Triton X-100
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Triton X-100 (''n'') is a nonionic
surfactant 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 word, blend of "surface-active agent", coined in ...
that has a hydrophilic polyethylene oxide chain (on average it has 9.5 ethylene oxide units) and an aromatic
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
lipophilic Lipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...
or
hydrophobic In chemistry, hydrophobicity is the chemical property of a molecule (called a hydrophobe) that is seemingly repelled from a mass of water. In contrast, hydrophiles are attracted to water. Hydrophobic molecules tend to be nonpolar and, thu ...
group. The hydrocarbon group is a 4-( 1,1,3,3-tetramethylbutyl)- phenyl group. Triton X-100 is closely related to IGEPAL CA-630, which might differ from it mainly in having slightly shorter ethylene oxide chains. As a result, Triton X-100 is slightly more hydrophilic than Igepal CA-630 thus these two detergents may not be considered functionally interchangeable for most applications. Triton X-100 was originally a registered trademark of Rohm and Haas Co. It was subsequently purchased by Union Carbide and then acquired by Dow Chemical Company upon the acquisition of Union Carbide. Soon afterward (in 2009), Dow also acquired Rohm & Haas Co.


Physical properties

Undiluted Triton X-100 is a clear viscous fluid (less viscous than undiluted glycerol). Undiluted Triton X-100 has a
viscosity Viscosity is a measure of a fluid's rate-dependent drag (physics), resistance to a change in shape or to movement of its neighboring portions relative to one another. For liquids, it corresponds to the informal concept of ''thickness''; for e ...
of about 270 centipoise at 25 °C which comes down to about 80 centipoise at 50 °C. Triton X-100 is soluble at 25 °C in water,
toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...
, xylene, trichloroethylene, ethylene glycol,
diethyl ether Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...
,
ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
,
isopropyl alcohol Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable, organic compound with a pungent alcoholic odor. Isopropyl alcohol, an organic polar molecule, is miscible in water, ethanol, an ...
, and 1,2-dichloroethane. Triton X-100 is insoluble in kerosene, mineral spirits, and naphtha, unless a coupling agent like
oleic acid Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish due to the presence of impurities. In chemical terms, oleic acid is cl ...
is used.


Uses

Triton X-100 is a commonly used
detergent A detergent is a surfactant or a mixture of surfactants with Cleanliness, cleansing properties when in Concentration, dilute Solution (chemistry), solutions. There are a large variety of detergents. A common family is the alkylbenzene sulfonate ...
in laboratories. Triton X-100 is widely used to lyse cells to extract protein or organelles, or to permeabilize the membranes of living cells. Some applications include: * Inactivation of lipid-enveloped viruses (e.g. HIV, HBV, HCV) in manufacturing of biopharmaceuticals *Industrial purpose (plating of metal) * Ingredient in influenza vaccines, including Fluarix, Flublok, and Fluzone *Permeabilizing unfixed (or lightly fixed) eukaryotic cell membranes *Solubilizing membrane proteins in their native state in conjunction with
zwitterion In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively and negatively charged functional groups. : (1,2- dipolar compounds, such as ylides, are sometimes excluded from ...
ic detergents such as
CHAPS Chaparreras or chaps () are a type of sturdy over-pants (overalls) or leggings of Mexican origin, made of leather, without a seat, made up of two separate legs that are fastened to the waist with straps or belt. They are worn over trousers and ...
*Part of the lysis buffer (usually in a 5% solution in alkaline lysis buffer) in DNA extraction *Reducing surface tension of aqueous solutions during immunostaining (usually at a concentration of 0.1-0.5% in TBS or PBS buffer) *Dispersion of carbon materials for soft composite materials *Restricting colony expansion in ''Aspergillus nidulans'' in microbiology *Decellularization of animal-derived tissues *Removing SDS from SDS-PAGE gels prior to renaturing the proteins within the gel *Disruption of cell monolayers as a positive control for TEER measurements *Micellar catalyst *Reducing surface tension in etching such as undercutting fine features (micron size openings) in MEMS device processing *it is an ingredient in Photo-Flo, a solution used in photographic processing to prevent minerals from water being deposited on the film after drying. Apart from laboratory use, Triton X-100 can be found in several types of cleaning compounds, ranging from heavy-duty industrial products to gentle detergents. It is also a popular ingredient in homemade
vinyl record A phonograph record (also known as a gramophone record, especially in British English) or a vinyl record (for later varieties only) is an analog signal, analog sound Recording medium, storage medium in the form of a flat disc with an inscribed, ...
cleaning fluids together with distilled water and
isopropyl alcohol Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable, organic compound with a pungent alcoholic odor. Isopropyl alcohol, an organic polar molecule, is miscible in water, ethanol, an ...
.


Regulation in the European Union

In December 2012, the European Chemicals Agency (ECHA) included the substance group "4-(1,1,3,3-tetramethylbutyl)phenol, ethoxylated" – which includes Triton X-100 – in the Candidate List of substances of very high concern of the
Registration, Evaluation, Authorisation and Restriction of Chemicals Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH) is a European Union regulation dating from 18 December 2006, amended on 16 December 2008 by Regulation (EC) No 1272/2008. REACH addresses the production and use of che ...
(REACH) Regulation which addresses the production, import and use of chemical substances and their potential impacts on human health and the environment. A Triton X-100 degradation product has indeed turned out to be ecotoxic as it possesses hormone-like (estrogeno-mimetic) activity that may act on wildlife. The ECHA finally included the substance group in the Authorisation List (Annex XIV), mandating the pharmaceutical and other industries to replace this detergent by the "sunset date" January 4, 2021, thereby affecting EU manufacturers, importers, and downstream users, as well as non-European manufacturers exporting their products into the EU.


Alternatives for viral inactivation

Since the inclusion of Triton X-100 in the candidate list of substances of very high concern for authorization, pharmaceutical companies, as well as bioprocessing research groups, are in need of an alternative detergent which must at the same time be eco-friendly and effective. Ideally, a Triton X-100 replacement should generate minimal manufacturing process change, because only then the necessary updates of regulatory filings for medicines could be realized without additional animal experiments or even clinical studies. Therefore, an alternative virus-inactivating detergent should have physico-chemical properties similar to Triton X-100, be soluble, easy to remove, and eco-friendly, and not degrade to toxic metabolites. In a recent study, two alternatives for antiviral treatment in biopharmaceutical manufacturing have been identified: Triton X-100 reduced, as well as a novel compound which was named Nereid (after the mermaids in Greek mythology). As reflected by the name, Nereid can be seen as just another relative of the Triton X-100 family, however, due to a small molecular difference, it does not degrade into phenolic compounds the way that Triton X-100 does. The virus inactivation studies comprised experiments with several relevant viruses under various conditions. It turned out that at room temperature, where most virus inactivation steps in biopharmaceutical manufacturing are conducted, both Triton X-100 reduced and Nereid showed similar virus inactivating performances as Triton X-100. In contrast, for some processes that are conducted at cold temperatures, Nereid and Triton X-100 gave better results than Triton X-100 reduced.


References

{{Reflist


External links


Dow Triton X (other octylphenol ethoxylates) detergentsTriton X-100
on OpenWetWare biologists' wiki
Inactivation of Influenza Viruses by Triton X-100
Non-ionic surfactants Phenol ethers Polyethers