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Didecyldimethylammonium chloride

Didecyldimethylammonium chloride
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 Edit this at Wikidata
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 checkY
    Key: RUPBZQFQVRMKDG-UHFFFAOYSA-M checkY
  • 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
Appearance liquid[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).
checkY verify (what is checkY☒N ?)

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

References

  1. ^ a b c d e f g "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. ^ a b c 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. 50. NIH: 163–170. Bibcode:2014RepTx..50..163M. 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.
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