EDTA

Title: EDTA
CAS Registry Number: 60-00-4
CAS Name: N,N¢-1,2-Ethanediylbis[N-(carboxymethyl)glycine]
Additional Names: ethylenebis(iminodiacetic acid); (ethylenedinitrilo)tetraacetic acid; ethylenediaminetetraacetic acid; edathamil; edetic acid
Trademarks: Versene Acid (Dow)
Molecular Formula: C10H16N2O8
Molecular Weight: 292.24
Percent Composition: C 41.10%, H 5.52%, N 9.59%, O 43.80%
Literature References: Powerful chelating agent; forms stable complexes with most metal ions. Prepn: F. Münz, US 2130505 (1938 to General Aniline); R. Smith et al., J. Org. Chem. 14, 355 (1949). Prepn of a- and b-form of crystals: R. B. Le Blanc, H. L. Spell, J. Phys. Chem. 64, 949 (1960). Efficacy in animal models of cadmium toxicity: L. R. Cantilena, Jr., C. D. Klaassen, Toxicol. Appl. Pharmacol. 53, 510 (1980). Lead mobilization by calcium and zinc salts: C. F. Brownie, A. L. Aronson, ibid. 75, 167 (1984). Determn in pharmaceutical formulations and foods: A. A. Krokidis et al., Anal. Chim. Acta 535, 57 (2005). Clinical evaluation in calcific band keratopathy: D. M. Najjar et al., Am. J. Ophthalmol. 137, 1056 (2004). Review of laboratory uses: W. C. Broad, Am. Lab. 3, 47-51 (1971); of toxicology: K. Heindorff et al., Mutat. Res. 115, 149-173 (1983); of use in personal care products: J. R. Hart, Cosmet. Toiletries 98, 54-58 (1983); of determn methods: M. Sillanpää, M.-L. Sihvonen, Talanta 44, 1487-1497 (1997); of properties and analysis methods: F. Belal, A. A. Al-Badr, Anal. Profiles Drug Subs. Excip. 29, 57-104 (2002); of safety and efficacy in chelation therapy in atherosclerosis: M. T. Grier, D. G. Meyers, Ann. Pharmacother. 27, 1504-1509 (1993); E. Ernst, Am. Heart J. 140, 139-141 (2000). Safety assessment: Int. J. Toxicol. 21, (Suppl. 2), 95-142 (2002).
Properties: White, crystalline powder, mp 240-241° (dec). Soly in water at 20°: 0.2 g/100 g. The free acid tends to decarboxylate when heated to temps of 150°. Stable on storage and on boiling in aq soln.
Melting point: mp 240-241° (dec)
Derivative Type: Calcium disodium salt
CAS Registry Number: 62-33-9
CAS Name: [[N,N¢-1,2-Ethanediylbis[N-(carboxymethyl)glycinato]](4-)-N,N¢,O,O¢,ON,ON¢]calciate(2-)disodium
Additional Names: edetate calcium disodium
Trademarks: Antallin; Calcium Disodium Versenate; Ledclair (Sinclair); Mosatil; Sormetal
Molecular Formula: C10H12CaN2Na2O8
Molecular Weight: 374.27
Percent Composition: C 32.09%, H 3.23%, Ca 10.71%, N 7.48%, Na 12.29%, O 34.20%
Literature References: Prepn: Astakhov, Kiseleva, Zh. Obshch. Khim. 20, 1780 (1950), C.A. 45, 2409 (1951).
Properties: Tetrahydrate, powder. Sol in water: at 30° a 0.1M soln can be prepd (pH ~7). Practically insol in organic solvents.
Derivative Type: Cobalt salt
CAS Registry Number: 36499-65-7
Additional Names: Dicobalt edetate
Trademarks: Kelocyanor (Serb)
Molecular Formula: C10H12Co2N2O8
Molecular Weight: 406.08
Percent Composition: C 29.58%, H 2.98%, Co 29.03%, N 6.90%, O 31.52%
Derivative Type: Disodium salt
CAS Registry Number: 139-33-3
Additional Names: Edetate disodium; tetracemate disodium
Trademarks: Chelaplex III; Chelatran (Serb); Endrate disodium (Abbott); Titriplex III (Merck KGaA); Versene Na2 (Dow)
Molecular Formula: C10H14N2Na2O8
Molecular Weight: 336.21
Percent Composition: C 35.72%, H 4.20%, N 8.33%, Na 13.68%, O 38.07%
Properties: Dihydrate: crystals, mp 252° (dec). pH about 5.3. Soly in water at 20°: 10.8 g/100 ml.
