Cetalkonium chloride
Product Information
Molecular Formula
C25H46ClN
Molecular Weight
396.09
Description
Cetalkonium chloride is a quaternary ammonium compound and cationic surfactant used as an antiseptic, preservative, and antimicrobial agent. It interacts with negative charges on bacterial cell membranes, disrupting membrane integrity and causing cell death. The compound exhibits broad-spectrum antibacterial activity against Gram-positive and Gram-negative bacteria including MRSA, E. coli, A. baumannii, K. pneumoniae, and E. faecium, with MICs ranging from 1.0 μg/mL to 126.0 μM. It also shows antibiofilm properties and antiviral activity against Lassa, Marburg, and Ebola viruses. Cetalkonium chloride is FDA-approved for use in over-the-counter topical products as a skin protectant, and is found in formulations for mouth, throat, and eye infections (e.g., Bonjela mouth ulcer gel). It also serves as an excipient in ocular drug delivery systems, improving precorneal residence time and bioavailability.
Synonyms
Benzenemethanaminium, N-hexadecyl-N,N-dimethyl-, chloride (1:1); Benzylhexadecyldimethylammonium chloride; Ammonyx G; Benzylcetyldimethylammonium chloride; Cetol; Cetyldimethylbenzylammonium chloride; Cetylon; Cetyl zephiran; Dimethylbenzylhexadecylammonium chloride; N-Hexadecyl-N-benzyl-N,N-dimethylammonium chloride; Hexadecyldimethylbenzylammonium chloride; n-Hexadecyldimethylbenzylammonium chloride; Pharycidin Concentrate; Tetraseptan; Zettyn chloride; Hexadecylbenzyldimethylammonium chloride; Dimethylbenzylcetylammonium chloride; Acinol; Ammonyx T; Cetylbenzyldimethylammonium chloride; Benzyldimethylhexadecylammonium chloride; DMCBAC; Dehyquart CBB; N-Benzyl-N-cetyldimethylammonium chloride; Baktonium; Win 357; Banicol; Benzaletas; Bicetonium; Bonjela; Spilan; Dehyquart CDB; CDBAC; Benzyldimethylcetylammonium chloride; Querton 16BCL; Sanisol C; Acquat CDAC; Acetoquate CDAC; Zettyn; N-Hexadecyl-N,N-dimethyl-N-benzylammonium chloride; Benzyl-n-hexadecyldimethylammonium chloride; HBAC; N-Benzyl-N,N-dimethyl-N-hexadecylammonium chloride; (Hexadecyl)(dimethyl)(benzyl)amonium chloride
IUPAC Name
benzyl-hexadecyl-dimethylazanium;chloride
SMILES
CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1.[Cl-]
InChI
InChI=1S/C25H46N.ClH/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-20-23-26(2,3)24-25-21-18-17-19-22-25/h17-19,21-22H,4-16,20,23-24H2,1-3H31H/q+1/p-1
InChI Key
SXPWTBGAZSPLHA-UHFFFAOYSA-M
Melting Point
54-56 °C
Purity
>97.0% by HPLC
Solubility
Soluble in DMSO
Appearance
White to milky white powder
Application
A quaternary surfactant used as a germicide/fungicide in leather processing, textile dyeing, and silicone-based water repellents.
Storage
Store at RT
Related CAS
10328-34-4 (free base)
Safety Information
Hazards
H315:
Causes skin irritation.
H319:
Causes serious eye irritation.
Causes skin irritation.
H319:
Causes serious eye irritation.
Precautionary Statement
P264:
Wash thoroughly after handling.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:
IF ON SKIN:
Wash with plenty of soap and water.
P332+P313:
If skin irritation occurs:
Get medical advice/attention.
P337+P313:
If eye irritation persists:
Get medical advice/attention.
P362+P364:
Take off contaminated clothing. [As modified by IV ATP].
And wash it before reuse. [Added by IV ATP].
Wash thoroughly after handling.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:
IF ON SKIN:
Wash with plenty of soap and water.
P332+P313:
If skin irritation occurs:
Get medical advice/attention.
P337+P313:
If eye irritation persists:
Get medical advice/attention.
P362+P364:
Take off contaminated clothing. [As modified by IV ATP].
And wash it before reuse. [Added by IV ATP].
Computed Properties
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
17
Exact Mass
395.3318782 g/mol
Monoisotopic Mass
395.3318782 g/mol
Topological Polar Surface Area
0Ų
Heavy Atom Count
27
Formal Charge
0
Complexity
291
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
2
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-114027299-A | Atomizing and refreshing bactericide for internal circulation space of air conditioner and preparation method of bactericide | 2021-12-09 |
| CN-114083865-A | Polyester film for five-layer dry film resist and preparation method thereof | 2021-12-04 |
| CN-113981570-A | Method for recovering white oil in production process of ultra-high molecular weight polyethylene fiber | 2021-11-12 |
| CN-114106811-A | Two-dimensional nano material reinforced clean fracturing fluid and preparation method and application thereof | 2021-11-10 |
| CN-113981221-A | Zirconium-hafnium separation extracting agent, application thereof and zirconium-hafnium separation method | 2021-10-28 |
| CN-114149874-A | Aerosol detergent based on ionic liquid and preparation method thereof | 2021-10-19 |
| CN-114097785-A | Polysaccharide-based photothermal sterilization material and application thereof in seed protection and grain storage | 2021-10-18 |
| DE-102021124147-A1 | Synthetic resin material and method for producing a milling blank for medical-technical molded parts | 2021-09-17 |
| CN-113984912-A | Method for detecting benzalkonium chloride in disinfection product | 2021-09-02 |
| CN-113813287-A | Preparation method of compound medicinal liquid for treating verruca vulgaris | 2021-08-27 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 28551711 | 2017-12-01 | Why are most phospholipidosis inducers also hERG blockers? | Archives of toxicology |
| 24001405 | 2014-04-01 | Benefits of cetalkonium chloride cationic oil-in-water nanoemulsions for topical ophthalmic drug delivery | The Journal of pharmacy and pharmacology |
| 22539315 | 2012-04-01 | Cationic detergents enable the separation of membrane proteins of Plasmodium falciparum-infected erythrocytes by 2D gel electrophoresis | Electrophoresis |
| 21594238 | 2011-06-28 | A nano-confined charged layer defies the principle of electrostatic interaction | Chemical communications (Cambridge, England) |
| 21111625 | 2011-01-01 | Synthesis and antibacterial activity study of a novel class of cationic anthraquinone analogs | Bioorganic & medicinal chemistry |
| 19153686 | 2009-01-01 | 16-BAC/SDS-PAGE analysis of membrane proteins of yeast mitochondria purified by free flow electrophoresis | Methods in molecular biology (Clifton, N.J.) |
| 19153699 | 2009-01-01 | Two-dimensional separation of membrane proteins by 16-BAC-SDS-PAGE | Methods in molecular biology (Clifton, N.J.) |
| 18975855 | 2008-11-01 | Effects of preparation and experimental conditions on removal of phenol by surfactant-modified zeolites | Environmental technology |
| 18347566 | 2008-01-31 | Reduction of quaternary ammonium-induced ocular surface toxicity by emulsions: an in vivo study in rabbits | Molecular vision |
| 17221235 | 2007-10-01 | Evaluation of two proteomics technologies used to screen the membrane proteomes of wild-type Corynebacterium glutamicum and an L-lysine-producing strain | Analytical and bioanalytical chemistry |
