Didecyldimethylammonium chloride

Last updated
Didecyldimethylammonium chloride
Didecyldimethylammonium chloride.png
Names
Preferred IUPAC name
N-Decyl-N,N-dimethyldecan-1-aminium chloride
Other names
  • DDAC
  • Dimethyldidecylammonium chloride [1] [2]
  • 1-Decanaminium [1]
  • N-decyl-N,N-dimethyl-, chloride [1]
  • Didecyldimethylammonium chloride [1]
  • Didecyl dimethyl ammonium chloride [1]
  • Quaternium-12 [1]

Ammonium, didecyldimethyl-, chloride [1]

Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.027.751 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C22H48N.ClH/c1-5-7-9-11-13-15-17-19-21-23(3,4)22-20-18-16-14-12-10-8-6-2;/h5-22H2,1-4H3;1H/q+1;/p-1 Yes check.svgY
    Key: RUPBZQFQVRMKDG-UHFFFAOYSA-M Yes check.svgY
  • InChI=1/C22H48N.ClH/c1-5-7-9-11-13-15-17-19-21-23(3,4)22-20-18-16-14-12-10-8-6-2;/h5-22H2,1-4H3;1H/q+1;/p-1
    Key: RUPBZQFQVRMKDG-REWHXWOFAJ
  • [Cl-].C(CCCCC[N+](C)(CCCCCCCCCC)C)CCCC
Properties
C22H48ClN
Molar mass 362.08 g/mol
Appearanceliquid [3]
Density 0.87 g/cm3 (20 °C) [3]
Pharmacology
D08AJ06 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
corrosive [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Didecyldimethylammonium chloride (DDAC) is a quaternary ammonium compound used as antiseptic/disinfectant. It causes the disruption of intermolecular interactions and the dissociation of lipid bilayers. The bacteriostatic (prevent growth) or bactericide (kill microorganism) activity of DDAC depends on its concentration and the growth phase of the microbial population. [4] It is a broad spectrum biocidal against bacteria and fungi and can be used as disinfectant cleaner for linen, recommended for use in hospitals, hotels and industries. It is also used in gynaecology, surgery, ophthalmology, pediatrics, OT, and for the sterilization of surgical instruments, endoscopes and surface disinfection.

In mice this disinfectant was found to cause infertility and birth defects when combined with Alkyl (60% C14, 25% C12, 15% C16) dimethyl benzyl ammonium chloride (ADBAC). [5] [6] These studies contradict the older toxicology data set on quaternary ammonia compounds which was reviewed by the U.S. Environmental Protection Agency (U.S. EPA) and the EU Commission. [7] In addition, DDAC, as well as other quaternary ammonia compounds, can lead to the acquisition of resistance by microorganisms when employed in sub-lethal concentrations. [8]

See also

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">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.

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">Quaternary ammonium cation</span> Polyatomic ions of the form N(–R)₄ (charge +1)

In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.

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

Cetrimonium bromide ([(C16H33)N(CH3)3]Br; cetyltrimethylammonium bromide; hexadecyltrimethylammonium bromide; CTAB) is a quaternary ammonium surfactant.

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

Cetylpyridinium chloride (CPC) is a cationic quaternary ammonium compound used in some types of mouthwashes, toothpastes, lozenges, throat sprays, breath sprays, and nasal sprays. It is an antiseptic that kills bacteria and other microorganisms. It has been shown to be effective in preventing dental plaque and reducing gingivitis. It has also been used as an ingredient in certain pesticides. Though one study seems to indicate cetylpyridinium chloride does not cause brown tooth stains, at least one mouthwash containing CPC as an active ingredient bears the warning label "In some cases, antimicrobial rinses may cause surface staining to teeth," following a failed class-action lawsuit brought by customers whose teeth were stained.

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

Benzethonium chloride, also known as hyamine is a synthetic quaternary ammonium salt. This compound is an odorless white solid, soluble in water. It has surfactant, antiseptic, and anti-infective properties, and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in cosmetics and toiletries such as soap, mouthwashes, anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride is also used in the food industry as a hard surface disinfectant.

<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">Mercuric amidochloride</span> Chemical compound

Mercuric amidochloride is an inorganic compound with the formula Hg(NH2)Cl.

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

Dequalinium is a quaternary ammonium cation and bolaamphiphile commonly available as the dichloride salt. It is useful as an antiseptic and disinfectant. The bromide, iodide, acetate, and undecenoate salts are known as well. Dequalinium chloride is the active ingredient of several medications.

