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Revision as of 14:06, 24 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456919350 of page Nitrilotriacetic_acid for the Chem/Drugbox validation project (updated: 'KEGG').		Latest revision as of 08:26, 17 July 2024 edit Martinlw (talk | contribs)163 editsm →Laboratory uses
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			{{chembox
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{Chembox
	| Verifiedfields = changed		| Verifiedfields = changed
			| Watchedfields = changed
	| verifiedrevid = 394799915
			| verifiedrevid = 462261723
	| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFile = Nitrilotriacetic-acid-2D-skeletal.png		| ImageFile = Nitrilotriacetic-acid-2D-skeletal.png
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageSize = 150px
			| ImageSize = 160
	| ImageName = Wireframe model of nitrilotriacetic acid
			| ImageName = Skeletal formula of nitrilotriacetic acid
	| PIN = 2,2',2<nowiki>''</nowiki>-Nitrilotriacetic acid
			| PIN = 2,2′,2′′-Nitrilotriacetic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | pages = 21, 679 | doi = 10.1039/9781849733069 | isbn = 978-0-85404-182-4| last1 = Favre | first1 = Henri A. | last2 = Powell | first2 = Warren H. }}</ref>
	| SystematicName = 2-acetic acid
			| OtherNames = ''N'',''N''-Bis(carboxymethyl)glycine<br />2-acetic acid<ref name="pc1">{{cite web|title=Nitrilotriacetic Acid - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8758&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=13 July 2012|location=USA|date=26 March 2005|at=Identification}}</ref><br />Triglycine<ref></ref> Trilon
	| OtherNames = Triglycine
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| InChI1 = 1/C6H9NO6/c8-4(9)1-7(2-5(10)11)3-6(12)13/h1-3H2,(H,8,9)(H,10,11)(H,12,13)
	| InChIKey1 = MGFYIUFZLHCRTH-UHFFFAOYAZ
	| CASNo = 139-13-9		| CASNo = 139-13-9
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| CASNo_Comment = (free acid)
	| CASNo1 = 15934-02-8
			| CASNo2 = 5064-31-3
	| CASNo1_Comment = (monoammoniate)
			| CASNo2_Ref = {{cascite|correct|CAS}}
	| CASNo2 = 71264-32-9
	| CASNo2_Comment = (diammoniate)		| CASNo2_Comment = (trisodium salt)
			| UNII_Ref = {{fdacite|correct|FDA}}
	| PubChem = 8758
			| UNII = KA90006V9D
	| PubChem_Ref = {{Pubchemcite}}
			| UNII1_Ref = {{fdacite|correct|FDA}}
	| PubChem1 = 61821
			| UNII1 = E3C8R2M0XD
	| PubChem1_Comment = (monoammoniate)
			| UNII1_Comment = (trisodium salt)
	| PubChem1_Ref = {{Pubchemcite}}
	| PubChem2 = 62259		| PubChem = 8758
			| ChemSpiderID = 8428
	| PubChem2_Comment = (diammoniate)
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| PubChem2_Ref = {{Pubchemcite}}
	| PubChem3 = 16219712		| EINECS = 205-355-7
			| UNNumber = 2811
	| PubChem3_Comment = (monosodium)
	| PubChem3_Ref = {{Pubchemcite}}
	| PubChem4 = 23617736
	| PubChem4_Comment = (monocalcium)
	| PubChem4_Ref = {{Pubchemcite}}
	| ChemSpiderID = 8428
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID1 = 55699
	| ChemSpiderID1_Comment = (monoammoniate)
	| ChemSpiderID1_Ref = {{Chemspidercite}}
	| ChemSpiderID2 = 56063
	| ChemSpiderID2_Comment = (diammoniate)
	| ChemSpiderID2_Ref = {{Chemspidercite}}
	| ChemSpiderID3 = 17347029
	| ChemSpiderID3_Comment = (monosodium)
	| ChemSpiderID3_Ref = {{Chemspidercite}}
	| ChemSpiderID4 = 19954700
	| ChemSpiderID4_Comment = (monocalcium)
	| ChemSpiderID4_Ref = {{Chemspidercite}}
	| EINECS = 205-355-7
