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Chemical Structure| 67-42-5 Chemical Structure| 67-42-5
Chemical Structure| 67-42-5

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EGTA is a calcium chelating agent, it's also a useful chemical in a variety of buffers. It also inhibits the zinc-dependent endopeptidases, MMPs.

Synonyms: Egtazic Acid; NSC 615010; GEDTA

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of EGTA

CAS No. :67-42-5
Formula : C14H24N2O10
M.W : 380.35
SMILES Code : O(CCN(CC(=O)O)CC(=O)O)CCOCCN(CC(=O)O)CC(=O)O
Synonyms :
Egtazic Acid; NSC 615010; GEDTA
English Name :3,12-Bis(carboxymethyl)-6,9-dioxa-3,12-diazatetradecanedioic acid
MDL No. :MFCD00004291
InChI Key :DEFVIWRASFVYLL-UHFFFAOYSA-N
Pubchem ID :6207

Safety of EGTA

Application In Synthesis of EGTA

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 67-42-5 ]

[ 67-42-5 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 67-42-5 ]
  • [ 23910-62-5 ]
YieldReaction ConditionsOperation in experiment
100% With pyridine; acetic anhydride at 65℃; for 24h; Inert atmosphere;
98% With acetic anhydride In pyridine at 65℃; for 20h;
91% Stage #1: ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid With pyridine for 0.25h; Inert atmosphere; Stage #2: With acetic anhydride at 65℃; for 24h; Inert atmosphere; Sealed tube;
  • 2
  • [ 5250-72-6 ]
  • [ 67-42-5 ]
  • [ 415962-08-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-amino-5,6-dichloro-benzene-1,3-disulfonic acid diamide; ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetone at 20℃; for 0.25h; Stage #2: With triethylamine In acetone at 4℃; Further stages.;
  • 3
  • [ 67-42-5 ]
  • [ 829-71-0 ]
  • [ 415962-17-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid; 4-(hydroxyethyl)benzenesulfonamide With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetone at 20℃; for 0.25h; Stage #2: With triethylamine In acetone at 4℃; Further stages.;
  • 4
  • [ CAS Unavailable ]
  • [ 67-42-5 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In water 2 Preparation of Disodium [[Ethylenebis(oxyethylene-nitrilo)]tetraaceto]manganese(II) Hydrate EXAMPLE 2 Preparation of Disodium [[Ethylenebis(oxyethylene-nitrilo)]tetraaceto]manganese(II) Hydrate A 2 L 3-neck, round-bottom flask was fitted with a mechanical stirrer, thermometer and nitrogen inlet. To the reaction flask was added water (205 mL), [ethylenebis(oxyethylenenitrilo)]tetraacetic acid (190.20 g), manganese carbonate (57.47 g) and an additional amount of water (250 mL). The reaction was heated to 70°-75° C. and kept at 70°-75° C. for two hours under nitrogen. The suspension cooled to room temperature and was stirred over the weekend. The tan thick suspension was diluted with deionized water (100 mL) and to the suspension was added NaHCO3 (84.01 g). The pH was 7 and the reaction mixture was filtered and treated with washed activated carbon (10 g). The carbon was filtered off and the solution had air drawn across it at room temperature to reduce the volume of solvent. The product precipitated out and was collected in a Buchner funnel on #4 Whatman paper. The material air dried overnight (160 g). The solid (pale yellow-off white in color) was dried in a forced air oven at 60° C. for six hours. The material weighed 140 g. The material was redissolved in water, filtered through a 0.45 Millipore filter and recrystallized. The results of elemental analysis were as follows: calculated for C14 H20 N2 O10 MnNa2. 5H1 O: C, 29.64; H, 5.33; N, 4.94; Mn, 9.68; Na, 8.10. Found: C, 29.48; H, 5.45; N, 4.86; Mn, 9.74; Na, 8.10.
