PRODUCTS

CETRIMONIUM BROMIDE

CAS Number: 57-09-0
EC Number: 200-311-3
IUPAC Name: N,N,N-Trimethylhexadecan-1-aminium bromide
Chemical Formula: C19H42BrN

Other names: 57-09-0, Cetrimonium bromide, Cetyltrimethylammonium bromide, Hexadecyltrimethylammonium bromide, Bromat, CETAB, Centimide, Ctmab, Cee dee, Acetoquat CTAB, Cetyl trimethyl ammonium bromide, Trimethylcetylammonium bromide, Bromuro de cetrimonio, Bromure de cetrimonium, N-Cetyltrimethylammonium bromide, Cetrimonii bromidum, Trimethylhexadecylammonium bromide, N-HEXADECYLTRIMETHYLAMMONIUM BROMIDE, Palmityltrimethyl ammonium bromide, Cetrimonio bromuro, N,N,N-Trimethylcetylammonium bromide, N,N,N-Trimethyl-1-hexadecanaminium bromide, Sumquat 6030, N-Hexadecyl-N,N,N-trimethylammonium bromide, CHEBI:3567, L64N7M9BWR, NSC-32927, DTXSID5037028, DTXCID3017028, RHODAQUAT M-242B/99, RONACARE CETRIMONIUM BROMIDE, HTAB cpd, cAtrimonium (cation), Bacteriostatic solution, D08AJ02, Dr. Zheng bacteriostatic solution, R02AA17, 200-311-3, RefChem:5660, CTAB, Hexadecyl trimethyl ammonium bromide, Cetaflon, Cetavlon, Lissolamine, Pollacid, Quamonium, Suticide, Cetarol, Micol, Cetrimide bp, Lissolamine A, Cetavlon bromide, Lissolamin V, Hexadecyltrimethylammoniumbromide, Cetrimonium (bromide), Cycloton V, Cirrasol OD, Softex KW, N,N,N-trimethylhexadecan-1-aminium bromide, (1-Hexadecyl)trimethylammonium bromide, C19H42BrN, hexadecyltrimethylazanium bromide, 1-Hexadecanaminium, N,N,N-trimethyl-, bromide, cetrimoniumbromide, MFCD00011772, Palmityltrimethylammonium bromide, cetyl trimethylammonium bromide, CHEMBL307346, Hexadecyl-trimethyl-ammonium; bromide, NCGC00164283-01, Lauroseptol, Cetrimida, Cetrimidum, hexadecyl(trimethyl)azanium;bromide, Mical, Cirrasol-OD, Bromat (VAN), hexadecyltrimethylamine, bromide, Micol (VAN), Caswell No. 167, Lissolamine V (VAN), Cetavlex, Cradocap, Zetrimid, Cetrimide [INN:BAN:JAN], Cetyltrimethylammonium (bromide);Hexadecyltrimethylammonium (bromide);CTAB, Cetrimonio bromuro [DCIT], Cetrimonium bromide [INN], CAS-57-09-0, CTABR, 347841-42-3, Cetrimonii bromidum [INN-Latin], SR-05000001830, EINECS 200-311-3, Bromure de cetrimonium [INN-French], Bromuro de cetrimonio [INN-Spanish], NSC 32927, cetyltrimethylammoniumbromide, UNII-L64N7M9BWR, EPA Pesticide Chemical Code 069117, Cetrimonium Bromide (CTAB), AI3-12209, Lissolamine V, cetyl N, Hexadecanyltrimethylammonium bromide, hexadecyl(trimethyl)azanium bromide, Cetrimonium bromide [INN:BAN:NF], hexadecyl(trimethyl)ammonium bromide, Ammonium, hexadecyltrimethyl-, bromide, Epitope ID:116869, UNII-24QSH2NL8N, EC 200-311-3, SCHEMBL4377, 24QSH2NL8N, cetyltrimethyl ammonium bromide, cetyltrimethyl-ammonium bromide, SPECTRUM1503200, Cetrimonium bromide (NF/INN), cetyl trimethyl-ammonium bromide, orb1310555, CETRIMONIUM BROMIDE [MI], HMS500K11, hexadecyl-trimethylammonium bromide, N,N-Trimethylcetylammonium bromide, HMS1922G21, HMS2092L22, HMS3652J19, HMS5082B18, Pharmakon1600-01503200, CETRIMONIUM BROMIDE [VANDF], CETRIMONIUM BROMIDE [MART.], hexadecyl(trimethyl)ammonium;bromide, hexadecyl-trimethyl ammonium bromide, HY-B1260, NSC32927, Tox21_112096, Tox21_300853, CCG-39968, CETRIMONIUM BROMIDE [USP-RS], CETRIMONIUM BROMIDE [WHO-DD], NSC758401, s4242, SBB008910, STL477543, AKOS015915119, Tox21_112096_1, CS-4893, FC13320, NSC-758401, SB40734, Hexadecyltrimethylammonium bromide, 99%, N,N-Trimethyl-1-hexadecanaminium bromide, NCGC00095012-01, NCGC00095012-02, NCGC00164283-07, NCGC00254756-01, AS-11739, BP-30064, N-Hexadecyl-N,N-trimethylammonium bromide, WLN: 16K1&1&1 &Q &E, Hexadecyltrimethylammonium bromide, >=98%, 1-Hexadecanaminium,N,N-trimethyl-, bromide, DB-050366, Hexadecyl trimethyl ammonium bromide (CTAB), H0081, NS00077218, ST51046347, SW220088-1, EN300-99610, D03454, Hexadecyltrimethylammonium bromide, AR, >=99%, A831309, Q416077, Hexadecyltrimethylammonium bromide, >=96.0% (AT), Hexadecyltrimethylammonium bromide, BioXtra, >=99%, SR-05000001830-1, SR-05000001830-3, Hexadecyltrimethylammonium bromide, analytical standard, 1-Hexadecanaminium, N,N,N-trimethyl-, bromide (1:1), Z2417556873

