Benzethonium chloride

Last updated
Benzethonium chloride
Benzethonium-chloride-2D-skeletal.png
Benzethonium-chloride-3D-spacefill.png
Names
Preferred IUPAC name
N-Benzyl-N,N-dimethyl-2-{2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy}ethan-1-aminium chloride
Systematic IUPAC name
Benzyldimethyl(2-{2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy}ethyl)azanium chloride
Identifiers
3D model (JSmol)
3898548
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.073 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-479-9
KEGG
MeSH Benzethonium
PubChem CID
RTECS number
  • BO7175000
UNII
UN number 2923
  • 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 Yes check.svgY
    Key: UREZNYTWGJKWBI-UHFFFAOYSA-M Yes check.svgY
  • InChI=1/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
    Key: UREZNYTWGJKWBI-REWHXWOFAF
  • [Cl-].CC(C)(C)CC(C)(C)c1ccc(OCCOCC[N+](C)(C)Cc2ccccc2)cc1
  • [Cl-].CC(C)(C)CC(C)(C)C1=CC=C(OCCOCC[N+](C)(C)CC2=CC=CC=C2)C=C1
Properties
C27H42ClNO2
Molar mass 448.09 g·mol−1
Melting point 163 °C (325 °F; 436 K)
40 g dm−3 (at 20 °C)
Pharmacology
D08AJ08 ( WHO ) R02AA09 ( WHO )
topical
Legal status
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
Danger
H301, H314, H400
P273, P280, P305+P351+P338, P310
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Benzethonium chloride, also known as hyamine is a synthetic quaternary ammonium salt. This compound is an odorless white solid, soluble in water. It has surfactant, antiseptic, and anti-infective properties and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in cosmetics and toiletries such as soap, mouthwashes, anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride is also used in the food industry as a hard surface disinfectant. [1]

Contents

Uses

Antimicrobial

Benzethonium chloride exhibits a broad spectrum of microbiocidal activity against bacteria, fungi, mold, and viruses. Independent testing shows that benzethonium chloride is highly effective against such pathogens as methicillin-resistant Staphylococcus aureus, Salmonella , Escherichia coli , Clostridioides difficile , hepatitis B virus, hepatitis C virus, herpes simplex virus (HSV), human immunodeficiency virus (HIV), respiratory syncytial virus (RSV), and norovirus.[ citation needed ]

The US Food and Drug Administration (FDA) specifies that the safe and effective concentrations for benzethonium chloride are 0.1-0.2% in first aid products. [2] Aqueous solutions of benzethonium chloride are not absorbed through the skin. It is not approved in the US and Europe for use as a food additive. Being a quaternary ammonium salt, it is more toxic than negatively charged surfactants. [3] However, in a two-year study on rats, there was no evidence of carcinogenic activity. [4]

It is available under trade names Salanine, BZT, Diapp, Quatrachlor, Polymine D, Phemithyn, Antiseptol, Disilyn, Phermerol, and others. [5] It is also found in several grapefruit seed extract preparations [6] and can be used as a preservative, as in the anaesthetics ketamine [7] and alfaxalone. [8]

Other uses

In addition to its highly effective antimicrobial activity, benzethonium chloride contains a positively charged nitrogen atom covalently bonded to four carbon atoms. This positive charge attracts it to the skin and hair. This contributes to a soft, powdery after-feel on the skin and hair, as well as long-lasting persistent activity against micro-organisms. Also, this positively charged hydrophilic part of the molecule makes it a cationic detergent. [9]

Benzethonium chloride is also used to titrate the quantity of sodium dodecyl sulfate in a mixture of sodium dodecyl sulfate, sodium chloride and sodium sulfate, using dimidium bromide-sulphan blue as an indicator. [10]

It precipitates as turbidity with anionic polymers in aqueous solution, allowing it to be used to estimate the amount of such polymers present in a sample. This test is used in commercial and industrial water treatment, where polyacrylates, polymaleates, and sulfonated polymers are commonly employed as dispersants.[ citation needed ]

Methylbenzethonium chloride

A related compound (25155-18-4 ) is used to treat Leishmania major infections.

Regulation

Some data has suggested that long-term exposure to antibacterial ingredients could contribute to bacterial resistance or hormonal effects. Furthermore, there is little evidence that the use of such ingredients in consumer soaps is actually more effective than plain soap and water. In September 2016, the Food and Drug Administration issued a ban on nineteen consumer antiseptic wash ingredients. A ruling on benzethonium chloride, along with two other similar ingredients, was deferred for a year to allow for more data collection. [11]

Related Research Articles

A bactericide or bacteriocide, sometimes abbreviated Bcidal, is a substance which kills bacteria. Bactericides are disinfectants, antiseptics, or antibiotics. However, material surfaces can also have bactericidal properties based solely on their physical surface structure, as for example biomaterials like insect wings.

