Triton X-100

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Triton X-100
Triton X-100.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=JYCQQPHGFMYQCF-UHFFFAOYSA-N
  • CC(C)(C)CC(C)(C)C1=CC=C(C=C1)OCCO
Properties
C
14
H
22
O(C
2
H
4
O)
n (n = 9-10)
Molar mass 647 g mol−1
Appearanceviscous 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:
CMC
0.22 mM [1]
Vapor pressure < 1 mmHg (130 Pa) at 20 °C
1.490-1.494 [2]
Hazards
Flash point 251 °C (484 °F; 524 K)
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triton X-100 (C
14
H
22
O(C
2
H
4
O)
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]

Contents

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.

Physical properties

Undiluted Triton X-100 is a clear viscous fluid (less viscous than undiluted glycerol). 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. [4]

Uses

Triton X-100 is a commonly used detergent in laboratories. [5] Triton X-100 is widely used to lyse cells to extract protein or organelles, or to permeabilize the membranes of living cells. [6]

Some applications include:

Apart from laboratory use, Triton X-100 can be found in several types of cleaning compounds, [7] 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. [8]

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 [9] 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. [10] 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. [11] The ECHA finally included the substance group in the Authorisation List (Annex XIV), [12] 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, [13] 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.

Related Research Articles

Detergent Surfactants with cleansing properties, even in dilute solutions

A detergent is a surfactant or a mixture of surfactants with cleansing properties when in dilute solutions. There are a large variety of detergents; often they are the sodium salts of long chain alkyl hydrogen sulphate or a long chain of benzene sulphonic acid. The most commonly found detergents are alkylbenzene sulfonates: a family of soap-like compounds that are more soluble in hard water, because the polar sulfonate is less likely than the polar carboxylate to bind to calcium and other ions found in hard water.

Surfactant Substance that lowers the surface tension between a liquid and another material

Surfactants are compounds that lower the surface tension between two liquids, between a gas and a liquid, or between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming agents, or dispersants. The word "surfactant" is a blend of surface-active agent, coined c.  1950.

A lysis buffer is a buffer solution used for the purpose of breaking open cells for use in molecular biology experiments that analyze the labile macromolecules of the cells. Most lysis buffers contain buffering salts and ionic salts to regulate the pH and osmolarity of the lysate. Sometimes detergents are added to break up membrane structures. For lysis buffers targeted at protein extraction, protease inhibitors are often included, and in difficult cases may be almost required. Lysis buffers can be used on both animal and plant tissue cells.

<i>n</i>-Octyl <i>beta</i>-<small>D</small>-thioglucopyranoside Chemical compound

n-Octyl β-d-thioglucopyranoside is a mild nonionic detergent that is used for cell lysis or to solubilise membrane proteins without denaturing them. This is particularly of use in order to crystallise them or to reconstitute them into lipid bilayers. It has a critical micelle concentration of 9 mM.

Ethoxylation is a chemical reaction in which ethylene oxide adds to a substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrates.

Nonylphenol Chemical compound

Nonylphenols are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail. Nonylphenols can come in numerous structures, all of which may be considered alkylphenols. They are used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers. They are used extensively in epoxy formulation in North America but its use has been phased out in Europe. These compounds are also precursors to the commercially important non-ionic surfactants alkylphenol ethoxylates and nonylphenol ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. Nonylphenol has attracted attention due to its prevalence in the environment and its potential role as an endocrine disruptor and xenoestrogen, due to its ability to act with estrogen-like activity. The estrogenicity and biodegradation heavily depends on the branching of the nonyl sidechain. Nonylphenol has been found to act as an agonist of the GPER (GPR30).

Laundry detergent Type of detergent used for cleaning laundry

Laundry detergent is a type of detergent used for cleaning dirty laundry (clothes). Laundry detergent is manufactured in powder and liquid form.

Polyethoxylated tallow amine refers to a range of non-ionic surfactants derived from animal fats (tallow). They are used primarily as emulsifiers and wetting agents for agrochemical formulations, such as pesticides and herbicides.

Ground deicing of aircraft is commonly performed in both commercial and general aviation. The fluids used in this operation are called deicing or anti-icing fluids. The initials ADF, ADAF or AAF are commonly used.

Kolliphor EL, formerly known as Cremophor EL, is the registered trademark of BASF Corp. for its version of polyethoxylated castor oil. It is prepared by reacting 35 moles of ethylene oxide with each mole of castor oil. The resulting product is a mixture : the major component is the material in which the hydroxyl groups of the castor oil triglyceride have ethoxylated with ethylene oxide to form polyethylene glycol ethers. Minor components are the polyethyelene glycol esters of ricinoleic acid, polyethyelene glycols and polyethyelene glycol ethers of glycerol. Kolliphor EL is a synthetic, nonionic surfactant used to stabilize emulsions of nonpolar materials in water.