	| UNNumber = 2811
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB03040		| DrugBank = DB03040
	| KEGG_Ref = {{keggcite|correct|kegg}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| KEGG = <!-- blanked - oldvalue: C14695 -->		| KEGG = C14695
			| KEGG_Ref = {{keggcite|changed|kegg}}
	| MeSHName = Nitrilotriacetic+acid
			| MeSHName = Nitrilotriacetic+Acid
	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 44557		| ChEBI = 44557
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| RTECS = AJ0175000
			| RTECS = AJ0175000
	| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| Beilstein = 1710776
			| Gmelin = 3726
			| SMILES = O=C(O)CN(CC(=O)O)CC(=O)O
	| StdInChI = 1S/C6H9NO6/c8-4(9)1-7(2-5(10)11)3-6(12)13/h1-3H2,(H,8,9)(H,10,11)(H,12,13)		| StdInChI = 1S/C6H9NO6/c8-4(9)1-7(2-5(10)11)3-6(12)13/h1-3H2,(H,8,9)(H,10,11)(H,12,13)
	| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = MGFYIUFZLHCRTH-UHFFFAOYSA-N		| StdInChIKey = MGFYIUFZLHCRTH-UHFFFAOYSA-N
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| SMILES = C(C(=O)O)N(CC(=O)O)CC(=O)O
	| InChI = 1S/C6H9NO6/c8-4(9)1-7(2-5(10)11)3-6(12)13/h1-3H2,(H,8,9)(H,10,11)(H,12,13)
	| InChIKey = MGFYIUFZLHCRTH-UHFFFAOYSA-N
	| Beilstein = 1710776
	| Gmelin = 3726}}
	|Section2= {{Chembox Properties
	| C=6|H=9|N=1|O=6
	| MolarMass=191.14 g/mol
	| Appearance=
	| Density=
	| MeltingPt=
	| BoilingPt=
	| Solubility=
	}}
	|Section3= {{Chembox Hazards
	| MainHazards=
	| FlashPt=
	| Autoignition=
	}}
	}}		}}
			|Section2={{Chembox Properties
			| C=6 | H=9 | N=1 | O=6
			| MolarMass = 191.14 <ref name=ChemBK />
			| MeltingPtC = 246 <ref name=ChemBK />
			| Solubility = Insoluble. <0.01 g/100 mL at 23°C <ref name=ChemBK />
			| Appearance = White crystals
			}}
			|Section3={{Chembox Thermochemistry
			| DeltaHf = −1.3130–−1.3108 MJ mol<sup>−1</sup>
			}}
			|Section4={{Chembox Hazards
			| GHSPictograms = {{gHS exclamation mark}} {{gHS health hazard}}
			| GHSSignalWord = '''WARNING'''
			| HPhrases = {{h-phrases|302|319|351}}
			| PPhrases = {{p-phrases|281|305+351+338}}
			| FlashPtC = 100
			| LD50 = 1.1 g kg<sup>−1</sup> <small>(oral, rat)</small>
			}}
			|Section5={{Chembox Related
			| OtherFunction_label = alkanoic acids
			| OtherFunction = {{unbulleted list|]|]|]}}
			| OtherCompounds = {{unbulleted list|]|]}}
			}}
			}}
			'''Nitrilotriacetic acid''' (NTA) is the ] with the formula N(CH<sub>2</sub>CO<sub>2</sub>H)<sub>3</sub>. It is a colourless solid. Its conjugate base '''nitrilotriacetate''' is used as a ] for Ca<sup>2+</sup>, Co<sup>2+</sup>, Cu<sup>2+</sup>, and Fe<sup>3+</sup>.<ref>, International Agency for Research on Cancer</ref>
			==Production and use==
			Nitrilotriacetic acid is commercially available as the free acid and as the sodium salt. It is produced from ], ], and ] or ]. Worldwide capacity is estimated at 100 thousand tonnes per year.<ref name = Ullmann>{{Ullmann | year=2022|doi = 10.1002/14356007.a17_377.pub3 | title = Nitrilotriacetic Acid | author = Thomas Schmidt, Charalampos Gousetis, Hans-Joachim Opgenorth}}</ref> NTA is also cogenerated as an impurity in the synthesis of ], arising from reactions of the ammonia coproduct.<ref name="Ullmann/Roger">Hart, J. Roger (2005) "Ethylenediaminetetraacetic Acid and Related Chelating Agents" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a10_095}}</ref> Older routes to NTA included alkylation of ammonia with chloroacetic acid and oxidation of ].