Sodium laureth sulfate (SLES), an accepted contraction of sodium lauryl ether sulfate (SLES), also called sodium alkylethersulfate, is an anionic detergent and surfactant found in many personal care products and for industrial uses. SLES is an inexpensive and very effective foaming agent. SLES, sodium lauryl sulfate (SLS), ammonium lauryl sulfate (ALS), and sodium pareth sulfate are surfactants that are used in many cosmetic products for their cleaning and emulsifying properties. It is derived from palm kernel oil or coconut oil. In herbicides, it is used as a surfactant to improve absorption of the herbicidal chemicals and reduces time the product takes to be rainfast, when enough of the herbicidal agent will be absorbed.

Sodium dodecyl sulfate (SDS) or sodium lauryl sulfate (SLS), sometimes written sodium laurilsulfate, is an organic compound with the formula CH3(CH2)11OSO3Na and structure H3C(CH2)11−O−S(=O)2−ONa+. It is an anionic surfactant used in many cleaning and hygiene products. This compound is the sodium salt of the 12-carbon organosulfate. Its hydrocarbon tail combined with a polar "headgroup" give the compound amphiphilic properties that make it useful as a detergent. SDS is also component of mixtures produced from inexpensive coconut and palm oils. SDS is a common component of many domestic cleaning, personal hygiene and cosmetic, pharmaceutical, and food products, as well as of industrial and commercial cleaning and product formulations.

<span class="mw-page-title-main">Surfactant</span> Substance that lowers the surface tension between a liquid and another material

Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word "surfactant" is a blend of surface-active agent, coined in 1950. As they consist of a water-repellent and a water-attracting part, they enable water and oil to mix; they can form foam and facilitate the detachment of dirt.

<span class="mw-page-title-main">Antibacterial soap</span> Cleaning agents containing germ-killing chemicals

Antibacterial soap is a soap which contains chemical ingredients that purportedly assist in killing bacteria. The majority of antibacterial soaps contain triclosan, though other chemical additives are also common. The effectiveness of products branded as being antibacterial has been disputed by some academics as well as the U.S. Food and Drug Administration (FDA).

<span class="mw-page-title-main">Triclosan</span> Antimicrobial agent

Triclosan is an antibacterial and antifungal agent present in some consumer products, including toothpaste, soaps, detergents, toys, and surgical cleaning treatments. It is similar in its uses and mechanism of action to triclocarban. Its efficacy as an antimicrobial agent, the risk of antimicrobial resistance, and its possible role in disrupted hormonal development remains controversial. Additional research seeks to understand its potential effects on organisms and environmental health.

<span class="mw-page-title-main">Benzalkonium chloride</span> Surfactant and antiseptic agent

Benzalkonium chloride, also known as alkyldimethylbenzylammonium chloride (ADBAC) and by the trade name Zephiran, is a type of cationic surfactant. It is an organic salt classified as a quaternary ammonium compound. ADBACs have three main categories of use: as a biocide, a cationic surfactant, and a phase transfer agent. ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-numbered alkyl chain lengths.

<span class="mw-page-title-main">Chlorhexidine</span> Disinfectant and antiseptic

Chlorhexidine is a disinfectant and antiseptic with the molecular formula C22H30Cl2N10, which is used for skin disinfection before surgery and to disinfect surgical instruments. It is also used for cleaning wounds, preventing dental plaque, treating yeast infections of the mouth, and to keep urinary catheters from blocking. It is used as a liquid or a powder. It is commonly used in salt form, either the gluconate or the acetate.

Ammonium lauryl sulfate (ALS) is the common name for ammonium dodecyl sulfate (CH3(CH2)10CH2OSO3NH4). The anion consists of a nonpolar hydrocarbon chain and a polar sulfate end group. The combination of nonpolar and polar groups confers surfactant properties to the anion: it facilitates dissolution of both polar and non-polar materials. This salt is classified as a sulfate ester. It is made from coconut or palm kernel oil for use primarily in shampoos and body-wash as a foaming agent. Lauryl sulfates are very high-foam surfactants that disrupt the surface tension of water in part by forming micelles at the surface-air interface.

<span class="mw-page-title-main">Quaternary ammonium cation</span> Polyatomic ions of the form N(–R)₄ (charge +1)

In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.

<span class="mw-page-title-main">Oligodynamic effect</span> Toxic effect of metal ions on living cells

The oligodynamic effect is a biocidal effect of metals, especially heavy metals, that occurs even in low concentrations. This effect is attributed to the antibacterial behavior of metal ions, which are absorbed by bacteria upon contact and damage their cell membranes.

A foaming agent is a material such as a surfactant or a blowing agent that facilitates the formation of foam. A surfactant, when present in small amounts, reduces surface tension of a liquid or increases its colloidal stability by inhibiting coalescence of bubbles. A blowing agent is a gas that forms the gaseous part of the foam.