Surfactin Chemical compound

Surfactin is a very powerful surfactant commonly used as an antibiotic. It is a bacterial cyclic lipopeptide, largely prominent for its exceptional surfactant power. Its amphiphilic properties help this substance to survive in both hydrophilic and hydrophobic environments. It is an antibiotic produced by the Gram-positive endospore-forming bacteria Bacillus subtilis. In the course of various studies of its properties, surfactin was found to exhibit effective characteristics like antibacterial, antiviral, antifungal, anti-mycoplasma and hemolytic activities.

NP-40 Chemical compound

NP-40 is a commercially available detergent with CAS Registry Number 9016-45-9. NP-40 is an ethoxylated nonylphenol for non-ionic surfactants and can act as emulsifier and demulsifier agent.

Within chemical compound surfactants, Pentaethylene glycol monododecyl ether (C12E5) is a nonionic surfactant. It is formed by the ethoxylation chemical reaction of dodecanol to give a material with 5 repeat units of ethylene glycol.

Nonoxynols also known as nonaethylene glycol or polyethylene glycol nonyl phenyl ether are mixtures of nonionic surfactants used as detergents, emulsifiers, wetting agents or defoaming agents. The most commonly discussed compound nonoxynol-9 is a spermicide, formulated primarily as a component of vaginal foams and creams. Nonoxynol was found to metabolize into free nonylphenol when administered to lab animals. Arkopal-N60, with on average 6 ethylene glycol units is a related used surfactant.

Radioimmunoprecipitation assay buffer is a lysis buffer used to lyse cells and tissue for the radio immunoprecipitation assay (RIPA). This buffer is more denaturing than NP-40 or Triton X-100 because it contains the ionic detergents SDS and sodium deoxycholate as active constituents and is particularly useful for disruption of nuclear membranes in the preparation of nuclear extracts. The RIPA buffer gives low background but can denature kinases.

Octyl glucoside is a nonionic surfactant frequently used to solubilise integral membrane proteins for studies in biochemistry. Structurally, it is a glycoside derived from glucose and octanol. Like Genapol X-100 and Triton X-100, it is a nonphysiological amphiphile that makes lipid bilayers less "stiff".

IGEPAL CA-630 is a nonionic, non-denaturing detergent. Its official IUPAC name is octylphenoxypolyethoxyethanol. IGEPAL is a registered trademark of Rhodia.

Environmental impacts of cleaning products entail the consequences that come as a result of chemical compounds in cleaning products. These cleaning products can contain chemicals that have detrimental impacts on the environment or to people.

Supravital staining

Supravital staining is a method of staining used in microscopy to examine living cells that have been removed from an organism. It differs from intravital staining, which is done by injecting or otherwise introducing the stain into the body. Thus a supravital stain may have a greater toxicity, as only a few cells need to survive it a short while. The term "vital stain" is used by some authors to refer specifically to an intravital stain, and by others interchangeably with a supravital stain, the core concept being that the cell being examined is still alive. As the cells are alive and unfixed, outside the body, supravital stains are temporary in nature.

Wastewater comes out of the laundry process with additional energy (heat), lint, soil, dyes, finishing agents, and other chemicals from detergents. Some laundry wastewater goes directly into the environment, due to the flaws of water infrastructure. The majority goes to sewage treatment plants before flowing into the environment. Some chemicals remain in the water after treatment, which may contaminate the water system. Some have argued they can be toxic to wildlife, or can lead to eutrophication.

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. PMID   6496933.
  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. "TRITON Nonionic Surfactant X-100". Shun Chia Industrial Company Ltd. Archived from the original (DOC) on March 4, 2017. Retrieved Dec 13, 2018.
  5. 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.
  6. 1 2 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.
  7. "DOW Surfactants: Octylphenol Ethoxylates". dow.com. The Dow Chemical Company. Retrieved Dec 13, 2018.
  8. Gales, F (2009). "DIY Record Cleaning Machine With Bonus DIY Cleaning Fluid Formulas". Enjoy the Music.com. Retrieved Dec 13, 2018.
  9. "Candidate List of substances of very high concern for Authorisation". European Chemicals Agency. An agency of the European Union. Retrieved December 14, 2019.
  10. "REACH Legislation". European Chemicals Agency. An agency of the European Union. Retrieved December 14, 2019.
  11. 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.
  12. "Authorisation List". European Chemicals Agency. An agency of the European Union. Retrieved December 14, 2019.
  13. 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 .