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
CAS Number	7173-51-5  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL224987  Y
ChemSpider	22027  Y
ECHA InfoCard	100.027.751
PubChem CID	23558
UNII	JXN40O9Y9B  Y
CompTox Dashboard (EPA)	DTXSID9032537
InChI 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 Y Key: RUPBZQFQVRMKDG-UHFFFAOYSA-M Y 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
SMILES [Cl-].C(CCCCC[N+](C)(CCCCCCCCCC)C)CCCC
Properties
Chemical formula	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
ATC code	D08AJ06 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	toxic
GHS labelling:
Pictograms
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y  verify  (what is  YN ?) Infobox references

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

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). ^{[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

• Dimethyldioctadecylammonium chloride – longer di-C18 analogue

References

1. "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. 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.
4. 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.
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.