Chemistry:Chloroxylenol
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| Names | |
|---|---|
| Preferred IUPAC name
4-Chloro-3,5-dimethylphenol[1] | |
| Other names
para-Chloro-meta-xylenol, PCMX, 4-Chloro-3,5-dimethylphenol
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| Identifiers | |
3D model (JSmol)
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| 1862539 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| EC Number |
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| KEGG | |
| MeSH | chloroxylenol |
PubChem CID
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| RTECS number |
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| UNII | |
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| Properties | |
| C8H9ClO | |
| Molar mass | 156.61 g·mol−1 |
| Melting point | 115 °C (239 °F; 388 K) |
| Boiling point | 246 °C (475 °F; 519 K) |
| 300 mg/L [2] | |
| Solubility in alcohols | soluble |
| Solubility in Ethers | soluble |
| Solubility in Benzene | soluble |
| log P | 3.377 |
| Acidity (pKa) | 9.76 |
| Basicity (pKb) | 4.24 |
| Pharmacology | |
| 1=ATC code }} | D08AE05 (WHO) |
| Hazards | |
| GHS pictograms | 
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| GHS Signal word | WARNING |
| H302, H315, H317, H319 | |
| P280, P305+351+338 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Chloroxylenol, also known as para-chloro-meta-xylenol (PCMX), is a chlorine substituted phenol with a white to off-white appearance and a phenolic odor. The discovery of chloroxylenol was the result of efforts to produce improved antiseptics that began at the end of the 1800s. First synthesized in Germany in 1923, it was borne out of the study of coal tar components that began a decade earlier.[2]
Synthesis
Other chlorine substituted phenols are contaminated with dioxins resulting from their synthesis. USEPA found chloroxylenol synthesis was not affected.[3][4]
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.[2] Chloroxylenol is used in a number of formulations and under a number of brand names, most notably Dettol.[5]
The World Health Organization lists a 4.8% solution of chloroxylenol as an essential medicine.[6] 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.[7]
The use of chloroxylenol has been increasing due to the removal of hexachlorophene[2] and later triclosan and others from world markets.[8][4] It is currently used for control of bacteria, algae, and fungi in:
- 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 USA in 1959. Chloroxylenol containing products must not be used in any manner that allows contamination of water.[3]
EU
Chloroxylenol is allowed in cosmetics up to 0.5%[4]
Antimicrobial properties
Chloroxylenol is most effective against gram-positive bacteria.[7] It works by disruption of the cell wall and stopping the function of enzymes.[9][10][4] It is less effective than some other available agents.[11][9] Testing has shown products containing chloroxylenol effective against the SARS-CoV-2 virus[12] and orthopoxviruses.[13]
Toxicology
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.[3] The European Union considers it to be a skin sensitizer.[8]
Related compounds
- 4-chloro-3-methylphenol (PCMC) – similar use / similar structure
- 2-Chloro-m-cresol – Structural similarity
References
- ↑ CID 2723 from PubChem
- ↑ 2.0 2.1 2.2 2.3 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.
- ↑ 3.0 3.1 3.2 3.3 R.E.D Facts, Chloroxylenol, United States Environmental Protection Agency (EPA), September 1994.
- ↑ 4.0 4.1 4.2 4.3 4.4 "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.
- ↑ "Chloroxylenol - brand name list from Drugs.com". https://www.drugs.com/ingredient/chloroxylenol.html.
- ↑ World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
- ↑ 7.0 7.1 WHO Model Formulary 2008. World Health Organization. 2009. p. 324. ISBN 9789241547659.
- ↑ 8.0 8.1 "Chemical Profile: Chloroxylenol". 25 May 2023. https://madesafe.org/blogs/viewpoint/chemical-profile-chloroxylenol.
- ↑ 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.
- ↑ Bednarek, R. S.; Nassereddin, A.; Ramsey, M. L. (2021). "Skin Antiseptics". StatPearls. StatPearls. https://www.ncbi.nlm.nih.gov/books/NBK507853/.
- ↑ 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.
- ↑ 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.
- ↑ 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.
External links
- "Chloroxylenol". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/chloroxylenol.
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