<span class="mw-page-title-main">Amphiphile</span> Chemical compound with both hydrophilic and lipophilic properties

In chemistry, an amphiphile, or amphipath, is a chemical compound possessing both hydrophilic and lipophilic properties. Such a compound is called amphiphilic or amphipathic. Amphiphilic compounds include surfactants and detergents. The phospholipid amphiphiles are the major structural component of cell membranes.

<span class="mw-page-title-main">Hand sanitizer</span> Alternative to hand washing

Hand sanitizer is a liquid, gel, or foam used to kill viruses, bacteria, and other microorganisms on the hands. It can also come in the form of a cream, spray, or wipe. While hand washing with soap and water is generally preferred, hand sanitizer is a convenient alternative in settings where soap and water are unavailable. However, it is less effective against certain pathogens like norovirus and Clostridioides difficile and cannot physically remove harmful chemicals. Improper use, such as wiping off sanitizer before it dries, can also reduce its effectiveness, and some sanitizers with low alcohol concentrations are less effective. Additionally, frequent use of hand sanitizer may disrupt the skin's microbiome and cause dermatitis.

<span class="mw-page-title-main">Cetylpyridinium chloride</span> Chemical compound

Cetylpyridinium chloride (CPC) is a cationic quaternary ammonium compound used in some types of mouthwashes, toothpastes, lozenges, throat sprays, breath sprays, and nasal sprays. It is an antiseptic that kills bacteria and other microorganisms. It has been shown to be effective in preventing dental plaque and reducing gingivitis. It has also been used as an ingredient in certain pesticides. Though one study seems to indicate cetylpyridinium chloride does not cause brown tooth stains, at least one mouthwash containing CPC as an active ingredient bears the warning label "In some cases, antimicrobial rinses may cause surface staining to teeth," following a failed class-action lawsuit brought by customers whose teeth were stained.

<span class="mw-page-title-main">Organosulfate</span> Organic compounds of the form R–O–SO₃ (charge –1)

In organosulfur chemistry, organosulfates are a class of organic compounds sharing a common functional group with the structure R−O−SO−3. The SO4 core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters derived from alcohols and sulfuric acid although many are not prepared in this way. Many sulfate esters are used in detergents, and some are useful reagents. Alkyl sulfates consist of a hydrophobic hydrocarbon chain, a polar sulfate group and either a cation or amine to neutralize the sulfate group. Examples include: sodium lauryl sulfate and related potassium and ammonium salts.

Stearalkonium chloride is a type of benzalkonium chloride which is used as an anti-static agent, a surfactant and an antimicrobial. It is an ingredient in some cosmetics and hair care products, particularly conditioners. It was originally designed by the fabric industry for use as a fabric softener.

A virucide is any physical or chemical agent that deactivates or destroys viruses. The substances are not only virucidal but can be also bactericidal, fungicidal, sporicidal or tuberculocidal.

<span class="mw-page-title-main">Shampoo</span> Hair care product

Shampoo is a hair care product, typically in the form of a viscous liquid, that is used for cleaning hair. Less commonly, shampoo is available in solid bar format. Shampoo is used by applying it to wet hair, massaging the product into the scalp, and then rinsing it out. Some users may follow a shampooing with the use of hair conditioner.

A soap substitute is a natural or synthetic cleaning product used in place of soap or other detergents, typically to reduce environmental impact or health harms or provide other benefits.

References

  1. Benzethonium chloride in the Consumer Product Information Database
  2. Tentative final monograph (21CFR 333) Archived May 22, 2014, at the Wayback Machine
  3. Data Sheets
  4. National Toxicology, Program (1995). "NTP Toxicology and Carcinogenesis Studies of Benzethonium Chloride (CAS No. 121-54-0) in F344/N Rats and B6C3F1 Mice (Dermal Studies)". National Toxicology Program Technical Report Series. 438: 1–220. PMID   12595925.
  5. "Sciencelab.com, Benzethonium chloride MSDS". Archived from the original on 2018-12-06. Retrieved 2013-06-15.
  6. Takeoka, G.; Dao, L.; Wong, R. Y.; Lundin, R.; Mahoney, N. (2001). "Identification of Benzethonium Chloride in Commercial Grapefruit Seed Extracts". Journal of Agricultural and Food Chemistry. 49 (7): 3316–20. doi:10.1021/jf010222w. PMID   11453769.
  7. Coates, K. M.; Flood, P. (2001). "Ketamine and its preservative, benzethonium chloride, both inhibit human recombinant α7 and α4β2 neuronal nicotinic acetylcholine receptors in Xenopusoocytes". British Journal of Pharmacology. 134 (4): 871–9. doi:10.1038/sj.bjp.0704315. PMC   1573008 . PMID   11606328.
  8. "Alfaxan Multidose".
  9. TOXNET
  10. European Pharmacopoeia 5.0 Monographs (PDF). European Pharmacopoeia Commission. p. 2440.[ permanent dead link ]
  11. "FDA issues final rule on safety and effectiveness of antibacterial soaps". Food & Drug Administration. U.S. Food and Drug Administration. Retrieved February 7, 2017.