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TRITON X-100

Synonyms: TRITON X-100; 2315-67-5; Octoxynol-1; 9002-93-1; Hydrol SW; Triton X;  Alfenol 3; Marlophen 820; Neutronyx 605; Octoxinolum; Poletoxol; Conco nix-100

TRITON X-100 is a nonionic surfactant that has a hydrophilic polyethylene oxide chain and an aromatic hydrocarbon lipophilic or hydrophobic group. 

Synonyms:
TRITON X-100; TRİTON X-100; Triton™-X ; Triton X-100; 2315-67-5; Octoxynol-1; Octoxinol; 9002-93-1; Octoxynol; Octoxynol-3; Triton X; Preceptin; Triton x-45; Triton X 45; Octoxynol-9; Hydrol SW; Triton X 100; Triton X 305; Alfenol 3; Alfenol 9; Marlophen 820; Neutronyx 605; Octoxinolum; Poletoxol; Conco nix-100; Hyonic pe-250; Triton X 35; Antarox A-200; Ortho-gynol; Igepal CA-630; Triton X 165; Triton X 405; Triton X 705; Triton X-102; Octoxynol-11; Octoxynol-12; Octoxynol-25; Octoxynol-33; Octoxynol-40; Peg 4-isooctylphenyl ether; PEG-9 Octyl phenyl ether; 4-tert-Octylphenyl peg ether; Peg 4-tert-octylphenyl ether; Texofor FP 300; Triton X 101; Triton X 102; Ethanol, 2-[4-(1,1,3,3 tetramethylbutyl) phenoxy]-; OPE 30; 4-tert-Octylphenol; Monoethoxylate; Polyoxyethylene octyl phenyl ether; Octoxinolum [INN-Latin]; Octoxynol 1;TRITON X-100; TRİTON X-100; TRİTON™-X ; TRİTON X-100; 2315-67-5; OCTOXYNOL-1; OCTOXİNOL; 9002-93-1; OCTOXYNOL; OCTOXYNOL-3; TRİTON X; PRECEPTİN; TRİTON X-45; TRİTON X 45; OCTOXYNOL-9; HYDROL SW; TRİTON X 100; TRİTON X 305; ALFENOL 3; ALFENOL 9; MARLOPHEN 820; NEUTRONYX 605; OCTOXİNOLUM; POLETOXOL; CONCO NİX-100; HYONİC PE-250; TRİTON X 35; ANTAROX A-200; ORTHO-GYNOL; IGEPAL CA-630; TRİTON X 165; TRİTON X 405; TRİTON X 705; TRİTON X-102; OCTOXYNOL-11; OCTOXYNOL-12; OCTOXYNOL-25; OCTOXYNOL-33; OCTOXYNOL-40; PEG 4-İSOOCTYLPHENYL ETHER; PEG-9 OCTYL PHENYL ETHER; 4-TERT-OCTYLPHENYL PEG ETHER; PEG 4-TERT-OCTYLPHENYL ETHER; TEXOFOR FP 300; TRİTON X 101; TRİTON X 102; ETHANOL, 2-[4-(1,1,3,3 TETRAMETHYLBUTYL) PHENOXY]-; OPE 30; 4-TERT-OCTYLPHENOL; MONOETHOXYLATE; POLYOXYETHYLENE OCTYL PHENYL ETHER; OCTOXİNOLUM [INN-LATİN]; OCTOXYNOL 1; POLY(OXYETHYLENE)-P-TERT-OCTYLPHENYL ETHER; TRITON X-100; TRİTON X-100; TRITON X 100; TRİTON X 100;  TRITON X-100; TRİTON X-100; triton™-x ; triton x-100; 2315-67-5; octoxynol-1; octoxinol; 9002-93-1; octoxynol; octoxynol-3; triton x; preceptin; triton x-45; triton x 45; octoxynol-9; hydrol sw; triton x 100; triton x 305; alfenol 3; alfenol 9; marlophen 820; neutronyx 605; octoxinolum; poletoxol; conco nix-100; hyonic pe-250; triton x 35; antarox a-200; ortho-gynol; ıgepal ca-630; triton x 165; triton x 405; triton x 705; triton x-102; octoxynol-11; octoxynol-12; octoxynol-25; octoxynol-33; octoxynol-40; peg 4-isooctylphenyl ether; peg-9 octyl phenyl ether; 4-tert-octylphenyl peg ether; peg 4-tert-octylphenyl ether; texofor fp 300; triton x 101; triton x 102; ethanol, 2-[4-(1,1,3,3 tetramethylbutyl) phenoxy]-; ope 30; 4-tert-octylphenol; monoethoxylate; polyoxyethylene octyl phenyl ether; octoxinolum [ınn-latin]; octoxynol 1; poly(oxyethylene)-p-tert-octylphenyl ether; trıton x-100; triton x-100; trıton x 100; triton x 100; TRITON X-100; TRİTON X-100; Triton™-X ; Triton X-100; 2315-67-5; Octoxynol-1; Octoxinol; 9002-93-1; Octoxynol; Octoxynol-3; Triton X; Preceptin; Triton X-45; Triton X 45; Octoxynol-9; Hydrol SW; Triton X 100; Triton X 305; Alfenol 3; Alfenol 9; Marlophen 820; Neutronyx 605; Octoxinolum; Poletoxol; Conco Nix-100; Hyonic Pe-250; Triton X 35; Antarox A-200; Ortho-Gynol; Igepal CA-630; Triton X 165; Triton X 405; Triton X 705; Triton X-102; Octoxynol-11; Octoxynol-12; Octoxynol-25; Octoxynol-33; Octoxynol-40; Peg 4-İsooctylphenyl Ether; PEG-9 Octyl Phenyl Ether; 4-Tert-Octylphenyl Peg Ether; Peg 4-Tert-Octylphenyl Ether; Texofor FP 300; Triton X 101; Triton X 102; Ethanol, 2-[4-(1,1,3,3 Tetramethylbutyl) Phenoxy]-; OPE 30; 4-Tert-Octylphenol; Monoethoxylate; Polyoxyethylene Octyl Phenyl Ether; Octoxinolum [INN-Latin]; Octoxynol 1; Poly(Oxyethylene)-P-Tert-Octylphenyl Ether; TRITON X-100; TRİTON X-100; TRITON X 100; TRİTON X 100;  Poly(oxyethylene)-p-tert-octylphenyl ether; TRITON X-100; TRİTON X-100; TRITON X 100; TRİTON X 100


