Triton X-100

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-100 was originally a registered trademark of Rohm & 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. Other trademarks for very similar compounds include Conco NI, Dowfax 9N, Igepal CO, Makon, Neutronyx 600's, Nonipol NO, Plytergent B, Renex 600's, Solar NO, Sterox, Serfonic N, T-DET-N, Tergitol NP, Triton N, etc.[4]

Triton X-100
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
3D model (JSmol)
ECHA InfoCard 100.123.919
Properties
C
14H
22O(C
2H
4O)n (n = 9-10)
Molar mass 647 g mol−1
Appearance viscous colourless liquid
Density 1.07 g/cm3
Melting point 6 °C (43 °F; 279 K)
Boiling point 270 °C (518 °F; 543 K)
Soluble
Surface tension:
0.22 mM [1]
Vapor pressure < 1 mmHg (130 Pa) at 20 °C
1.490-1.494[2]
Hazards
Safety data sheet MSDS
Flash point 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).
Y verify (what is YN ?)
Infobox references

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

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.

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References
  1. Tiller George; Mueller Thomas; Dockter Michael; Struve William (1984). "Hydrogenation of Triton X-100 eliminates its fluorescence and ultraviolet light absorption while preserving its detergent properties". Analytical Biochemistry. 141 (1): 262–266. doi:10.1016/0003-2697(84)90455-X.
  2. "Triton® X-100 - non-ionic detergent". Sigma-Aldrich. Archived from the original on February 24, 2016. Retrieved Dec 13, 2018 – via WebCite®.
  3. "Sigma Product Information Sheet: Triton X-100™" (PDF). snowpure.com. Sigma-Aldrich, Inc. 2002. Retrieved Dec 13, 2018.
  4. "Poly(oxy-1,2-ethanediyl),a-sulfo-w-(4-nonylphenoxy)-, ammonium salt(1:1)". Guidechem.com.
  5. "TRITON Nonionic Surfactant X-100". Shun Chia Industrial Company Ltd. Archived from the original (DOC) on March 4, 2017. Retrieved Dec 13, 2018.
  6. Johnson, M (2018). "Detergents: Triton X-100, Tween-20, and More". Materials and Methods. 3: 163–72. doi:10.13070/mm.en.3.163. ISSN 2329-5139.
  7. Koley D, Bard AJ (2010). "Triton X-100 concentration effects on membrane permeability of a single HeLa cell by scanning electrochemical microscopy (SECM)". Proc. Natl. Acad. Sci. U.S.A. 107 (39): 16783–7. doi:10.1073/pnas.1011614107. PMC 2947864. PMID 20837548.
  8. "DOW Surfactants: Octylphenol Ethoxylates". dow.com. The Dow Chemical Company. Retrieved Dec 13, 2018.
  9. Gales, F (2009). "DIY Record Cleaning Machine With Bonus DIY Cleaning Fluid Formulas". Enjoy the Music.com. Retrieved Dec 13, 2018.
  10. "Candidate List of substances of very high concern for Authorisation". European Chemicals Agency. An agency of the European Union. Retrieved December 14, 2019.
  11. "REACH Legislation". European Chemicals Agency. An agency of the European Union. Retrieved December 14, 2019.
  12. White, R.; Jobling, S.; Hoare, S. A.; Sumpter, J. P.; Parker, M. G. (1 July 1994). "Environmentally persistent alkylphenolic compounds are estrogenic". Endocrinology. 135 (1): 175–182. doi:10.1210/endo.135.1.8013351. PMID 8013351.
  13. "Authorisation List". European Chemicals Agency. An agency of the European Union. Retrieved December 14, 2019.
  14. Farcet, Jean-Baptiste; Kindermann, Johanna; Karbiener, Michael; Kreil, Thomas R. (12 December 2019). "Development of a Triton X-100 replacement for effective virus inactivation in biotechnology processes". Engineering Reports. 1 (5). doi:10.1002/eng2.12078.
  15. US WO2019086463 (A1), Farcet, Jean-Baptiste; Kindermann, Johanna & Tille Björn et al., "Environmentally compatible detergents for inactivation of lipid-enveloped viruses"
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