  • 5
  • [ 67-42-5 ]
  • [ 106-94-5 ]
  • [ 95-54-5 ]
  • [ 1299486-29-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid; 1,2-diamino-benzene at 180℃; for 4h; Stage #2: propyl bromide With potassium hydroxide In dimethyl sulfoxide at 20℃; for 1.5h; 5 Synthesis Example 5The above-described ligand represented by formula (B-11) was synthesized according to the description in the Journal of American Chemical Society, Dalton Transaction, 2579 to 2593 (1987) and in Tetrahedron Letter, 29, 3033 to 3036. A mixture of 1,2-diaminobenzene and ethylene glycol bis(2-aminoethylether)-N,N,N',N'-tetraacetic acid was reacted by heating at 180° C. for 4 hours. Then, the resultant product and 1-bromopropane were reacted for 1.5 hours in dimethyl sulfoxide solution at room temperature in the presence of potassium hydroxide, to obtain the above-described ligand represented by formula (B-11).
  • 6
  • [ 67-42-5 ]
  • [ 1234368-17-2 ]
  • [ 76-05-1 ]
  • [ 1571095-57-2 ]
YieldReaction ConditionsOperation in experiment
29% Stage #1: ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid; (5)-N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: trifluoroacetic acid 42 To a mixture of ethylene glycol-bis(2-aminoethylether)-N,N,N',N'-tetraacetic acid (40 mL, 0.105 mmol, 1 equiv) in DMF (1.5 mL) at rt were added DIEA (147 μ,, 0.84 mmol, 8 equiv) and HBTU (160 mg, 0.42 mmol, 4 equiv). The mixture was stirred at rt for 0.5 h to give an activated tetraacid mixture. To a mixture of intermediate E (104.9 mg, 0.193 mol, 1.83 equiv) in DMF (0.2 mL) at rt was added the activated tetracid mixture (626 μ.) in portions over 20 minutes. The mixture was stirred at rt for 1 h and purified by prep HPLC to give 44.2 mg (29 %) of the title compound TFA salt as a pale yellow solid. MS (ES, m/z): 831 [M+3H]3+. 1H MR (400 MHz, CD3OD) δ 7.89 (d, J= 7.8 Hz, 4H), 7.77 (s, 4H), 7.66 (t, J= 7.8 Hz, 4H), 7.59 - 7.53 (m, 8H), 6.83 (s, 4H), 4.82 - 4.73 (m, 8H), 4.49 (d, J= 15.9 Hz, 4H), 3.96 - 3.85 (m, 12H), 3.82 - 3.75 (m, 4H), 3.68 - 3.50 (m, 52H), 3.45 (dt, J= 14.2, 5.5 Hz, 16H), 3.15 (s, 12H), 3.05 (t, J= 5.3 Hz, 8H).
  • 7
  • [ 67-42-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
49% With strontium(II) carbonate In water at 70℃; for 6.5h; 4 Example 4 Production of the strontium (II) complex of ethylene-bis (oxyethylenenitrilo) tetraacetic acid (SrEGTA) A suspension of strontium carbonate (1.0 g, 6.77 mmol) and ethylenebis(oxyethylenenitrilo)tetraacetic acid (2.58 g, 6.77 mmol) in water (25 ml) was stirred at 70°C for 6.5 hours. The solution became almost clear. The solution was filtered at room temperature and the filtrate was evaporated to dryness and dried in vacuo at ambient temperature. The title compound was isolated as a white crystalline material. Yield 1.54 g (49%).
  • 8
  • [ 67-42-5 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide General Procedure N: General procedure J was followed using the corresponding amine-substituted equatorially modified cGMP analogue (diisopropylethylammonium salt, 50 mM in DMSO, 1 eq)*, the linker tetra-acid (tetradiisopropylethylammonium salt, 0.25 eq)*, N,N-diisopropylethylamine (3 eq) and PyBOP (1.3 eq) to obtain the tetrameric equatorially modified cGMP analogue.