Didecyldimethylammonium chloride
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| Preferred IUPAC name
N-Decyl-N,N-dimethyldecan-1-aminium chloride | |
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3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.027.751 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C22H48ClN | |
| Molar mass | 362.08 g/mol |
| Appearance | colorless solid |
| Density | 0.87 g/cm3 (20 °C) |
| Melting point | 88 °C (190 °F; 361 K) |
| Pharmacology | |
| D08AJ06 (WHO) | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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toxic |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Didecyldimethylammonium chloride (DDAC) is the quaternary ammonium salt with the formula (CH3)2N(C10H21)2Cl. The cation (CH3)2N(C10H21)+2 and chloride comprise this salt, which is a colorless solid.
DDAC is an antiseptic/disinfectant. Like related quat salts, it disrupts lipid bilayers. The bacteriostatic (prevent growth) or bactericidal (kill microorganism) activity of DDAC depends on its concentration and the growth phase of the microbial population.[3] 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.
Safety and environmental considerations
[edit]DDAC is of concern in waste water treatment because of its toxicity and resilience. [4] 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), when being fed at least 60 milligrams of disinfectant per kilogram of body weight, per day.[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][full citation needed] 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][irrelevant citation]
Europe and the United States differ on regulation for antimicrobials. Europe places all applied contact of antimicrobials under BPR while the United States breaks down contact into distinct categories. The FDA regulates drugs that come in contact with human and animals, while the EPA regulates drugs that come into contact with the environment.[9] DDAC is under a tolerance exception for objects that come into contact with food, in which concentration levels need to be under 200ppm, or 240ppm (applies to quaternary ammonium compounds).[10]
Human health is a concern as DDAC was given a toxicity rating of II during which rats were exposed to the chemical via oral route. DDAC has also been determined to be corrosive when put into direct contact with the eyes. There has been no drinking water study conducted between 2006 and 2017. [10]
A study conducted in 2024 measuring QAC levels in different water sources (including, but not limited to, tap water) in New York, USA, found that both bottled and tap water were contaminated with QAC's. QAC's are completely soluble in water which makes filtering out the chemicals difficult. Stormwater runoff contained the highest concentration of QAC's of up to 1000 ng/L. [11]
See also
[edit]- Dimethyldioctadecylammonium chloride – longer di-C18 analogue
References
[edit]- ^ a b c d e f g "Didecyl dimethyl ammonium chloride", Household Products Database, US Department of Health and Human Services, 2016
- ^ "didecyl(dimethyl)azanium;dimethyl(dioctyl)azanium;dichloride". PubChem. National Center for Biotechnology Information. Retrieved 23 July 2023.
- ^ 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.
- ^ Zhang, Chang; Cui, Fang; Zeng, Guang-Ming; Jiang, Min; Yang, Zhong-zhu; Yu, Zhi-Gang; Zhu, Meng-Ying; Shen, Liu-Qing (2015). "Quaternary ammonium compounds (QACs): A review on occurrence, fate and toxicity in the environment". Science of the Total Environment. 518–519: 352–362. Bibcode:2015ScTEn.518..352Z. doi:10.1016/j.scitotenv.2015.03.007. PMID 25770948.
- ^ 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.
- ^ 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.
- ^ Office of Prevention, Pesticides and Toxic Substances, US EPA (August 2006). "Reregistration Eligibility Decision for Aliphatic Alkyl Quaternaries (DDAC)". Epa739-R-06-008.
- ^ 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.
- ^ Luz, Anthony; DeLeo, Paul; Pechacek, Nathan; Freemantle, Mike (2020-10-01). "Human health hazard assessment of quaternary ammonium compounds: Didecyl dimethyl ammonium chloride and alkyl (C12–C16) dimethyl benzyl ammonium chloride". Regulatory Toxicology and Pharmacology. 116 104717. doi:10.1016/j.yrtph.2020.104717. ISSN 0273-2300. PMID 32640297.
- ^ a b Environmental Protection Agency (March 2017). "Didecyl Dimethyl Ammonium Chloride (DDAC) Final Work Plan" (PDF).
- ^ Li, Zhong-Min; Jeong, HuiHo; Kannan, Kurunthachalam (2025-08-15). "A survey of 27 quaternary ammonium compounds in surface water, drinking water, stormwater runoff, swimming pool water, and rainwater from New York State, USA". Water Research. 282 123736. Bibcode:2025WatRe.28223736L. doi:10.1016/j.watres.2025.123736. ISSN 0043-1354. PMID 40318284.
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