TRİTON X-100
Triton X-100

Triton X-100
Triton X-100.png
Names
IUPAC name
2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethanol
Other names
Polyethylene glycol p-(1,1,3,3-tetramethylbutyl)-phenyl ether
Octyl phenol ethoxylate
Polyoxyethylene octyl phenyl ether
4-Octylphenol polyethoxylate
Mono 30
TX-100
t-Octylphenoxypolyethoxyethanol
Octoxynol-9
Identifiers of Triton X-100
CAS Number of Triton X-100    
9002-93-1 ☑
3D model (JSmol)    
Interactive image
ECHA InfoCard    100.123.919
PubChem CID of Triton X-100
5590
CompTox Dashboard (EPA)    
DTXSID8034085 Edit this at Wikidata
InChI[show] of Triton X-100
SMILES[show] of Triton X-100
Properties of Triton X-100
Chemical formula of Triton X-100    C
14H
22O(C
2H
4O)n (n = 9-10)
Molar mass of Triton X-100    647 g mol−1
Appearance of Triton X-100    viscous colourless liquid
Density of Triton X-100    1.07 g/cm3
Melting point of Triton X-100    6 °C (43 °F; 279 K)
Boiling point of Triton X-100    270 °C (518 °F; 543 K)
Solubility of Triton X-100 in water    Soluble
Surface tension of Triton X-100:
CMC of Triton X-100    0.22 mM [1]
Vapor pressure of Triton X-100    < 1 mmHg (130 Pa) at 20 °C
Refractive index (nD)    1.490-1.494[2]
Hazards
Safety data sheet    MSDS
Flash point of Triton X-100    251 °C (484 °F; 524 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Triton X-100 (C
14H
22O(C
2H
4O)n) is a nonionic surfactant that has a hydrophilic polyethylene oxide chain (on average it has 9.5 ethylene oxide units) and an aromatic hydrocarbon lipophilic or hydrophobic group. The hydrocarbon group is a 4-(1,1,3,3-tetramethylbutyl)-phenyl group. Triton X-100 is closely related to IGEPAL CA-630 or former Nonidet P-40, which might differ from it mainly in having slightly shorter ethylene oxide chains. Thus Triton X-100 is slightly more hydrophilic than Igepal CA-630; these two detergents may not be considered to be functionally interchangeable for most applications.[3] 
Triton X detergents are distantly related to Pluronic range of detergents marketed by BASF. The pluronics are triblock copolymers of ethylene oxide and propylene oxide with the ethylene oxide segments being more hydrophilic than the propylene oxide.


