Chloroxylenol

Last updated

Chloroxylenol
Chloroxylenol.svg
Names
Preferred IUPAC name
4-Chloro-3,5-dimethylphenol [1]
Other names
para-Chloro-meta-xylenol, PCMX, 4-Chloro-3,5-dimethylphenol
Identifiers
3D model (JSmol)
1862539
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.631 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-793-8
KEGG
MeSH chloroxylenol
PubChem CID
RTECS number
  • ZE6850000
UNII
  • InChI=1S/C8H9ClO/c1-5-3-7(10)4-6(2)8(5)9/h3-4,10H,1-2H3 X mark.svgN
    Key: OSDLLIBGSJNGJE-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C8H9ClO/c1-5-3-7(10)4-6(2)8(5)9/h3-4,10H,1-2H3
    Key: OSDLLIBGSJNGJE-UHFFFAOYAY
  • Cc1cc(O)cc(C)c1Cl
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
D08AE05 ( WHO )
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H315, H317, H319
P280, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Contents

The discovery of chloroxylenol was the result of efforts to produce improved antiseptics that began at the end of the 1800s, when scientists gradually realized that more substituted and more lipophylic phenols are less toxic, less irritant and more powerful. [3] 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. [4] [5]

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 including Dettol. [6]

The World Health Organization lists a 4.8% solution of chloroxylenol as an essential medicine. [7] 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. [8]

The use of chloroxylenol has been increasing due to the removal of hexachlorophene [2] and later triclosan and others from world markets. [9] [5] It is currently used for control of bacteria, algae, and fungi in:

[4] [5]

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. [4]

EU

Chloroxylenol is allowed in cosmetics up to 0.5% [5]

Antimicrobial properties

Chloroxylenol is most effective against gram-positive bacteria. [8] It works by disruption of the cell wall and stopping the function of enzymes. [10] [11] [5] It is less effective than some other available agents. [12] [10] Testing has shown products containing chloroxylenol effective against the SARS-CoV-2 virus [13] and orthopoxviruses. [14]

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. [4] The European Union considers it to be a skin sensitizer. [9]

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. [15] [16] 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. [17]

Related Research Articles

A bactericide or bacteriocide, sometimes abbreviated Bcidal, is a substance which kills bacteria. Bactericides are disinfectants, antiseptics, or antibiotics. However, material surfaces can also have bactericidal properties based solely on their physical surface structure, as for example biomaterials like insect wings.

An antiseptic is an antimicrobial substance or compound that is applied to living tissue to reduce the possibility of sepsis, infection or putrefaction. Antiseptics are generally distinguished from antibiotics by the latter's ability to safely destroy bacteria within the body, and from disinfectants, which destroy microorganisms found on non-living objects.

<span class="mw-page-title-main">Sodium hypochlorite</span> Chemical compound (known in solution as bleach)

Sodium hypochlorite is an alkaline inorganic chemical compound with the formula NaOCl. It is commonly known in a dilute aqueous solution as bleach or chlorine bleach. It is the sodium salt of hypochlorous acid, consisting of sodium cations and hypochlorite anions.

A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a slightly different definition for biocides as "a diverse group of poisonous substances including preservatives, insecticides, disinfectants, and pesticides used for the control of organisms that are harmful to human or animal health or that cause damage to natural or manufactured products". When compared, the two definitions roughly imply the same, although the US EPA definition includes plant protection products and some veterinary medicines.

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

Chlorine dioxide is a chemical compound with the formula ClO2 that exists as yellowish-green gas above 11 °C, a reddish-brown liquid between 11 °C and −59 °C, and as bright orange crystals below −59 °C. It is usually handled as an aqueous solution. It is commonly used as a bleach. More recent developments have extended its applications in food processing and as a disinfectant.

<span class="mw-page-title-main">Disinfectant</span> Antimicrobial agent that inactivates or destroys microbes

A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than sterilization, which is an extreme physical or chemical process that kills all types of life. Disinfectants are generally distinguished from other antimicrobial agents such as antibiotics, which destroy microorganisms within the body, and antiseptics, which destroy microorganisms on living tissue. Disinfectants are also different from biocides—the latter are intended to destroy all forms of life, not just microorganisms. Disinfectants work by destroying the cell wall of microbes or interfering with their metabolism. It is also a form of decontamination, and can be defined as the process whereby physical or chemical methods are used to reduce the amount of pathogenic microorganisms on a surface.

