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			{{cs1 config|name-list-style=vanc}}
	{{chembox
			{{Chembox
	| verifiedrevid = 418799358
			| Watchedfields = changed
	| Name = Triton X-100
			| verifiedrevid = 445470343
	| ImageFile = Triton X-100.png
			| Name = Triton X-100
	| ImageFile1 =
			| ImageFile = Triton X-100.svg
	| IUPACName =
			| ImageFile1 =
	| OtherNames = polyethylene glycol p-(1,1,3,3-tetramethylbutyl)-phenyl ether, <br/> octyl phenol ethoxylate, <br/> polyoxyethylene octyl phenyl ether, <br/> 4-octylphenol polyethoxylate, <br/> Mono 30, <br/> TX-100, <br/> t-octylphenoxypolyethoxyethanol, <br/> Octoxynol-9
			| IUPACName = 2-ethanol
	| Section1 = {{Chembox Identifiers
			| OtherNames = {{bulleted list|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}}
	| SMILES =
			| SystematicName =
	| CASNo_Ref = {{cascite|correct|CAS}}
			| Section1 = {{Chembox Identifiers
			| SMILES = CC(C)(C)CC(C)(C)C1=CC=C(C=C1)OCCO
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 9002-93-1		| CASNo = 9002-93-1
			| UNII_Ref = {{fdacite|correct|FDA}}
	| PubChem =
			| UNII = 3E2NC94VPF
			| PubChem = 5590
			| InChI = JYCQQPHGFMYQCF-UHFFFAOYSA-N
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	| Formula = {{chem|C|14|H|22|O(C|2|H|4|O)}}<sub>''n''</sub> (n = 9-10)		| Formula = {{chem|C|14|H|22|O(C|2|H|4|O)}}<sub>''n''</sub> (n = 9-10)
	| MolarMass =		| MolarMass = 647 g mol<sup>−1</sup>
	| Appearance = viscous colourless liquid		| Appearance = viscous colourless liquid
	| Density = 1.07&nbsp;g/cm<sup>3</sup>		| Density = 1.07&nbsp;g/cm<sup>3</sup>
	| MeltingPt = 6&nbsp;°C		| MeltingPtC = 6
			| BoilingPtC = 270
	| BoilingPt = >&nbsp;200&nbsp;°C
			| CMC = 0.22 mM <ref name="TillerEGeorge">{{cite journal|author1=Tiller George |author2=Mueller Thomas |author3= Dockter Michael |author4= Struve William | journal = Analytical Biochemistry| title = Hydrogenation of Triton X-100 eliminates its fluorescence and ultraviolet light absorption while preserving its detergent properties| year = 1984| volume = 141| issue=1 |pages = 262–266| doi = 10.1016/0003-2697(84)90455-X
	| Solubility = Soluble
			|pmid=6496933 }}</ref>
	| VaporPressure = <&nbsp;{{convert|1|mmHg|Pa|abbr=on}} at 20&nbsp;°C
			| Solubility = Soluble
			| VaporPressure = <&nbsp;{{convert|1|mmHg|Pa|abbr=on}} at 20&nbsp;°C
			| RefractIndex = 1.490-1.494<ref>{{cite web |title=Triton® X-100 - non-ionic detergent |url=https://www.sigmaaldrich.com/catalog/substance/tritonx10012345900293111?lang=en&region=US |publisher=Sigma-Aldrich |access-date=Dec 13, 2018 |archive-url=https://web.archive.org/web/20160224064040/http://www.sigmaaldrich.com/catalog/substance/tritonx10012345900293111?lang=en&region=US |archive-date=February 24, 2016 |url-status=live |via=WebCite®}}</ref>
	}}		}}
			| Section3 =
	| Section4 = {{Chembox Thermochemistry
			| Section4 = {{Chembox Thermochemistry
	}}		}}
			| Section5 =
	| Section7 = {{Chembox Hazards
			| Section6 =
	| ExternalMSDS =
			| Section7 = {{Chembox Hazards
	| NFPA-H =
			| ExternalSDS =
	| NFPA-F =
	| NFPA-R =		| NFPA-H =
			| NFPA-F =
	| FlashPt = 251&nbsp;°C
			| NFPA-R =
			| FlashPtC = 251
	}}		}}
	}}		}}