The closely related compounds cetrimonium chloride and cetrimonium stearate are also used as topical antiseptics and may be found in many household products such as shampoos and cosmetics.
Cetrimonium bromide, due to its relatively high cost, is typically only used in select cosmetics.

As with most surfactants, Cetrimonium bromide forms micelles in aqueous solutions.
At 303 K (30 °C) it forms micelles with aggregation number 75-120 (depending on method of determination; average ~95) and degree of ionization, α = 0.2–0.1 (fractional charge; from low to high concentration).
The binding constant (K°) of Br− counterion to a CTA+ micelle at 303 K (30 °C) is ca. 400 M-1.
This value is calculated from Br− and CTA+ ion selective electrode measurements and conductometry data by using literature data for micelle size (r = ~3 nm), extrapolated to the critical micelle concentration of 1 mM.
However, K° varies with total surfactant concentration so it is extrapolated to the point at which micelle concentration is zero.

Applications
Biological
Cell lysis is a convenient tool to isolate certain macromolecules that exist primarily inside of the cell.
Cell membranes consist of hydrophilic and lipophilic endgroups.
Therefore, detergents are often used to dissolve these membranes since they interact with both polar and nonpolar endgroups.

Cetrimonium bromide has emerged as the preferred choice for biological use because it maintains the integrity of precipitated DNA during isolation.
Cells typically have high concentrations of macromolecules, such as glycoproteins and polysaccharides, that co-precipitate with DNA during the extraction process, causing the extracted DNA to lose purity.
The positive charge of the Cetrimonium bromide molecule allows it to denature these molecules that would interfere with this isolation.

Medical
Cetrimonium bromide has been shown to have potential use as an apoptosis-promoting anticancer agent for head and neck cancer (HNC).
In vitro, Cetrimonium bromide interacted additively with γ radiation and cisplatin, two standard HNC therapeutic agents.
Cetrimonium bromide exhibited anticancer cytotoxicity against several HNC cell lines with minimal effects on normal fibroblasts, a selectivity that exploits cancer-specific metabolic aberrations.
In vivo, Cetrimonium bromide ablated tumor-forming capacity of FaDu cells and delayed growth of established tumors.
Thus, using this approach, Cetrimonium bromide was identified as a potential apoptogenic quaternary ammonium compound possessing in vitro and in vivo efficacy against HNC models.

Protein electrophoresis
Glycoproteins form broad, fuzzy bands in SDS-PAGE (Laemmli-electrophoresis) because of their broad distribution of negative charges.
Using positively charged detergents such as Cetrimonium bromide will avoid issues associated with glycoproteins.
Proteins can be blotted from Cetrimonium bromide-gels in analogy to western blots ("eastern blot"), and Myelin-associated high hydrophobic protein can be analyzed using Cetrimonium bromide 2-DE.

