viewpoint/chemical-profile-chloroxylenol. 
  6. ↑ 6.0 6.1 6.2 6.3 "Chloroxylenol - brand name list from Drugs.com". https://www.industrialchemicals.gov.au/sites/default/files/2022-01/EVA00061%20-%20Evaluation%20statement%20-%2014%20January%202022%20%5B1871%20KB%5D.pdf. 
  7. ↑ 7.0 7.1 7.2 R.E.D Facts, Chloroxylenol, United States Environmental Protection Agency (EPA), September 1994.
  8. ↑ "Cosmetic Products Regulation, Annex V - Allowed Preservatives". https://echa.europa.eu/cosmetics-preservatives/-/legislationlist/details/EU-COSM_PROD-ANX_V_ALLOW_PRESERV-100.001.631-VSK-0104EE. 
  9. ↑ 9.0 9.1 Mahon, Connie R.; Lehman, Donald C.; Manuselis, George Jr. (2014) (in en). Textbook of Diagnostic Microbiology (5 ed.). Elsevier Health Sciences. p. 67. ISBN 9780323292627. https://books.google.com/books?id=VloMBAAAQBAJ&pg=PA67. 
  10. ↑ Bednarek, R. S.; Nassereddin, A.; Ramsey, M. L. (2021). "Skin Antiseptics". StatPearls. StatPearls. https://www.ncbi.nlm.nih.gov/books/NBK507853/. 
  11. ↑ Ijaz, Khalid; Whitehead, Kelly; Srinivasan, Vanita; Jones, Chris; Nims, Raymond; Charlesworth, Bruce (2020-05-24). "Microbicidal actives with virucidal efficacy against SARS-CoV-2". American Journal of Infection Control 48 (8): 972–973. doi:10.1016/j.ajic.2020.05.015. PMID 32461067. PMC 7246051. https://www.ajicjournal.org/article/S0196-6553(20)30313-8/fulltext. Retrieved 2021-01-31. 
  12. ↑ Butcher, W.; Ulaeto, D. (2005). "Contact inactivation of orthopoxviruses by household disinfectants". Journal of Applied Microbiology (Wiley) 99 (2): 279–284. doi:10.1111/j.1365-2672.2005.02601.x. ISSN 1364-5072. PMID 16033458. 
  13. ↑ Maillard, Jean-Yves (2022). "Impact of benzalkonium chloride, benzethonium chloride and chloroxylenol on bacterial antimicrobial resistance". Journal of Applied Microbiology 133 (6): 3322–3346. doi:10.1111/jam.15739. PMID 35882500. 
  14. ↑ An overview of chlorination methods: Mostafa, Mohamed A. B.; Bowley, Rosalind M.; Racys, Daugirdas T.; Henry, Martyn C.; Sutherland, Andrew (2017). "Iron(III)-Catalyzed Chlorination of Activated Arenes". The Journal of Organic Chemistry 82 (14): 7529–7537. doi:10.1021/acs.joc.7b01225. PMID 28661157. 
  15. ↑ Cherian, Priya; Bergfeld, Wilma F.; Belsito, Donald V.; Cohen, David E.; Klaassen, Curtis D.; Liebler, Daniel C.; Rettie, Allan E.; Ross, David et al. (2023). "Chloroxylenol". International Journal of Toxicology 42 (3_suppl): 22S–23S. doi:10.1177/10915818231204263. PMID 37769700. 
  16. ↑ "Nine things you didn't know could poison your pet". https://www.stuff.co.nz/life-style/life/77412595/nine-things-you-didnt-know-could-poison-your-pet. 
  17. ↑ Dettol liquid at drugs.com
  18. ↑ Narelle Towie (23 May 2009). "Cane toad poison banned". Perth Now. http://www.perthnow.com.au/news/cane-toad-poison-banned/story-e6frg12c-1225715177178. 
  19. ↑ de Solis, Nilka M. G. (1993). Effect of plasmids that confer preservative-resistance on the performance of bacteria in preservative efficacy tests (Doctoral thesis). University College London. p. 31.
  20. ↑ Ascenzi, Joseph M. (1996). "Chloroxylenol: an old-new antimicrobial". Handbook of disinfectants and antiseptics. New York: M. Dekker. ISBN 978-0-8247-9524-5. https://books.google.com/books?id=tFPW4D70BmgC&pg=PA265. 



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