DIDECYLDIMETHYLAMMONIUM CHLORIDE

Synonyms:

7173-51-5; Didecyl dimethyl ammonium chloride; Didecyldimethylammonium chloride; N-decyl-N,N-dimethyldecan-1-aminium chloride; Astop; DDAC; Quaternium 12; Arquad 10; Bardac 22; Britewood Q; Dimethyldidecylammonium chloride; Bio-Dac; Quaternium-12; Odex Q; Quartamin D 10E; Quartamin D 10P; Nissan Cation 2DB; Timbercote 2000; Slaoff 91; Aliquat 203; Querton 210CL; 1-Decanaminium, N-decyl-N,N-dimethyl-, chloride; Dodigen 1881; Bardac 2270E; Calgon H 130; Caswell No. 331A; Maquat 4480E; Bardac 2250; Bardac 2280; H 130 (molluscicide); Arquad 210-50; Bio-dac 50-22; Tret-O-Lite XC 507; UNII-JXN40O9Y9B; DIDECYLDIMETHYLAMMONIUMCHLORIDE; DIDECYLDIMONIUM CHLORIDE; BTC 99; DDC 80; didecyl dimethylammonium chloride; BTCO 1010; D 10P; BTC 1010; N-Decyl-N,N-dimethyl-1-decanaminium chloride; Ammonium, didecyldimethyl-, chloride; EINECS 230-525-2; EPA Pesticide Chemical Code 069149; JXN40O9Y9B
didecyl(dimethyl)azanium;chloride; CHEBI:79935; 1-Decanaminium, N-decyl-N,N-dimethyl-, chloride (1:1); Acticide; Sporekill; KleenGrow; Britewood XL; Acticide DDQ; Catiogen DDM; Cation DDC; Catiogen DDM-PG; Asepas 3; Septapav KhS 70; Acticide DDQ 40; Microbiocide B 74; Stenquat 1010; Arquad 210; Cation DDC 50; Cation DDC-80; Macrotrol MT 200; Microbiocide N 750; New Des 50; Bardac 2240; Kamin RM 2D50A; K-Sanit BP 80; Didecyldimethylammonium chloride; Di decyl di methyl ammonium chloride; Didecyl dimethyl ammonium chloride; Didecyldimethyl ammonium chloride; DİDESİLDİMETİLAMONYUM KLORÜR; DİDESİL DİMETİL AMONYUM KLORÜR; Dİ DESİL Dİ METİL AMONYUM KLORÜR; DİDESİLDİMETİLAMONYUM KLORİT; DİDESİL DİMETİL AMONYUM KLORİT; Dİ DESİL Dİ METİL AMONYUM KLORİT

DIDECYLDIMETHYLAMMONIUM CHLORIDE

Didecyldimethylammonium chloride

Didecyldimethylammonium chloride
Didecyldimethylammonium chloride.png
Names
IUPAC name
didecyl-dimethylammonium chloride
Other names
DDAC
Dimethyldidecylammonium chloride[1]
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
CAS Number    
7173-51-5 check
3D model (JSmol)    
Interactive image
ChEMBL    
ChEMBL224987 check
ChemSpider    
22027 check
ECHA InfoCard    100.027.751 
PubChem CID    
23558
UNII    
JXN40O9Y9B check
CompTox Dashboard (EPA)    
DTXSID9032537
Properties
Chemical formula    C22H48ClN
Molar mass    362.08 g/mol
Appearance    liquid[2]
Density    0.87 g/cm3 (20 °C)[2]
Pharmacology
ATC code    D08AJ06 (WHO)
Hazards
Main hazards    corrosive[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Didecyldimethylammonium chloride (DDAC) is an antiseptic/disinfectant that is used in many biocidal applications. It causes disruption of intermolecular interactions and dissociation of lipid bilayers. It is a broad spectrum bactericidal and fungicidal 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),[3][4]. 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.

See also
Dimethyldioctadecylammonium chloride – longer di-C18 analogue

Molecular Weight of Dimethyldioctadecylammonium chloride    362.1 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Hydrogen Bond Donor Count of Dimethyldioctadecylammonium chloride    0    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Countof Dimethyldioctadecylammonium chloride    1    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count of Dimethyldioctadecylammonium chloride    18    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass of Dimethyldioctadecylammonium chloride    361.347528 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Massof Dimethyldioctadecylammonium chloride    361.347528 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Areaof Dimethyldioctadecylammonium chloride    0 Ų    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count of Dimethyldioctadecylammonium chloride    24    Computed by PubChem
Formal Charge of Dimethyldioctadecylammonium chloride    0    Computed by PubChem
Complexity of Dimethyldioctadecylammonium chloride    200    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Countof Dimethyldioctadecylammonium chloride    0    Computed by PubChem
Defined Atom Stereocenter Count  of Dimethyldioctadecylammonium chloride    0    Computed by PubChem
Undefined Atom Stereocenter Count of Dimethyldioctadecylammonium chloride    0    Computed by PubChem
Defined Bond Stereocenter Count of Dimethyldioctadecylammonium chloride    0    Computed by PubChem
Undefined Bond Stereocenter Count of Dimethyldioctadecylammonium chloride    0    Computed by PubChem
Covalently-Bonded Unit Count of Dimethyldioctadecylammonium chloride    2    Computed by PubChem
Compound of Dimethyldioctadecylammonium chloride Is Canonicalized    Yes

CAS  7173-51-5
Empirical Formula (Hill Notation):
 C22H48ClN
Molecular Weight:
 362.08
 EC Number:
 230-525-2