<span class="mw-page-title-main">Benzalkonium chloride</span> Surfactant and antiseptic agent

Benzalkonium chloride, also known as alkyldimethylbenzylammonium chloride (ADBAC) and by the trade name Zephiran, is a type of cationic surfactant. It is an organic salt classified as a quaternary ammonium compound. ADBACs have three main categories of use: as a biocide, a cationic surfactant, and a phase transfer agent. ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-numbered alkyl chain lengths.

<span class="mw-page-title-main">Chlorhexidine</span> Disinfectant and antiseptic

Chlorhexidine is a disinfectant and antiseptic with the molecular formula C22H30Cl2N10, which is used for skin disinfection before surgery and to disinfect surgical instruments. It is also used for cleaning wounds, preventing dental plaque, treating yeast infections of the mouth, and to keep urinary catheters from blocking. It is used as a liquid or a powder. It is commonly used in salt form, either the gluconate or the acetate.

<span class="mw-page-title-main">Paraben</span> Class of chemical compounds; esters of parahydroxybenzoic acid

Parabens are chemicals that are commonly used as preservatives in cosmetic and pharmaceutical products. Chemically, they are a series of parahydroxybenzoates or esters of parahydroxybenzoic acid. Research is being conducted to evaluate the potential health implications of paraben usage.

An antimicrobial is an agent that kills microorganisms (microbicide) or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals are used against fungi. They can also be classified according to their function. The use of antimicrobial medicines to treat infection is known as antimicrobial chemotherapy, while the use of antimicrobial medicines to prevent infection is known as antimicrobial prophylaxis.

<span class="mw-page-title-main">Povidone-iodine</span> Antiseptic solution

Povidone-iodine (PVP-I), also known as iodopovidone, is an antiseptic used for skin disinfection before and after surgery. It may be used both to disinfect the hands of healthcare providers and the skin of the person they are caring for. It may also be used for minor wounds. It may be applied to the skin as a liquid, an ointment or a powder.

<span class="mw-page-title-main">Hand sanitizer</span> Alternative to hand washing

Hand sanitizer is a liquid, gel, or foam used to kill viruses, bacteria, and other microorganisms on the hands. It can also come in the form of a cream, spray, or wipe. While hand washing with soap and water is generally preferred, hand sanitizer is a convenient alternative in settings where soap and water are unavailable. However, it is less effective against certain pathogens like norovirus and Clostridioides difficile and cannot physically remove harmful chemicals. Improper use, such as wiping off sanitizer before it dries, can also reduce its effectiveness, and some sanitizers with low alcohol concentrations are less effective. Additionally, frequent use of hand sanitizer may disrupt the skin's microbiome and cause dermatitis.

Dakin's solution is a dilute solution of sodium hypochlorite and other stabilizing ingredients, traditionally used as an antiseptic, e.g. to cleanse wounds in order to prevent infection. The preparation was for a time called also Carrel–Dakin solution or Carrel–Dakin fluid.

<span class="mw-page-title-main">Lysol</span> Cleaning products brand name

Lysol is a brand of American cleaning and disinfecting products distributed by Reckitt, which markets the similar Dettol or Sagrotan in other markets. The line includes liquid solutions for hard and soft surfaces, air treatment, and hand washing. The active ingredient in many Lysol products is benzalkonium chloride, but the active ingredient in the Lysol "Power and Free" line is hydrogen peroxide. Lysol has been used since its invention in the late 19th century as a household and industrial cleaning agent, and previously as a medical disinfectant.

<span class="mw-page-title-main">Bleach</span> Chemicals used to whiten or disinfect

Bleach is the generic name for any chemical product that is used industrially or domestically to remove color from fabric or fiber or to disinfect after cleaning. It often refers specifically to a dilute solution of sodium hypochlorite, also called "liquid bleach".

p-Chlorocresol, or 4-chloro-3-methylphenol (ClC6H3CH3OH), also known as p-chloro-m-cresol, is a potent disinfectant and antiseptic. It appears as a pinkish white crystalline solid. It is also used as a preservative in cosmetics and medicinal products for both humans and animals. It is used as an active ingredient in some preparations of veterinary medicines for tropical, oral and parenteral use. Normally, the concentration of p-Chlorocresol in oral and parenteral veterinary products are 0.1-0.2%. Concentrations are higher (~0.5%) in tropical veterinary products. p-Chlorocresol contains microbial activity against both gram positive and gram negative bacteria and fungi.