Physical properties of Triton X-100
Undiluted Triton X-100 is a clear viscous fluid (less viscous than undiluted glycerol) owing to the hydrogen bonding of its hydrophilic polyethylene oxide parts. Undiluted Triton X-100 has a viscosity 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, xylene, trichloroethylene, ethylene glycol, ethyl ether, ethyl alcohol, isopropyl alcohol, and ethylene dichloride. Triton X-100 is insoluble in kerosene, mineral spirits, and naphtha, unless a coupling agent like oleic acid is used.[5]

Uses
Triton X-100 is a commonly used detergent in laboratories.[6] Triton X-100 is widely used to lyse cells to extract protein or organelles, or to permeabilize the membranes of living cells.[7]

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 Fluzone
Permeabilizing unfixed (or lightly fixed) eukaryotic cell membranes[7]
Solubilizing membrane proteins in their native state in conjunction with zwitterionic detergents such as CHAPS
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
Apart from laboratory use, Triton X-100 can be found in several types of cleaning compounds,[8] ranging from heavy-duty industrial products to gentle detergents. It is also a popular ingredient in homemade vinyl record cleaning fluids together with distilled water and isopropyl alcohol.[9]

Triton X-100 inclusion in the Authorisation List (Annex XIV) of REACH
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[10] of the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH) Regulation which addresses the production, import and use of chemical substances and their potential impacts on human health and the environment.[11] 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.[12] The ECHA finally included the substance group in the Authorisation List (Annex XIV),[13] 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, should be soluble, easy to remove, eco-friendly, but not degrade to toxic metabolites. In a recent study,[14] 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. To date, Nereid can be produced at kilogram-scale using a three-step synthesis, and a patent has been applied for.[15] Nereid is scalable and compatible with existing processes and has not shown any impact on product activity so far. In terms of performance, Nereid would be a robust “all-in-one” replacement for Triton X-100. Thus, it is currently tested in ecotoxicology and biodegradation studies to confirm that it is environmentally safe.

Properties
Related Categories    Antigen-Vaccine Preparation, Biochemicals and Reagents, Cell Biology, Cell Culture, Cell Lysis Reagents,
Cell Signaling and Neuroscience, Core Bioreagents, Detergents, Detergents N to Z, Detergents by Applications, Diagnostic Applications, Electrophoresis Chromatography, Enzymology, Life Science Reagents for Immunohistochemistry (IHC), Membrane Protein Solubilization, Non-Ionic Detergents, Research Essentials, Signal Transduction Research Tools, Tissue Processing
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Quality Level      200
grade      laboratory grade
description      non-ionic
form      liquid
mol wt      micellar avg mol wt 80,000
     average mol wt 625
aggregation number      100-155
Show More (16) 
Description
General description
Triton X-100 has hemolytic property[6] and is used for DNA extraction.[4]

Triton X-100 is a common non-ionic surfactant and emulsifier which is often used in biochemical applications to solubilize proteins. It is considered a comparatively mild detergent, non-denaturing, and is reported in numerous references as a routinely added reagent. It is utilized for lysing cells to extract protein and cellular organelles. It can also permeabilize the living cell membrane for transfection.[1][5]

Application
Triton X-100 has been used:
• In the permeabilization of cells for immunofluorescence staining
• As a component of lysis buffer in western blot analysis
• As a component of Tris-buffered saline for the preparation of cell sections in Immunogold labelling for electron microscope
Packaging
1 L in poly bottle

100, 500 mL in poly bottle

5 gal in poly drum

1 gal in poly bottle

5 mL in glass bottle

Biochem/physiol Actions
Widely used non-ionic surfactant for recovery of membrane components under mild non-denaturing conditions.
 

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