	'''Triton X-100''' ({{chem|C|14|H|22|O(C|2|H|4|O)}}<sub>''n''</sub>) is a ] ] which has a ] ] group (on average it has 9.5 ethylene oxide units) and a ] ] or ] group. The hydrocarbon group is a 4-(1,1,3,3-tetramethylbutyl)-] group. It is related to the ] range of ]s marketed by ]. The pluronics are triblock copolymers of ] and ]. The part formed from ethylene oxide is more hydrophilic than the part from propylene oxide. Triton X-100 is very viscous at room temperature and is thus easiest to use after being gently warmed.		'''Triton X-100''' ({{chem|C|14|H|22|O(C|2|H|4|O)}}<sub>''n''</sub>) is a ] ] that has a ] ] chain (on average it has 9.5 ethylene oxide units) and an aromatic ] ] or ] group. The hydrocarbon group is a 4-(])-] group. Triton X-100 is closely related to ], 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.<ref>{{cite web|url=http://www.snowpure.com/docs/triton-x-100-sigma.pdf|title=Sigma Product Information Sheet: Triton X-100|date=2002|website=snowpure.com|publisher=Sigma-Aldrich, Inc.|access-date=Dec 13, 2018}}</ref>
	Triton X-100 was originally a registered trademark of Rohm & Haas Co. It was subsequently purchased by ]. It was acquired by the ] when Dow acquired Union Carbide. Soon afterward (in 2009), Dow acquired Rohm & Haas Co. itself.		Triton X-100 was originally a registered trademark of Rohm & Haas Co. It was subsequently purchased by ] and then acquired by ] 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 ] of about 270 ] at 25&nbsp;°C which comes down to about 80 centipoise at 50&nbsp;°C. Triton X-100 is soluble at 25&nbsp;°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.<ref>{{cite web|url=http://www.shunchia.com/doc/x100.doc|title=TRITON Nonionic Surfactant X-100|publisher=Shun Chia Industrial Company Ltd.|format=DOC|archive-url=https://web.archive.org/web/20170304221647/http://www.shunchia.com/doc/x100.doc|archive-date=March 4, 2017|url-status=dead|access-date=Dec 13, 2018}}</ref>
	==Uses==		==Uses==
			Triton X-100 is a commonly used ] in laboratories.<ref>{{cite journal|last=Johnson|first=M|date=2018|title=Detergents: Triton X-100, Tween-20, and More|journal=Materials and Methods|language=en|volume=3|pages=163–72|doi=10.13070/mm.en.3.163|issn=2329-5139}}</ref> Triton X-100 is widely used to lyse cells to extract protein or organelles, or to permeabilize the membranes of living cells.<ref name="pmid120837548"/>
	{{refimprove section|date=October 2010}}
	{{prose|section|date=October 2010}}
	Triton X-100 is a commonly used ] in laboratories.<ref>{{cite web|url=http://www.exactantigen.com/review/Triton-X-100.html | title=Triton X-100|accessdate=2009-10-22|work=exactantigen.com}}</ref> For example:
	* it can be used to permeabilize unfixed (or lightly fixed) eukaryotic cell membranes
	* it is used in conjunction with ]ic detergents such as ] to solubilize ]s in their native state.
	*Can be used in ] as part of the ] (usually in a 5% solution in alkaline lysis buffer).
	*It can be used to reduce the surface tension of aqueous solutions during ] (usually in concentration of 0.1-0.5% in TBS or PBS Buffer).
	*Emerging use in dispersion of carbon materials for soft composite materials
	* it is used in microbiology to restrict colony expansion in Aspergillus nidulans
			Some applications include:
	Apart from laboratory use, Triton X-100 can be found in several types of cleaning compound,{{citation needed|date=October 2010}} ranging from heavy-duty industrial products to gentle detergents. It is also a popular ingredient in homemade ] cleaning fluids together with distilled water and ]. Triton X-100 appears as a final ingredient in several yearly influenza vaccines worldwide.