DNA extraction
Cetrimonium bromide serves as an important surfactant in the DNA extraction buffer system to remove membrane lipids and promote cell lysis.
Separation is also successful when the tissue contains high amounts of polysaccharides.
Cetrimonium bromide binds to the polysaccharides when the salt concentration is high, thus removing polysaccharides from solution.
A typical recipe can be to combine 100 mL of 1 M Tris HCl (pH 8.0), 280 mL 5 M NaCl, 40 mL of 0.5 M EDTA, and 20 g of Cetrimonium bromide then add double distilled water (ddH2O) to bring total volume to 1 L.

Nanoparticle synthesis
Surfactants play a key role in nanoparticle synthesis by adsorbing to the surface of the forming nanoparticle and lowering its surface energy.
Surfactants also help to prevent aggregation (e.g. via DLVO mechanisms).

Au nanoparticle synthesis
Gold (Au) nanoparticles are interesting to researchers because of their unique properties that can be used in applications such as catalysis, optics, electronics, sensing, and medicine.
Control of nanoparticle size and shape is important in order to tune its properties.
Cetrimonium bromide has been a widely used reagent to both impart stability to these nanoparticles as well as control their morphologies.
Cetrimonium bromide may play a role in controlling nanoparticle size and shape by selectively or more strongly binding to various emerging crystal facets.

Some of this control originates from the reaction of Cetrimonium bromide with other reagents in the gold nanoparticle synthesis.
For example, in aqueous gold nanoparticle syntheses, chlorauric acid (HAuCl4) may react with Cetrimonium bromide to create a CTA+-AuCl−
4 complex.
The gold complex is then reacted with ascorbic acid to produce hydrochloric acid, an ascorbic acid radical, and CTA-AuCl3.

The ascorbic acid radical and CTA-AuCl3 react spontaneously to create metallic Au0 nanoparticles and other byproducts.
An alternative or simultaneous reaction is the substitution of Cl− with Br− about the Au(III) center.
Both complexation with the ammonium cation and/or speciation of the Au(III) precursor influence the kinetics of the nanoparticle formation reaction and therefore influence the size, shape, and (size and shape) distributions of the resulting particles.

Mesoporous materials
Cetrimonium bromide is used as the template for the first report of ordered mesoporous materials.
Microporous and mesoporous inorganic solids (with pore diameters of ≤20 Å and ~20–500 Å respectively) have found great utility as catalysts and sorption media because of their large internal surface area.
Typical microporous materials are crystalline framework solids, such as zeolites, but the largest pore dimensions are still below 2 nm which greatly limit application.
Examples of mesoporous solids include silicas and modified layered materials, but these are invariably amorphous or paracrystalline, with pores that are irregularly spaced and broadly distributed in size.

There is a need to prepare highly ordered mesoporous material with good mesoscale crystallinity.
The synthesis of mesoporous solids from the calcination of aluminosilicate gels in the presence of surfactants was reported.
The material possesses regular arrays of uniform channels, the dimensions of which can be tailored (in the range of 16 Å to >100 Å) through the choice of surfactant, auxiliary chemicals, and reaction conditions.
Cetrimonium bromide was proposed that the formation of these materials takes place by means of a liquid-crystal 'templating' mechanism, in which the silicate material forms inorganic walls between ordered surfactant micelles.

Cetrimonium bromide formed micelles in the solution and these micelles further formed a two dimensional hexagonal mesostructure.
The silicon precursor began to hydrolyze between the micelles and finally filled the gap with silicon dioxide.
The template could be further removed by calcination and left a pore structure behind.
These pores mimicked exactly the structure of mesoscale soft template and led to highly ordered mesoporous silica materials.

Cetrimonium bromide is the organic bromide salt that is the bromide salt of cetyltrimethylammonium; one of the components of the topical antiseptic cetrimide.
Cetrimonium bromide has a role as a surfactant and a detergent.
Cetrimonium bromide is a quaternary ammonium salt and an organic bromide salt.
Cetrimonium bromide contains a cetyltrimethylammonium ion.