<span class="mw-page-title-main">Alcohols (medicine)</span> Alcohols used as antiseptics, disinfectants or antidotes

Alcohols, in various forms, are used medically as an antiseptic, disinfectant, and antidote. Alcohols applied to the skin are used to disinfect skin before a needle stick and before surgery. They may also be used as a hand sanitizer; to clean other areas; and in mouthwashes. Taken by mouth or injected into a vein, ethanol is used to treat methanol or ethylene glycol toxicity when fomepizole is not available.

<span class="mw-page-title-main">Chlorine-releasing compounds</span>

Chlorine-releasing compounds, also known as chlorine base compounds, is jargon to describe certain chlorine-containing substances that are used as disinfectants and bleaches. They include the following chemicals: sodium hypochlorite, chloramine, halazone, and sodium dichloroisocyanurate. They are widely used to disinfect water and medical equipment, and surface areas as well as bleaching materials such as cloth. The presence of organic matter can make them less effective as disinfectants. They come as a liquid solution, or as a powder that is mixed with water before use.

Creolin is a generic name for disinfectants whose composition varies according to origin. It is extracted from the dry distillation of wood. The residue remaining in the autoclave vessel is a dark, syrupy mass called creosote, which is composed mainly of phenolic acid and cresylic acid. The original composition of creolin is a creosote tar oil, caustic soda, soaps, and very little water. It is of low technology and a very powerful disinfectant.

Dettol antiseptic liquid is a product produced by the Dettol Brand for Reckitt. It is light yellow in color in the concentrated form but, as several of the ingredients are insoluble in water, it produces a milky emulsion of oil droplets when diluted with water, exhibiting the ouzo effect. Chloroxylenol comprises 4.8% of the admixture, with pine oil, isopropanol, castor oil, soap and water.

References

  1. CID 2723 from PubChem
  2. 1 2 3 4 Ascenzi JM (1996). "Chloroxylenol: an old-new antimicrobial". Handbook of disinfectants and antiseptics. New York: M. Dekker. ISBN   978-0-8247-9524-5. Archived from the original on 2017-09-23.
  3. de Solis NM (1993). Effect of plasmids that confer preservative-resistance on the performance of bacteria in preservative efficacy tests (Doctoral thesis). University College London. p. 31.
  4. 1 2 3 4 R.E.D Facts, Chloroxylenol, United States Environmental Protection Agency (EPA), September 1994.
  5. 1 2 3 4 5 "Chloroxylenol - brand name list from Drugs.com" (PDF). www.industrialchemicals.gov.au. Archived from the original on 2017-08-28.
  6. "Chloroxylenol - brand name list from Drugs.com". www.drugs.com. Archived (PDF) from the original on 2023-03-12.
  7. World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. 1 2 World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 324. hdl:10665/44053. ISBN   9789241547659.
  9. 1 2 "Chemical Profile: Chloroxylenol". www.madesafe.org. 25 May 2023. Archived from the original on 2023-11-24.
  10. 1 2 Mahon CR, Lehman DC, Manuselis G Jr (2014). Textbook of Diagnostic Microbiology (5 ed.). Elsevier Health Sciences. p. 67. ISBN   9780323292627. Archived from the original on 2017-01-13.
  11. Bednarek RS, Nassereddin A, Ramsey ML (2021). "Skin Antiseptics". StatPearls. StatPearls. PMID   29939630.
  12. 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. S2CID   205427305.
  13. Ijaz K, Whitehead K, Srinivasan V, Jones C, Nims R, Charlesworth B (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. PMC   7246051 . PMID   32461067 . Retrieved 2021-01-31.
  14. Butcher W, Ulaeto D (2005). "Contact inactivation of orthopoxviruses by household disinfectants". Journal of Applied Microbiology. 99 (2). Wiley: 279–284. doi:10.1111/j.1365-2672.2005.02601.x. ISSN   1364-5072. PMID   16033458. S2CID   43085296.
  15. "Nine things you didn't know could poison your pet". Archived from the original on 2022-02-24.
  16. Dettol liquid at drugs.com Archived 2015-09-24 at the Wayback Machine
  17. Narelle Towie (23 May 2009). "Cane toad poison banned". Perth Now. Archived from the original on 15 January 2013. Retrieved 2 February 2013.

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