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

Hexamidine is an antiseptic and disinfectant. Hexomedine is the trade name of a diisethionate solution (1/1.000) of hexamidine. Hexamidine is used primarily as its diisethionate salt, which is more water-soluble than the dihydrochloride. The dihydrochloride was first synthesized and patented as a trypanocide for May & Baker in 1939. Its amoebicidal properties emerged in the 1990s. The exact mechanism of its biocidal action is unknown, but presumed similar to quaternary ammonium compounds, involving binding to the negatively charged lipid membranes of pathogens. Hexamidine and its shorter congener, propamidine, are used as antiseptics and preservatives in pharmaceuticals and cosmetics. They are particularly used for the topical treatment of acanthamoebiasis.

Stearalkonium chloride is a type of benzalkonium chloride which is used as an anti-static agent, a surfactant and an antimicrobial. It is an ingredient in some cosmetics and hair care products, particularly conditioners. It was originally designed by the fabric industry for use as a fabric softener.

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.

Benzododecinium bromide is a quaternary ammonium compound used as antiseptic and disinfectant. It is highly soluble in water and has properties of cationic surfactant.

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

Tetramethylammonium chloride is one of the simplest quaternary ammonium salts, with four methyl groups tetrahedrally attached to the central N. The chemical formula (CH3)4N+Cl is often abbreviated further as Me4N+Cl. It is a hygroscopic colourless solid that is soluble in water and polar organic solvents. Tetramethylammonium chloride is a major industrial chemical, being used widely as a chemical reagent and also as a low-residue bactericide in such processes as hydrofracking. In the laboratory, it has fewer synthetic chemical applications than quaternary ammonium salts containing longer N-alkyl substituents, which are used extensively as phase-transfer catalysts.

Alkaline copper quaternary, usually abbreviated ACQ, is a type of water-based wood preservative product containing a soluble copper(II) complex and quaternary ammonium alkyl- or aryl-substituted compounds ("quats"). Thus the product was originally called ammoniacal copper/quaternary ammonium.

Polymers with the ability to kill or inhibit the growth of microorganisms such as bacteria, fungi, or viruses are classified as antimicrobial agents. This class of polymers consists of natural polymers with inherent antimicrobial activity and polymers modified to exhibit antimicrobial activity. Polymers are generally nonvolatile, chemically stable, and can be chemically and physically modified to display desired characteristics and antimicrobial activity. Antimicrobial polymers are a prime candidate for use in the food industry to prevent bacterial contamination and in water sanitation to inhibit the growth of microorganisms in drinking water.

An antimicrobial surface is coated by an antimicrobial agent that inhibits the ability of microorganisms to grow on the surface of a material. Such surfaces are becoming more widely investigated for possible use in various settings including clinics, industry, and even the home. The most common and most important use of antimicrobial coatings has been in the healthcare setting for sterilization of medical devices to prevent hospital associated infections, which have accounted for almost 100,000 deaths in the United States. In addition to medical devices, linens and clothing can provide a suitable environment for many bacteria, fungi, and viruses to grow when in contact with the human body which allows for the transmission of infectious disease.

References

  1. 1 2 3 4 5 6 7 "Didecyl dimethyl ammonium chloride", Household Products Database, US Department of Health and Human Services, 2016
  2. "didecyl(dimethyl)azanium;dimethyl(dioctyl)azanium;dichloride". PubChem . National Center for Biotechnology Information . Retrieved 23 July 2023.
  3. 1 2 3 Record of didecyldimethylammonium chloride in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2 November 2007.
  4. Kampf G (2018). "Didecyldimethylammonium Chloride". Antiseptic Stewardship. Cham.: Springer. pp. 371–394. doi:10.1007/978-3-319-98785-9_11. ISBN   978-3-319-98785-9.
  5. Hunt P (June 2008). "Lab disinfectant harms mouse fertility. Patricia Hunt interviewed by Brendan Maher". Nature. 453 (7198): 964. doi: 10.1038/453964a . PMID   18563110.
  6. Melin VE, Potineni H, Hunt P, Griswold J, Siems B, Werre SR, Hrubec TC (December 2014). "Exposure to common quaternary ammonium disinfectants decreases fertility in mice". Reproductive Toxicology. NIH. 50: 163–170. doi:10.1016/j.reprotox.2014.07.071. PMC   4260154 . PMID   25483128.
  7. Office of Prevention, Pesticides and Toxic Substances, US EPA (August 2006). "Reregistration Eligibility Decision for Aliphatic Alkyl Quaternaries (DDAC)". Epa739-R-06-008.
  8. Pedreira A, Vázquez JA, García MR (2022-04-07). "Kinetics of Bacterial Adaptation, Growth, and Death at Didecyldimethylammonium Chloride sub-MIC Concentrations". Frontiers in Microbiology. 13: 758237. doi: 10.3389/fmicb.2022.758237 . PMC   9023358 . PMID   35464917.