Dodecyltrimethylammonium Chloride

  • CAT Number: R010890
  • CAS Number: 112-00-5
  • Molecular Formula: C15H34ClN
  • Molecular Weight: 263.894
  • Purity: ≥95%
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Dodecyltrimethylammonium chloride(CAS: 112-00-5) is a quaternary ammonium compound (QAC) commonly used as a cationic surfactant. It is used in antimicrobial sanitizers due to its surface activity and germicidal efficiency.

Catalog Number R010890
CAS Number 112-00-5
Molecular Formula

C15H34ClN

Purity 95%
Storage Store at 4°C
IUPAC Name dodecyl(trimethyl)azanium;chloride
InChI InChI=1S/C15H34N.ClH/c1-5-6-7-8-9-10-11-12-13-14-15-16(2,3)4;/h5-15H2,1-4H3;1H/q+1;/p-1
InChIKey DDXLVDQZPFLQMZ-UHFFFAOYSA-M
SMILES CCCCCCCCCCCC[N+](C)(C)C.[Cl-]
Reference

[1]. Sci Total Environ. 2016 Aug 1;560-561:197-203. doi: 10.1016/j.scitotenv.2016.03.235. Epub 2016 Apr 19.<br />
Sorption of dodecyltrimethylammonium chloride (DTAC) to agricultural soils.<br />
Xiang L(1), Sun TF(1), Zheng MJ(1), Li YW(1), Li H(1), Wong MH(2), Cai QY(3), Mo CH(4).<br />
Author information: (1)Guangdong Provincial Research Center for Environment Pollution Control and Remediation Materials, School of Environment, Jinan University, Guangzhou 510632, China. (2)Guangdong Provincial Research Center for Environment Pollution Control and Remediation Materials, School of Environment, Jinan University, Guangzhou 510632, China; Consortium on Health, Environment, Education and Research (CHEER), Department of Science and Environmental Studies, Institute of Education, Tai Po, Hong Kong, China. (3)Guangdong Provincial Research Center for Environment Pollution Control and Remediation Materials, School of Environment, Jinan University, Guangzhou 510632, China. Electronic address: [email protected]. (4)Guangdong Provincial Research Center for Environment Pollution Control and Remediation Materials, School of Environment, Jinan University, Guangzhou 510632, China. Electronic address: [email protected].<br />
Quaternary ammonium compounds (QACs) used as cationic surfactants are intensively released into environment to be pollutants receiving more and more concerns. Sorption of dodecyltrimethylammonium chloride (DTAC), one of commonly used alkyl QACs, to five types of agricultural soils at low concentrations (1-50mg/L) was investigated using batch experiments. DTAC sorption followed pseudo-second-order kinetics and reached reaction equilibrium within 120min. Both Freundlich model and Langmuir model fitted well with DTAC isotherm data with the latter better. DTAC sorption was spontaneous and favorable, presenting a physical sorption dominated by ion exchanges. Sorption distribution coefficient and sorption affinity demonstrated that soil clay contents acted as a predominant phase of DTAC sorption. DTAC could display a higher mobility and potential accumulation in crops in the soils with lower clay contents and lower pH values. Sorption of DTAC was heavily affected by ions in solution with anion promotion and cation inhibition.<br />
DOI: 10.1016/j.scitotenv.2016.03.235 PMID: 27101455 [Indexed for MEDLINE]<br />
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[2]. Appl Environ Microbiol. 2013 Apr;79(7):2371-6. doi: 10.1128/AEM.03228-12. Epub 2013 Feb 1.<br />
Pathogenicity of dodecyltrimethylammonium chloride-resistant Salmonella enterica.<br />
Kautz MJ(1), Dvorzhinskiy A, Frye JG, Stevenson N, Herson DS.<br />
Author information: (1)Department of Biological Sciences, University of Delaware, Newark, Delaware, USA.<br />