Melting point: mp 252° (dec)
Derivative Type: Tetrasodium salt
CAS Registry Number: 64-02-8
Additional Names: Edetate sodium; tetracemate tetrasodium; tetracemin
Trademarks: Endrate Tetrasodium (Abbott); Versene 100 (Dow); Sequestrene; Trilon B (BASF); Nullapon; Complexone; Distol 8; Calsol; Syntes 12a; Nervanaid B
Molecular Formula: C10H12N2Na4O8
Molecular Weight: 380.17
Percent Composition: C 31.59%, H 3.18%, N 7.37%, Na 24.19%, O 33.67%
Properties: Powder, mp 300° (dec). Apparent density: 6.9 lb/gallon. Sol in water: about 103 g/100 ml. pH of 1% soln 11.3. Less sol in alcohol than the potassium salt.
Melting point: mp 300°
Density: Apparent density: 6.9 lb/gallon
Derivative Type: Trisodium salt
CAS Registry Number: 150-38-9
Additional Names: Edetate trisodium
Trademarks: Limclair (Sinclair); Versene-9 (Dow)
Molecular Formula: C10H13N2Na3O8
Molecular Weight: 358.19
Percent Composition: C 33.53%, H 3.66%, N 7.82%, Na 19.25%, O 35.73%
Properties: Monohydrate: crystals from water, mp >300°. More sol in water than the corresp disodium salt or free acid. pH of 1% aq soln 9.3.
Melting point: mp >300°
Use: Preservative and color retention agent in foods, flavoring agent. As antioxidant in foods. Pharmaceutic aid (chelating agent); anticoagulant for blood collection. Chelating agent in personal care products, in pulp and paper industry, in laboratory titrimetric analysis of metals and solubilization of metal compds.
Therap-Cat: Chelating agent (metal); dicobalt edetate as antidote (cyanide).
Therap-Cat-Vet: In treatment of lead and heavy metal poisoning of farm animals.
Keywords: Chelating Agent.
EEDQ Efalizumab Efaproxiral Efavirenz Eflornithine

Ethylenediaminetetraacetic acid
Skeletal formula of ethylenediaminetetraacetic acid
EDTA di-sodium salt
Disodium EDTA
Identifiers
Abbreviations EDTA, H4EDTA
CAS number 60-00-4 YesY
PubChem 6049
ChemSpider 5826 YesY
UNII 9G34HU7RV0 YesY
EC number 200-449-4
UN number 3077
DrugBank DB00974
KEGG D00052 YesY
MeSH Edetic+Acid
ChEBI CHEBI:42191 YesY
ChEMBL CHEMBL858 YesY
RTECS number AH4025000
ATC code S01XA05,V03AB03 (salts)
Beilstein Reference 1716295
Gmelin Reference 144943
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C10H16N2O8
Molar mass 292.24 g mol−1
Appearance Colourless crystals
Density 860 mg mL−1 (at 20 °C)
log P −0.836
Acidity (pKa) 1.782
Basicity (pKb) 12.215
Thermochemistry
Std enthalpy of
formation ΔfHo298
−1.7654–−1.7580 MJ mol−1
Std enthalpy of
combustion ΔcHo298
−4.4617–−4.4545 MJ mol−1
Pharmacology
Routes of
administration
  • Intramuscular
  • Intravenous
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
GHS hazard statements H319
GHS precautionary statements P305+351+338
EU Index 607-429-00-8
EU classification Irritant Xi
R-phrases R36
S-phrases (S2), S26
NFPA 704
NFPA 704.svg
0
1
0
LD50 2.580 g kg−1 (oral, rat)
Related compounds
Related alkanoic acids
  • Daminozide
  • Octopine
Related compounds
  • Triethylenetetramine
  • Tetraacetylethylenediamine
  • PMDTA
  • Bis-tris propane
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ethylenediaminetetraacetic acid, widely abbreviated as EDTA (for other names, see Table), is an aminopolycarboxylic acid and a colourless, water-soluble solid. Its conjugate base is named ethylenediaminetetraacetate. It is widely used to dissolve limescale. Its usefulness arises because of its role as a hexadentate ("six-toothed") ligand and chelating agent, i.e. its ability to "sequester" metal ions such as Ca2+ and Fe3+. After being bound by EDTA, metal ions remain in solution but exhibit diminished reactivity. EDTA is produced as several salts, notably disodium EDTA and calcium disodium EDTA.