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| | Domiphen bromide Basic information |
| | Domiphen bromide Chemical Properties |
| Melting point | 117-119 °C (lit.) | | density | 1.1411 (rough estimate) | | refractive index | 1.5570 (estimate) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | DMSO (Slightly), Methanol (Slightly), Water (Slightly) | | form | Solid | | color | White to Off-White | | Water Solubility | Soluble in ethanol, acetone, ethyl acetate, chloroform and water. Slightly soluble in benzene. | | Sensitive | Hygroscopic | | Merck | 14,3415 | | BRN | 3922742 | | Cosmetics Ingredients Functions | ANTIMICROBIAL
DEODORANT
ANTIPLAQUE
ORAL CARE | | InChI | 1S/C22H40NO.BrH/c1-4-5-6-7-8-9-10-11-12-16-19-23(2,3)20-21-24-22-17-14-13-15-18-22;/h13-15,17-18H,4-12,16,19-21H2,1-3H3;1H/q+1;/p-1 | | InChIKey | OJIYIVCMRYCWSE-UHFFFAOYSA-M | | SMILES | [Br-].CCCCCCCCCCCC[N+](C)(C)CCOc1ccccc1 | | CAS DataBase Reference | 538-71-6(CAS DataBase Reference) | | EPA Substance Registry System | 1-Dodecanaminium, N,N-dimethyl-N-(2-phenoxyethyl)-, bromide (1:1) (538-71-6) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | RIDADR | UN 2811 6.1/PG 3 | | WGK Germany | 3 | | RTECS | BQ2030000 | | TSCA | TSCA listed | | HazardClass | 6.1 | | PackingGroup | III | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 | | Hazardous Substances Data | 538-71-6(Hazardous Substances Data) |
| | Domiphen bromide Usage And Synthesis |
| Description | Domiphen is a quaternary ammonium compound and cationic surfactant with antimicrobial activity. It is active against A. viscosus, A. naeslundii, S. mutans, E. coli, and L. monocytogenes bacteria and inhibits C. neoformans yeast growth and spore germination. It also inhibits the human-ether-a-go-go-related gene (hERG) channel (IC50 = 1.5 μM in a whole-cell patch-clamp assay). Formulations containing domiphen have been used as antiseptics, disinfectants, and biocides in industrial, agricultural, veterinary, and clinical applications. | | Originator | Bradosol,Ciba,US,1958 | | Uses | Antiinfective, topical. | | Uses | Domiphen bromide is employed as a phase transfer catalyst in synthetic chemistry. It is used as a quaternary ammonium cation with cationic surfactant properties. Further, it is used as an antiseptic and an active pharmaceutical ingredient. | | Definition | ChEBI: Domiphen bromide is an aromatic ether. | | Manufacturing Process | 7 parts of β-phenoxyethyl-dimethylamine are heated for 2 hours on the boiling
water-bath with 11 parts of dodecyl bromide. A good yield of β-phenoxy-ethyldimethyl-dodecyl-ammonium bromide is obtained which, after recrystallization
from acetone, melts at 112°C. It is a white crystalline powder which dissolves
easily in water to give a neutral reaction. | | Therapeutic Function | Topical antiinfective | | Safety Profile | Poison by intraperitoneal
and intravenous routes. hfutauon data reported.
When heated to decomposiuon it emits very toxic
fumes of NOx, NH3, and Br-. See also
BROMIDES. | | References | [1] P. J. BAKER. The in vitro inhibition of microbial growth and plaque formation by surfactant drugs[J]. Journal of periodontal research, 1978, 13 5: 474-485. DOI: 10.1111/j.1600-0765.1978.tb00200.x
[2] ANNELIESE MüLLER. The Listeria monocytogenes transposon Tn6188 provides increased tolerance to various quaternary ammonium compounds and ethidium bromide[J]. Fems Microbiology Letters, 2014, 361 2: 166-173. DOI: 10.1111/1574-6968.12626
[3] SCARLETT R HOLDSWORTH Christopher J L. The major facilitator superfamily transporter MdtM contributes to the intrinsic resistance of Escherichia coli to quaternary ammonium compounds.[J]. Journal of Antimicrobial Chemotherapy, 2013, 68 4: 831-839. DOI: 10.1093/jac/dks491
[4] SéBASTIEN C ORTIZ Christina M H Mingwei Huang. Spore Germination as a Target for Antifungal Therapeutics.[J]. Antimicrobial Agents and Chemotherapy, 2019, 63 12. DOI: 10.1128/aac.00994-19
[5] MENGHANG XIA . Identification of quaternary ammonium compounds as potent inhibitors of hERG potassium channels[J]. Toxicology and applied pharmacology, 2011, 252 3: Pages 250-258. DOI: 10.1016/j.taap.2011.02.016 |
| | Domiphen bromide Preparation Products And Raw materials |
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