Salmonella infection causes a self-limiting gastroenteritis in humans but can also result in a life-threatening invasive disease, especially in old, young, and/or immunocompromised patients. The prevalence of antimicrobial and multidrug-resistant Salmonella has increased worldwide since the 1980s. However, the impact of antimicrobial resistance on the pathogenicity of Salmonella strains is not well described. In our study, a microarray was used to screen for differences in gene expression between a parental strain and a strain of Salmonella enterica serovar Enteritidis with reduced susceptibility (SRS) to the widely used antimicrobial sanitizer dodecyltrimethylammonium chloride (DTAC). Three of the genes, associated with adhesion, invasion, and intracellular growth (fimA, csgG, and spvR), that showed differences in gene expression of 2-fold or greater were chosen for further study. Real-time reverse transcriptase PCR (real-time RT-PCR) was used to confirm the microarray data and to compare the expression levels of these genes in the parental strain and four independently derived SRS strains. All SRS strains showed lower levels of gene expression of fimA and csgG than those of the parental strain. Three of the four SRS strains showed lower levels of spvR gene expression while one SRS strain showed higher levels of spvR gene expression than those of the parental strain. Transmission electron microscopy determined that fimbriae were absent in the four SRS strains but copiously present in the parental strain. All four SRS strains demonstrated a significantly reduced ability to invade tissue culture cells compared to the parental strains, suggesting reduced pathogenicity of the SRS strains.<br />
DOI: 10.1128/AEM.03228-12 PMCID: PMC3623252 PMID: 23377943 [Indexed for MEDLINE]<br />
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[3]. Phys Rev E. 2020 Sep;102(3-1):032401. doi: 10.1103/PhysRevE.102.032401.<br />
Dodecyltrimethylammonium bromide surfactant effects on DNA: Unraveling the competition between electrostatic and hydrophobic interactions.<br />
Silva EF(1), Andrade UMS(2), de Oliveira KM(3), Teixeira AVNC(3), Rocha MS(3).<br />
Author information: (1)Departamento de F&iacute;sica, Universidade Federal de Vi&ccedil;osa, Vi&ccedil;osa, Minas Gerais, 36570-900, Brazil and Departamento de F&iacute;sica, Universidade Federal de Juiz de Fora, Juiz de Fora, Minas Gerais, 36036-900, Brazil. (2)Departamento de F&iacute;sica, Universidade Federal de Vi&ccedil;osa, Vi&ccedil;osa, Minas Gerais, 36570-900, Brazil and Departamento de Forma&ccedil;&atilde;o Geral, Centro Federal de Educa&ccedil;&atilde;o Tecnol&oacute;gica de Minas Gerais, Curvelo, Minas Gerais, 35790-000, Brasil. (3)Departamento de F&iacute;sica, Universidade Federal de Vi&ccedil;osa, Vi&ccedil;osa, Minas Gerais, 36570-900, Brazil.<br />
We present a new study on the interaction of the DNA molecule with the surfactant dodecyltrimethylammonium bromide (DTAB), performed mainly with optical tweezers. Single-molecule force spectroscopy experiments performed in the low-force entropic regime allowed a robust characterization of the DNA-DTAB interaction, unveiling how the surfactant changes the mechanical properties of the biopolymer, the binding parameters, and the competition of the two mechanisms involved in the interaction: electrostatic attraction between the cationic surfactant heads and the negative phosphate backbone of the DNA and hydrophobic interactions between the tails of the bound DTAB molecules, which can result in DNA compaction in solution depending on the quantity of bound surfactant. Finally, force clamp experiments with magnetic tweezers and gel electrophoresis assays confirm that DTAB compacts DNA depending not only on the surfactant concentration but also on the conformation of the biopolymer in solution. The present study provides new insights on general aspects of the DNA-surfactant complexes formation, contributing to the fundamental knowledge of the physics of such interactions.<br />
DOI: 10.1103/PhysRevE.102.032401 PMID: 33076016 [Indexed for MEDLINE]<br />
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[4]. J Colloid Interface Sci. 2008 May 15;321(2):442-51. doi: 10.1016/j.jcis.2008.02.030. Epub 2008 Mar 4.<br />
