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. 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]

Contents

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:

[3] [4]

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 Research Articles

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, commonly known in a dilute solution as (chlorine) bleach, is an inorganic chemical compound with the formula NaOCl, consisting of a sodium cation and a hypochlorite anion. It may also be viewed as the sodium salt of hypochlorous acid. The anhydrous compound is unstable and may decompose explosively. It can be crystallized as a pentahydrate NaOCl·5H
2
O
, a pale greenish-yellow solid which is not explosive and is stable if kept refrigerated.

Cresols are a group of aromatic organic compounds. They are widely-occurring phenols which may be either natural or manufactured. They are also categorized as methyl phenols. Cresols commonly occur as either solids or liquids because their melting points are generally close to room temperature. Like other types of phenols, they are slowly oxidized by exposure to air, and the resulting impurities often give the samples a yellow to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "coal tar" smell. The name "cresol" is an adduct of phenol and their traditional source, creosote.

<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 sterilize 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.

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 or a powder.

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

Hand sanitizer is a liquid, gel or foam generally used to kill many viruses/bacteria/microorganisms on the hands. In most settings, hand washing with soap and water is generally preferred. Hand sanitizer is less effective at killing certain kinds of germs, such as norovirus and Clostridium difficile, and unlike hand washing, it cannot physically remove harmful chemicals. People may incorrectly wipe off hand sanitizer before it has dried, and some are less effective because their alcohol concentrations are too low.

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 colour (whitening) from fabric or fiber or to clean or to remove stains in a process called bleaching. It often refers specifically to a dilute solution of sodium hypochlorite, also called "liquid bleach".

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

Polyhexanide is a polymer used as a disinfectant and antiseptic. In dermatological use, it is spelled polihexanide (INN) and sold under the names Lavasept, Serasept, Prontosan, and Omnicide. PHMB has been shown to be effective against Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, Candida albicans, Aspergillus brasiliensis, enterococci, and Klebsiella pneumoniae.

A virucide is any physical or chemical agent that deactivates or destroys viruses. The substances are not only virucidal but can be also bactericidal, fungicidal, sporicidal or tuberculocidal.

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 within medicine 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 be used both to disinfect the skin of the person and as hand sanitizer of the healthcare providers. They can also be used 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">Iodine (medical use)</span> Topical antiseptic and supplement

Iodine is used to treat and prevent iodine deficiency and as an antiseptic. For iodine deficiency it can be given by mouth or injection into a muscle. As an antiseptic it may be used on wounds that are wet or to disinfect the skin before surgery.

<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.

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, Joseph M. (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. 1 2 3 4 R.E.D Facts, Chloroxylenol, United States Environmental Protection Agency (EPA), September 1994.
  4. 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.
  5. "Chloroxylenol - brand name list from Drugs.com". www.drugs.com. Archived (PDF) from the original on 2023-03-12.
  6. 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.
  7. 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.
  8. 1 2 "Chemical Profile: Chloroxylenol". www.madesafe.org. Archived from the original on 2023-11-24.
  9. 1 2 Mahon, Connie R.; Lehman, Donald C.; Manuselis, George Jr. (2014). Textbook of Diagnostic Microbiology (5 ed.). Elsevier Health Sciences. p. 67. ISBN   9780323292627. Archived from the original on 2017-01-13.
  10. Bednarek, R. S.; Nassereddin, A.; Ramsey, M. L. (2021). "Skin Antiseptics". StatPearls. StatPearls. PMID   29939630.
  11. 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.
  12. 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. PMC   7246051 . PMID   32461067 . Retrieved 2021-01-31.
  13. 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. S2CID   43085296.

Commons-logo.svg Media related to Chloroxylenol at Wikimedia Commons