			*] of ] (e.g. ], ], ]) in manufacturing of ]
			*Industrial purpose (plating of metal)
			*], including Fluarix, Flublok, and ]
			*Permeabilizing unfixed (or lightly fixed) eukaryotic cell membranes<ref name="pmid120837548">{{cite journal|vauthors=Koley D, Bard AJ|year=2010|title=Triton X-100 concentration effects on membrane permeability of a single HeLa cell by scanning electrochemical microscopy (SECM)|journal=]|volume=107|issue=39|pages=16783–7|doi=10.1073/pnas.1011614107|pmc=2947864|pmid=20837548|doi-access=free|bibcode=2010PNAS..10716783K }}</ref>
			*Solubilizing ]s in their native state in conjunction with ]ic detergents such as ]
			*Part of the ] (usually in a 5% solution in alkaline lysis buffer) in ]
			*Reducing surface tension of aqueous solutions during ] (usually at a concentration of 0.1-0.5% in ] or ] buffer)
			*Dispersion of carbon materials for soft composite materials
			*Restricting colony expansion in ''Aspergillus nidulans'' in microbiology
			*Decellularization of animal-derived tissues
			*Removing ] from ] gels prior to renaturing the proteins within the gel
			*Disruption of cell monolayers as a positive control for ] 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 ] 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,<ref>{{cite web|url=https://www.dow.com/surfactants/products/octyl.htm|title=DOW Surfactants: Octylphenol Ethoxylates|website=dow.com|publisher=The Dow Chemical Company|access-date=Dec 13, 2018}}</ref> ranging from heavy-duty industrial products to gentle detergents. It is also a popular ingredient in homemade ] cleaning fluids together with distilled water and ].<ref>{{cite web|url=http://www.enjoythemusic.com/diy/0309/record_cleaner_diy.htm|title=DIY Record Cleaning Machine With Bonus DIY Cleaning Fluid Formulas|last=Gales|first=F|date=2009|website=Enjoy the Music.com|access-date=Dec 13, 2018}}</ref>
	==References==
	* Product detail page from Sigma-Aldrich
	* (GSK, Glaxo Smith Kline) Formulation 2010/2011
	* (Sanofi-Pasteur) Formulation September, 2009
	<references/>
			==Regulation in the European Union==
	==See also==
	]s, ]s
			In December 2012, the ] (ECHA) included the substance group “4-(1,1,3,3-tetramethylbutyl)phenol, ethoxylated” – which includes Triton X-100 – in the Candidate List of ]<ref>{{cite web|url=https://echa.europa.eu/candidate-list-table/-/dislist/details/0b0236e1807db570|title=Candidate List of substances of very high concern for Authorisation|website=European Chemicals Agency. An agency of the European Union|access-date=December 14, 2019}}</ref> of the ] (REACH) Regulation which addresses the production, import and use of chemical substances and their potential impacts on human health and the environment.<ref>{{cite web|url=https://echa.europa.eu/regulations/reach/legislation|title=REACH Legislation|website=European Chemicals Agency. An agency of the European Union|access-date=December 14, 2019}}</ref> 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.<ref>{{cite journal |last1=White|first1=R. |last2=Jobling |first2=S. |last3=Hoare |first3=S. A. |last4=Sumpter |first4=J. P. |last5=Parker |first5=M. G. |title=Environmentally persistent alkylphenolic compounds are estrogenic |journal=Endocrinology |date=1 July 1994 |volume=135 |issue=1 |pages=175–182 |doi=10.1210/endo.135.1.8013351 |pmid=8013351 |doi-access=free }}</ref> The ECHA finally included the substance group in the ],<ref>{{cite web|url=https://echa.europa.eu/authorisation-list|title=Authorisation List|website=European Chemicals Agency. An agency of the European Union|access-date=December 14, 2019}}</ref> mandating the pharmaceutical and other industries to replace this detergent by the “sunset date” January 4, 2021, thereby affecting ] 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,<ref>{{cite journal |last1=Farcet |first1=Jean-Baptiste |last2=Kindermann |first2=Johanna |last3=Karbiener |first3= Michael |last4= Kreil|first4=Thomas R. |title=Development of a Triton X-100 replacement for effective virus inactivation in biotechnology processes |journal=Engineering Reports|volume=1 |issue=5|date=12 December 2019 |doi=10.1002/eng2.12078|doi-access=free }}</ref> 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==		==External links==
	*		*
	*		* on OpenWetWare biologists' wiki
			*
	]		]
	]		]
			]
	]
	]
	]
	]
	]
	]