Micellar behavior of aqueous solutions of dodecyldimethylethylammonium bromide, dodecyltrimethylammonium chloride and tetradecyltrimethylammonium chloride in the presence of alpha-, beta-, HPbeta- and gamma-cyclodextrins.<br />
Mehta SK(1), Bhasin KK, Dham S, Singla ML.<br />
Author information: (1)Department of Chemistry, Panjab University, Chandigarh-160 014, India. [email protected]<br />
Conductivity, static fluorescence and (1)H NMR measurements have been carried out to study the micellar behavior of aqueous solutions of dodecyldimethylethylammonium bromide (DDAB), dodecyltrimethylammonium chloride (DTAC) and tetradecyltrimethylammonium chloride (TDAC) in absence and presence of alpha-cyclodextrin (alpha-CD), beta-cyclodextrin (beta-CD), hydroxypropyl-beta-cyclodextrin (HPbeta-CD) and gamma-cyclodextrin (gamma-CD). The conductivity measurements were carried out at 298.15 K. The influence of cyclodextrins on the micellar parameters, such as cmc* (apparent critical micellar concentration), beta (degree of ionization) have been analyzed. Thermodynamics of the systems was discussed in terms of the change in standard free energy of micellization, DeltaG(m)(0). Micellization was found to be less spontaneous in presence of cyclodextrins. The fluorescence intensity of the surfactant solutions is enhanced by the addition of cyclodextrins. The association constants obtained from conductivity and fluorescence data suggest the binding of gamma-CD with the surfactants to be strongest among all the cyclodextrins used. (1)H NMR chemical shift changes provide powerful means for probing the cyclodextrin-micellar interactions and inclusion of surfactant is shown by the change in the chemical shift of some of the guest and host protons in comparison with the chemical shifts of the same protons in the free compounds.<br />
DOI: 10.1016/j.jcis.2008.02.030 PMID: 18342875<br />
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[5]. Biofouling. 2021 Jan;37(1):49-60. doi: 10.1080/08927014.2021.1873958. Epub 2021 Jan 31.<br />
Anti-biofilm activity of dodecyltrimethylammonium chloride microcapsules against Salmonella enterica serovar Enteritidis and Staphylococcus aureus.<br />
Khelissa S(1), Gharsallaoui A(2), Wang J(2), Dumas E(2), Barras A(3), Jama C(1), Jbilou F(4), Loukili N(5), Chihib NE(1).<br />
Author information: (1)Univ Lille, CNRS, INRAE, Centrale Lille, UMR 8207 – UMET – Unit&eacute; Mat&eacute;riaux et Transformations, Lille, France. (2)Univ Lyon, Universit&eacute; Claude Bernard Lyon 1, CNRS, LAGEPP UMR 5007, Villeurbanne, France. (3)Univ Lille, CNRS, Centrale Lille Univ. Polytechnique Hauts-de-France, UMR 8520-IEMN, Lille, France. (4)Former student of the University of Lille, Lille, France. (5)Infection Control Unit, Centre Hospitalier Universitaire de Lille, Lille, France.<br />
Dodecyltrimethylammonium chloride (DTAC) was trapped into maltodextrins/pectin spray dried microcapsules to improve its activity against Salmonella enteritidis and Staphylococcus aureus biofilms. Two different microcapsules were prepared: uncomplexed DTAC-microcapsules (UDM), containing DTAC and maltodextrins; and complexed DTAC-microcapsules (CDM) containing DTAC complexed with pectin and maltodextrins. The minimum inhibitory concentrations (MIC) of both free and microencapsulated DTAC were investigated against S. Enteritidis and S. aureus. The MICs of DTAC were significantly lower when encapsulated. CDM treatment resulted in a 2 and 3.2 log reduction in S. aureus and S. Enteritidis biofilm culturable biomass, respectively. Microencapsulation reduced the cytotoxicity of DTAC by up to 32-fold. Free DTAC and CDM targeted the cell membrane resulting in the leakage of the intracellular molecules and subsequent cell death. The development of DTAC microcapsules reduced the amount of DTAC required to maintain the high standards of cleanliness and hygiene required in the food processing industries.<br />
DOI: 10.1080/08927014.2021.1873958 PMID: 33522301 [Indexed for MEDLINE]

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