Didecyldimethylammonium chloride (DDAC) is used in many types of biocidal products including tableware, carpets, humidifiers, and swimming pools, etc. In spite of increased chances of Didecyldimethylammonium chlorideexposure through inhalation, studies on the inhalation toxicity of Didecyldimethylammonium chlorideare not common even though the toxicity of Didecyldimethylammonium chloridemight be significantly higher if it were to be administered through routes other than the respiratory system. Didecyldimethylammonium chloride aerosols were exposed to Sprague-Dawley rats in whole body exposure chambers for a duration of 13 weeks. The Mass Median Aerodynamic Diameters of the Didecyldimethylammonium chlorideaerosol were 0.63 μm, 0.81 μm, and 1.65 μm, and the geometric standard deviations were 1.62, 1.65, and 1.65 in the low (0.11 ± 0.06 mg/m3), the middle (0.36 ± 0.20 mg/m3) and the high (1.41 ± 0.71 mg/m3) exposure groups, respectively. Body weight was confirmed to be clearly influenced by exposure to Didecyldimethylammonium chlorideand mean body weight was approximately 35% lower in the high (1.41 ± 0.71 mg/m3) male group and 15% lower in the high (1.41 ± 0.71 mg/m3) female group compared to that of the control group. In the bronchoalveolar lavage fluid assay, the levels of albumin and lactate dehydrogenase had no effect on Didecyldimethylammonium chlorideexposure. The lung weight increased for the middle (0.36 ± 0.20 mg/m3) and the high (1.41 ± 0.71 mg/m3) concentrations of the Didecyldimethylammonium chlorideexposure group, and inflammatory cell infiltration and interstitial pneumonia were partially observed in the lungs of the middle (0.36 ± 0.20 mg/m3) and the high (1.41 ± 0.71 mg/m3) exposure groups. However, severe histopathological symptoms, including proteinosis and/or fibrosis, were not found. Based on the results of the changes in the body weight and lung weight, it is considered that the NOAEL (no-observed adverse effect) level for the 13-week exposure duration is 0.11 mg/m3.
Didecyldimethylammonium chloride (DDAC) is a representative dialkyl-quaternary ammonium biocide which is included as an active ingredient in many types of products including applications to hard surfaces (floors, tables, toilets, etc.), eating utensils, laundry detergents, carpets, agricultural tools and vehicles, ultrasonic tanks, water storage tanks, swimming pools, cooling water systems (1,2), etc. Products containing Didecyldimethylammonium chlorideare used for wood preservation and there are also registered uses for fogging agent applications in occupational settings (1). The content ratio of Didecyldimethylammonium chloridein various end-use products ranges from 0.08~80%. The residues from treated surfaces including utensils, countertops, equipment, and appliances can migrate to food and come into contact with treated and rinsed surfaces, resulting in ingestion by humans. Furthermore, not only residential handlers but also occupational handlers can suffer from exposure via the skin (2). Therefore, the main exposure pathways of Didecyldimethylammonium chloridewas assumed to be through oral or skin pathways. However, Didecyldimethylammonium chloridecan also be exposed through the respiratory system when used in aerosol form, especially for workers using the product. It has been discovered that biocides similar to Didecyldimethylammonium chloridehave been used in South Korea to sterilize household humidifiers. In South Korea, humidifiers are intensively used during the dry winter season to provide humidity. This caused prolonged exposure of Didecyldimethylammonium chloridein pregnant women, their babies, and postpartum women who were being treated in hospitals or indoor facilities became the main victims of exposure to biocides. Unfortunately, this exposure caused an unknown interstitial lung disease that was fatal in some patients (3,4).

Toxicological data on the biocides is available through many different websites (5). However, there is limited toxicological data considered to be adequate for evaluating the effects of the biocides on the human respiratory system because most patients were considered to be exposed to the biocides mainly via oral pathways or through the skin while the inhalation pathway was ignored. While there were a 13-week duration toxicity data report, a reproductive toxicity data report, and even a carcinogenicity data report available regarding Didecyldimethylammonium chloride(2,6), there were only a limited amount of reports on the inhalation toxicity. In regards to DDAC, Ohnuma et al. (1) reported that Didecyldimethylammonium chloridecould cause severe lung damage when administered through the respiratory system. The study administered 150 μg/kg of Didecyldimethylammonium chloridevia intratracheal instillation and discovered pulmonary damage in mice. A 1,500 μg/kg dose of Didecyldimethylammonium chloridecaused severe morbidity with pulmonary congestive edema. Intratracheal administering is a helpful system that helps the understanding of the lung damage caused by the particles. However, there is a chance that the toxicity could be overestimated when an excess of particles is administered at once. In our previous 2-week duration inhalation study, it was observed that only a mild inflammation was induced by 0.6 mg/m3 and 3.6 mg/m3 of Didecyldimethylammonium chlorideexposure. Fibrosis and/or proteinosis were not observed whereas the body weight of the rats significantly decreased when exposed to 3.6 mg/m3 of Didecyldimethylammonium chloride(7). In this study, we exposed rats to Didecyldimethylammonium chloridefor 13 weeks to verify if inflammation, proteinosis and/or even fibrosis might be caused by longer exposure.

Didecyldimethylammonium chloride (DDAC) is an antiseptic/disinfectant that is used in many biocidal applications. It causes disruption of intermolecular interactions and dissociation of lipid bilayers. It is a broad spectrum bactericidal and fungicidal 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.