Uses
antiinfectant
Cetrimonium bromide (CTAB) is a cationic surfactant used as a template in the synthesis of Mesoporous γ-Fe2O3.
A cationic detergent used in the isolation of high molecular weight DNA.
cetrimonium bromide is a quaternary ammonium salt that can prevent the proliferation of bacteria, fungi, and yeast in cosmetic preparation, while also act as an emulsifying agent.

Purification Methods
Crystallise it from EtOH, EtOH/*benzene or from wet acetone after extracting twice with pet ether.
Shake it with anhydrous diethyl ether, filter and dissolve it in a little hot MeOH.
After cooling in the refrigerator, the precipitate is filtered off at room temperature and re-dissolved in MeOH.
Anhydrous ether is added and, after warming to obtain a clear solution, it is cooled and the crystalline material is collected.

Cetrimonium bromide and cetrimide are quaternary ammonium antiseptics, trimethylammonium derivatives, with similar structures.
Cetrimonium bromide is hexadecyltrimethylammonium.
Cetrimide is a mixture of tetradecyltrimethylammonium (mostly), dodecyl trimethyl ammonium, and hexadecyltrimethylammonium.
They dissociate in aqueous solution, forming a relatively large and complex cation, which is responsible for their surface activity, and a smaller inactive anion.
They are emulsifiers and detergents and have bactericidal activity against Gram-positive and, at higher concentrations, some Gram-negative bacteria.

What Is Cetrimonium Chloride?
Cetrimonium Chloride, is quaternary ammonium salts.
In cosmetics and personal care products, these ingredients are used in the formulation of hair conditioners, hair dyes and colors, other hair care products, and in some skin care products.

Why is Cetrimonium Chloride used in cosmetics and personal care products?
All three ingredients prevent or inhibit the buildup of static electricity.
Cetrimonium Chloride and Cetrimonium Bromide also help to cleanse the skin or to prevent odor by destroying or inhibiting the growth of microorganisms and by helping water to mix with oil and dirt so that they can be rinsed away.
They also help to form emulsions by reducing the surface tension of the substances to be emulsified and help to distribute or to suspend an insoluble solid in a liquid.

Cetrimonium Chloride and Bromide, and Steartrimonium Chloride, carry a positive charge that attracts them to the slightly negatively charged skin and hair proteins, accounting for their use as antistatics.
In addition, Cetrimonium Bromide has the ability to disrupt the surface membranes of microorganisms and has been used in antiseptics.

Roles Classification
Chemical Role(s):
surfactant
A substance which lowers the surface tension of the medium in which it is dissolved, and/or the interfacial tension with other phases, and, accordingly, is positively adsorbed at the liquid/vapour and/or at other interfaces.
detergent
A surfactant (or a mixture containing one or more surfactants) having cleaning properties in dilute solutions.

Application(s):
detergent
A surfactant (or a mixture containing one or more surfactants) having cleaning properties in dilute solutions.

CETRIMONIUM BROMIDE is a cationic detergent suitable for the isolation of high molecular weight DNA in plants and other organisms.

Cetrimonium bromide (CTAB) is an amine based cationic quaternary surfactant, is one of the components of the topical antiseptic Cetrimide.

An emulsifier and surfactant
Cetrimonium bromide (CTAB) allows the oil and dirt trapped in hair to be rinsed away, leaving it clean.
Cetrimonium bromide (CTAB) also helps the hair lie flat, giving it silky shine and prevents static build-up which causes flyaway hair.
An ammonium salt, emulsifier and a surface-active agent (surfactant).
All surfactants are partly water-soluble and partly oil-soluble.
Cetrimonium bromide (CTAB)'s this quality that allows oil and water to mix.
When used in cosmetic products, the surfactant molecules become organized in a structure that can trap oil-based dirt.

Cetrimonium bromide (CTAB) is a quaternary ammonium compound.
Cetrimonium bromide (CTAB) was first introduced as a combined cleanser and skin antiseptic by Barnes (1942).
Cetrimonium bromide (CTAB) combines excellent detergent properties and minimal toxicity with a useful antiseptic action.

Cetrimonium bromide (CTAB) affects membrane permeability allowing ‘leaking’ of essential cell constituents leading to cell death.
This medication is a skin antiseptic and disinfectant prescribed for seborrhoeic dermatitis and wound cleansing.
The cream has a bactericidal activity against gram-positive bacteria and incompatible with soaps and other anionic surfactants.