			==Coordination chemistry and applications==
			The conjugate base of NTA is a ] ] trianionic ligand, forming ]s with a variety of metal ions.<ref>{{cite journal|author=B. L. Barnett, V. A. Uchtman|title=Structural Investigations of Calcium-Binding Molecules. 4. Calcium Binding to Aminocarboxylates. Crystal Structures of Ca(CaEDTA)<sup>.</sup>7H<sub>2</sub>O and Na(CaNTA)|journal=Inorg. Chem.|year=1979|volume=18|issue=10 |pages=2674–2678|doi=10.1021/ic50200a007}}</ref>
			Like ], its sodium salt is used for ] to remove Ca<sup>2+</sup>. For this purpose, NTA is a replacement for ], which once was widely used in detergents, and cleansers, but can cause ] of lakes.
			In one application, sodium NTA removes Cr, Cu, and As from wood that had been treated with ].<ref>Fang-Chih, C.; Ya-Nang, W.; Pin-Jui, C.; Chun-Han, K. Factors affecting chelating extraction of Cr, Cu, and As from CCA-treated wood. J. Environ. Manag. 2013, 122.</ref>
			===Laboratory uses===
			In the laboratory, this compound is used in complexometric titrations. A variant of NTA is used for protein isolation and purification in the ] method.<ref>{{cite journal|last1=Liu|first1=Weijing|title=Layer-by-Layer Deposition with Polymers Containing Nitrilotriacetate, A Convenient Route to Fabricate Metal- and Protein-Binding Films|journal=ACS Applied Materials & Interfaces|date=2016|volume=8|issue=16|pages=10164–73|doi=10.1021/acsami.6b00896|pmid=27042860}}</ref> The modified NTA is used to immobilize ] on a solid support. This allows purification of proteins containing a tag consisting of six histidine residues at either terminus.<ref></ref>
			The His-tag binds the metal of metal ] complexes. Previously, ] was used for that purpose. Now, nitrilotriacetic acid is more commonly used.<ref>{{Cite journal|last1=Lauer|first1=Sabine A.|last2=Nolan|first2=John P.|date=2002|title=Development and characterization of Ni-NTA-bearing microspheres|journal=Cytometry|volume=48|issue=3|pages=136–145|doi=10.1002/cyto.10124|pmid=12116359|issn=1097-0320|doi-access=free}}</ref>
			For laboratory uses, Ernst Hochuli et al. (1987) coupled the NTA ligand and nickel ions to ] beads.<ref>{{Cite journal|last1=Hochuli|first1=E.|last2=Döbeli|first2=H.|last3=Schacher|first3=A.|date=January 1987|title=New metal chelate adsorbent selective for proteins and peptides containing neighbouring histidine residues|journal=Journal of Chromatography A|volume=411|pages=177–184|doi=10.1016/s0021-9673(00)93969-4|pmid=3443622|issn=0021-9673}}</ref> This is the most used tool to purify His-tagged proteins via affinity chromatography.
			<gallery mode="packed" caption="NTA complexes" widths="500px" heights="100px" perrow="2">
			Ni(NTA)(aq)23views.png|Three views of the structure of <sup>−</sup>.
			File:Calcium complex of NTA trianion.svg|Structure of the nitrilotriacetate anion <sup>−</sup>.
			</gallery>
			==Toxicity and environment==
			In contrast to EDTA, NTA is easily biodegradable and is almost completely removed during wastewater treatment.<ref name=Ullmann/> The environmental impacts of NTA are minimal. Despite widespread use in cleaning products, the concentration in the water supply is too low to have a sizeable impact on human health or environmental quality.<ref>Brouwer, N.; Terpstra, P. Ecological and Toxicological Properties of Nitrilotriacetic Acid (NTA) as a Detergent Builder. Tenside Surfactants Detergents 1995, 32, 225-228.</ref>
			==Related compounds==
			* ] (MIDA), the N-methyl derivative of IDA
			* ], the amino diacetic acid
			* ], a more biodegradable analogue of NTA
			* N-hydroxyiminodiacetic acid (HIDA), {{chem2|HON(CH2CO2H)2}} (] = 87339-38-6)<ref>{{cite journal |doi=10.1002/ejoc.200601053 |title=Stabilizing Factors for Vanadium(IV) in Amavadin |date=2007 |last1=Hubregtse |first1=Ton |last2=Hanefeld |first2=Ulf |last3=Arends |first3=Isabel W. C. E. |journal=European Journal of Organic Chemistry |volume=2007 |issue=15 |pages=2413–2422 }}</ref> See ].
			==References==
			{{reflist|refs=<ref name=ChemBK>ChemBK Chemical Database http://www.chembk.com/en/chem/Nitrilotriacetic%20acid</ref>}}
			{{Authority control}}
			]
			]
			]
			]
			]