*To transform the reactants into the diisopropylethylammonium salt they were subjected to N,Ndiisopropylethylamine (3 eq per acidic function) in water (0.1-0.3 M) and evaporated to dryness using a speedvac concentrator at high vacuum; In a typical experiment N,N-diisopropylethylamine (2.2 eq) and PyBOP (1.1 eq) were added successively to a solution of the corresponding carboxylic acid-substituted equatorially modified cGMP analogue (100mM in DMSO, 1 eq) and the corresponding amine (1.1 eq)*. The reaction mixture was stirred until the starting material was completely consumed or no further reaction progress wasobserved (usually < 10 mm). Water (100 pL) was added, stirring was continued for 10 mm and the solvent was removed through high vacuum evaporation with a speedvac concentrator. The residue was dissolved in water (1 mL), if necessary the pH was adjusted to 6 with NaOH (2 M) or HCI (1 M) and the solution washed with ethyl acetate (5 x). The aqueous phase was evaporated under reduced pressure using a rotary evaporator, redissolved in water, subjected to preparative reversed phase hplcand desalted, giving the coupled equatorially modified cGMP analogue.*The less valuable reactant was added in slight excess, thus for the reaction with reversed functions the amine-substituted equatorially modified cGMP analogue (100 mM in DMSO, 1 eq) and the acid reactant (1.1 eq) were used.
  • 9
  • [ CAS Unavailable ]
  • [ 67-42-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
39.39% With sodium hydroxide In water at 140℃; for 48h; High pressure; 2.2. Synthesis of [Cd3(EGTA)(H2O)5](NO3)2}n1 Cd(NO3)2.4H2O (0.616 g, 4 mmol), EGTA (0.190 g, 1 mmol), and NaOH (0.080 g, 4 mmol) were completely dissolved in H2O (10 mL) and heated together at 140 °C in Teflon vessel for 48 h. The solution was cooled to room temperature and left undisturbed. Colorless crystals were observed after 1 week. After several attempts of crystal data collections as well as refinements, highly disordered nitrate molecules were unable to locate crystallographically. However, SQUEEZE analysis from PLATON,elemental analysis and IR study of complex confirm the presence of disordered two nitrate molecules. Yield 39.39% (0.362 g). Elemental analysis (%) for C14H22N4O21Cd3, calcd: C, 18.27; H, 2.41; N, 6.09 Found: C, 18.49; H, 2.54; N, 6.42. FT-IR (KBr pellet, cm-1): 3428(b), 2925(w), 1603(s), 1504(w), 1385(s), 1254(s), 1221(m), 1112(m), 1075.24(s), 994(m), 829(s), 548(s).
  • 10
  • [ CAS Unavailable ]
  • [ 67-42-5 ]
  • [ 7732-18-5 ]
  • [ 115896-43-0 ]
YieldReaction ConditionsOperation in experiment
63% With sodium hydroxide at 100℃; Autoclave; High pressure; 2.2 Synthesis of [Cu2(EGTA)(H2O)2]·(H2O) 10mL of an aqueous solution containing Cu(NO3)2.3H2O (0.480g, 2mmol), EGTA (0.190g, 0.5mmol), and NaOH (0.080g, 2mmol) were heated together at 100°C in a Teflon vessel overnight. Then, it was cooled to room temperature. Blue color crystals were isolated at the wall of the vessel which was suitable for X-ray diffraction study. The crystals were insoluble in most of the organic solvents except hot DMSO. Yield: 63 % (0.362g). M.P. >230C, Elemental analysis (%) for C14H28N2O14Cu2, calcd: C, 29.22; H, 4.9; N, 4.87 Found: C, 29.30; H, 5.02; N, 4.66. FT-IR (KBr pellet, cm-1): 3363(b), 3119(s), 2945(w), 1626(s), 1396(s), 1298(m), 1086(m), 1027(s), 980(m), 921(s), 738(s). UV-vis. absorptions: λmax (ε x104/ M-1 cm-1): 227(1.35), 295(0.97), 381(0.62) and 681(0.31) nm.
 

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