Application Notes
Cetrimonium bromide (CTAB) ia used as an cationic surfactant suitable for the isolation of high molecular weight DNA in plants and other organisms(by a rapid method) as well as plant DNA for use in PCR analysis.
Cetrimonium bromide (CTAB) has been used to precipitate nucleic acids.
Cetrimonium bromide (CTAB) provides enhancement of Concanavalin A mediated agglutination.
Cetrimonium bromide (CTAB) has been used for the determination of protein molecular weights in electrophoretic systems and for determination of critical micelle concentration of detergents.
Cetrimonium bromide (CTAB) has also been used as a titrant for potentiometric titration of perchlorate and as a phase-transfer catalyst in reduction of arenes and heterocyclic compounds.

Usage Statement
Unless specified otherwise, MP Biomedical's products are for research or further manufacturing use only, not for direct human use.
For more information, please contact our customer service department.

Cetrimonium Bromide is a known component of the broad-spectrum antiseptic cetrimide, which is a mixture of different quaternary ammonium salts.
Cetrimonium bromide is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 to < 100 tonnes per annum.
Cetrimonium bromide is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Consumer Uses
Cetrimonium bromide is used in the following products: cosmetics and personal care products, perfumes and fragrances and pharmaceuticals. Other release to the environment of Cetrimonium bromide is likely to occur from: indoor use as processing aid and outdoor use as processing aid.

Widespread uses by professional workers
Cetrimonium bromide is used in the following products: laboratory chemicals, pH regulators and water treatment products and cosmetics and personal care products.
Cetrimonium bromide is used in the following areas: health services and scientific research and development.
Other release to the environment of Cetrimonium bromide is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).

Cetrimonium bromide is used in the following products: perfumes and fragrances, pharmaceuticals, cosmetics and personal care products, laboratory chemicals and water treatment chemicals.
Release to the environment of Cetrimonium bromide can occur from industrial use: formulation of mixtures and formulation in materials.

Cetrimonium bromide is used in the following products: laboratory chemicals, pH regulators and water treatment products and cosmetics and personal care products.
Cetrimonium bromide is used in the following areas: scientific research and development and health services.
Cetrimonium bromide is used for the manufacture of: chemicals.

Release to the environment of Cetrimonium bromide can occur from industrial use: in processing aids at industrial sites, as processing aid and as an intermediate step in further manufacturing of another substance (use of intermediates).
Manufacture
Release to the environment of Cetrimonium bromide can occur from industrial use: manufacturing of the substance.

Cetrimonium bromide is an amine based cationic quaternary surfactant, is one of the components of the topical antiseptic Cetrimide.

Cetrimonium bromide is one of the components of the topical antiseptic cetrimide.
The cetrimonium (hexadecyltrimethylammonium) cation is an effective antiseptic agent against bacteria and fungi.
Cetrimonium bromide is also one of the main components of the buffer for the extraction of DNA.
Cetrimonium bromide has been widely used in synthesis of gold nanoparticles (e.g., spheres, rods, bipyramids), mesoporous silica nanoparticles (e.g., MCM-41), and hair conditioning products.
The closely related compounds cetrimonium chloride and cetrimonium stearate are also used as topical antiseptics and may be found in many household products such as shampoos and cosmetics.
Cetrimonium bromide , due to its relatively high cost, is typically only used in select cosmetics.

Cetyltrimethylammonium Bromide is also referred to as Cetrimonium bromide and is a cationic surfactant that is used as a buffer solution during the extraction of DNA, in hair conditioning products, as well as, in the synthesis of gold nanoparticles.

Description
A quaternary ammonium salt.
Cetrimonium bromide, or cetrimonium bromide, is used as a Cationic detergent, Surfactant, and Bactericide.
Cetrimonium bromide has been added to glue-paste formulations as a nontoxic alternative to Phenol (Ackroyd 1996).

Cetrimonium bromide is a cationic detergent, soluble in H2O and readily soluble in alcohol.
Cetrimonium bromide is commonly used in the preparation and purification of genomic DNA from bacteria including DNA mini preps for sequencing.
Cetrimonium bromide complexes with both polysaccharide and residual protein.

General Description
Cationic detergent suitable for the isolation of high molecular weight DNA in plants and other organisms.