EGTA

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title: "EGTA" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["chelating-agents", "acetic-acids", "ethers"] topic_path: "general/chelating-agents" source: "https://en.wikipedia.org/wiki/EGTA" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 443717205 | ImageFile = EGTA.svg | ImageSize = 260px | ImageAlt = Skeletal formula of EGTA | ImageFile1 = EGTA 3D ball.png | ImageSize1 = 260 | ImageAlt1 = Ball-and-stick model of the EGTA molecule | Name = EGTA | PIN = 3,12-Bis(carboxymethyl)-6,9-dioxa-3,12-diazatetradecane-1,14-dioic acid | OtherNames = Triethylene glycol diamine tetraacetic acid | SystematicName = | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 5972 | UNII_Ref = | UNII = 526U7A2651 | KEGG_Ref = | KEGG = D00569 | InChI = 1/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12) | InChIKey = CPJSUEIXXCENMM-UHFFFAOYAO | InChI1 = 1/C14H24N2O10/c17-11(18)7-15(8-12(19)20)1-3-25-5-6-26-4-2-16(9-13(21)22)10-14(23)24/h1-10H2,(H,17,18)(H,19,20)(H,21,22)(H,23,24) | InChIKey1 = DEFVIWRASFVYLL-UHFFFAOYAF | ChEMBL_Ref = | ChEMBL = 240390 | StdInChI_Ref = | StdInChI = 1S/C14H24N2O10/c17-11(18)7-15(8-12(19)20)1-3-25-5-6-26-4-2-16(9-13(21)22)10-14(23)24/h1-10H2,(H,17,18)(H,19,20)(H,21,22)(H,23,24) | StdInChIKey_Ref = | StdInChIKey = DEFVIWRASFVYLL-UHFFFAOYSA-N | CASNo = 67-42-5 | CASNo_Ref = | CASNo_Comment = (free acid) | CASNo2_Ref = | CASNo2 = 13368-13-3 | CASNo2_Comment = (tetrasodium salt) | PubChem = 6207 | ChEBI_Ref = | ChEBI = 30740 | SMILES = O=C(O)CN(CC(=O)O)CCOCCOCCN(CC(=O)O)CC(=O)O | Section2 = {{Chembox Properties | C=14 | H=24 | N=2 | O=10 | Appearance = | Density = | MeltingPtC = 241 | BoilingPt = | Solubility = | pKa = 2.0, 2.68, 8.85, 9.43 | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | Section4 = | Section5 = | Section6 =

EGTA (ethylene glycol-bis(β-aminoethyl ether)-N,N,N′,N′-tetraacetic acid), also known as egtazic acid (INN, USAN), is an aminopolycarboxylic acid, a chelating agent. It is a white solid that is related to the better known EDTA. Compared to EDTA, it has a lower affinity for magnesium, making it more selective for calcium ions. It is useful in buffer solutions that resemble the environment in living cells{{cite book | first1 = Glenna C. L. | last1 = Bett | first2 = Randall L. | last2 = Rasmusson | editor1-first = Candido | editor1-last = Cabo | editor2-first = David S. | editor2-last = Rosenbaum | title = Quantitative Cardiac Electrophysiology | url = https://archive.org/details/quantitativecard00rose | url-access = limited | chapter = 1. Computer Models of Ion Channels | page = 48 | publisher = Marcel Dekker | year = 2002 | isbn = 0-8247-0774-5}} where calcium ions are usually at least a thousandfold less concentrated than magnesium.

The pKa for binding of calcium ions by tetrabasic EGTA is 11.00, but the protonated forms do not significantly contribute to binding, so at pH 7, the apparent pKa becomes 6.91. See Qin et al. for an example of a pKa calculation.

EGTA has also been used experimentally for the treatment of animals with cerium poisoning and for the separation of thorium from the mineral monazite. EGTA is used as a compound in elution buffer in the protein purification technique known as tandem affinity purification, in which recombinant fusion proteins are bound to calmodulin beads and eluted out by adding EGTA.

EGTA is often employed in dentistry and endodontics for the removal of the smear layer.

References

References

  1. (1956). "Methods of Biochemical Analysis".
  2. Pubchem. "EGTA {{!}} C14H24N2O10 - PubChem".
  3. (March 1999). "Ca2+-induced inhibition of the cardiac Ca2+ channel depends on calmodulin". [[PNAS]].

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