Benzethonium Chloride
Product Information
Molecular Formula
C27H42NO2.Cl
Molecular Weight
448.08
Description
Benzethonium Chloride is a synthetic quaternary ammonium salt with antimicrobial and surfactant properties. It is commonly used as an antimicrobial agent in cosmetics and disinfectants. It also acts as a potent nAChR inhibitor with IC50 of 49 nM and 122 nM for α4β2 nAChRs and α7 nAChRs, respectively.
Synonyms
Phemeride; Quatrachlor; Hyamine
IUPAC Name
benzyl-dimethyl-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethyl]azaniumchloride
SMILES
CC(C)(C)CC(C)(C)C1=CC=C(C=C1)OCCOCC[N+](C)(C)CC2=CC=CC=C2.[Cl-]
InChI
InChI=1S/C27H42NO2.ClH/c1-26(2,3)22-27(4,5)24-13-15-25(16-14-24)30-20-19-29-18-17-28(6,7)21-23-11-9-8-10-12-23;/h8-16H,17-22H2,1-7H3;1H/q+1;/p-1
InChI Key
UREZNYTWGJKWBI-UHFFFAOYSA-M
Melting Point
160-162°C
Purity
>98%
Density
0.998 g/mL at 20°C
Solubility
1-5 g/100 mL at 18 °C
Appearance
White Solid
Application
Used as a cationic detergent, germicide for cleansing food and dairy utensils, swimming pool algaecide, dandruff-control agent, deodorant, topical antiseptic, spermicide, and astringent; Used as a preservative in cosmetics and pharmaceuticals and as a reagent for determining protein in cerebrospinal fluid.
Storage
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture.
Refractive Index
1.5101 at 25 °C
Stability
Stability Stable, but hygroscopic. Incompatible with strong oxidizing agents, soap, anionic detergents, nitrates, acids. Light sensitive.
LogP
3.07640
Decomposition
When heated to decomposition it emits very toxic fumes of /hydrogen choride and nitrogen oxides.
Odor
MILD ODOR
Safety Information
Hazards
H302:
Harmful if swallowed.
H315:
Causes skin irritation.
H319:
Causes serious eye irritation.
Harmful if swallowed.
H315:
Causes skin irritation.
H319:
Causes serious eye irritation.
Precautionary Statement
P264:
Wash thoroughly after handling.
P270:
Do not eat, drink or smoke when using this product.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312+P330:
IF SWALLOWED:
Call a POISON CENTER or doctor/physician if you feel unwell.
Rinse mouth.
P337+P313:
If eye irritation persists:
Get medical advice/attention.
P501:
Dispose of contents/container in accordance with local/regional/national/international regulations.
Wash thoroughly after handling.
P270:
Do not eat, drink or smoke when using this product.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312+P330:
IF SWALLOWED:
Call a POISON CENTER or doctor/physician if you feel unwell.
Rinse mouth.
P337+P313:
If eye irritation persists:
Get medical advice/attention.
P501:
Dispose of contents/container in accordance with local/regional/national/international regulations.
Computed Properties
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
12
Exact Mass
447.2904073 g/mol
Monoisotopic Mass
447.2904073 g/mol
Topological Polar Surface Area
18.5Ų
Heavy Atom Count
31
Formal Charge
0
Complexity
466
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 |
|---|---|---|
| EP-3818972-A2 | Piroctone olamine granules for use in cosmetic compositions | 2021-01-29 |
| US-10882852-B1 | 3-vinylquinolines as cancer cells inhibitors | 2020-07-09 |
| WO-2021053651-A1 | Extract of cocculus hirsutus for treatment of covid-19 | 2020-04-27 |
| US-11021531-B1 | Anti-SARS-Cov-2 antibodies derived from 2GHW | 2020-03-23 |
| US-11021532-B1 | Superhuman anti-SARS-CoV-2 antibodies and uses thereof | 2020-03-23 |
| US-11028150-B1 | Anti-SARS-CoV-2 antibodies derived from 2DD8 | 2020-03-23 |
| US-11028167-B1 | Anti-SARS-Cov-2 antibodies derived from 3bgf | 2020-03-23 |
| US-11034762-B1 | Anti-SARS-Cov-2 antibodies derived from CR3022 | 2020-03-23 |
| US-10980756-B1 | Methods of treatment | 2020-03-16 |
| EP-3677244-A2 | Compositions comprising multilamellar vesicles | 2020-02-04 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 34592322 | 2021-11-15 | Proarrhythmic effects induced by benzethonium chloride and domiphen bromide in vitro and in vivo | Toxicology and applied pharmacology |
| 32094294 | 2020-05-01 | Pharmacological Characterization of the Novel and Selective α7 Nicotinic Acetylcholine Receptor-Positive Allosteric Modulator BNC375 | The Journal of pharmacology and experimental therapeutics |
| 29514330 | 2018-06-01 | Effects of Consumer Antimicrobials Benzalkonium Chloride, Benzethonium Chloride, and Chloroxylenol on Colonic Inflammation and Colitis-Associated Colon Tumorigenesis in Mice | Toxicological sciences : an official journal of the Society of Toxicology |
| 29594315 | 2018-06-01 | Profiling the immunotoxicity of chemicals based on in vitro evaluation by a combination of the Multi-ImmunoTox assay and the IL-8 Luc assay | Archives of toxicology |
| 24052561 | 2013-12-01 | Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model | Toxicological sciences : an official journal of the Society of Toxicology |
| 23792315 | 2013-08-01 | Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride | European journal of medicinal chemistry |
| 23571415 | 2013-06-01 | Structure-based identification of OATP1B1/3 inhibitors | Molecular pharmacology |
| 23313619 | 2013-03-01 | Mechanism of HERG potassium channel inhibition by tetra-n-octylammonium bromide and benzethonium chloride | Toxicology and applied pharmacology |
| 22142417 | 2012-08-01 | Visual and confocal microscopic interpretation of patch tests to benzethonium chloride and benzalkonium chloride | Skin research and technology : official journal of International Society for Bioengineering and the Skin (ISBS) [and] International Society for Digital Imaging of Skin (ISDIS) [and] International Society for Skin Imaging (ISSI) |
| 21387348 | 2012-07-01 | Comparative study on toxic effects induced by oral or intravascular administration of commonly used disinfectants and surfactants in rats | Journal of applied toxicology : JAT |
