3517. EDTA

Nomenclature

CAS number: 60-00-4
N,N′-1,2-Ethanediylbis[N-(carboxymethyl)glycine]; ethylenebis(iminodiacetic acid); (ethylenedinitrilo)tetraacetic acid; ethylenediaminetetraacetic acid; edathamil; edetic acid; Versene Acid (Dow).
C10H16N2O8; mol wt 292.24.
C 41.10%, H 5.52%, N 9.59%, O 43.80%.

Description and 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 α- and β-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. Sillanp"a"a, 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).

Chemical structure

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.

Derivative

Calcium disodium salt.

Nomenclature

CAS number: 62-33-9
Sodium (OC-6-21)-[[N,N′-1,2-ethanediylbis[N-[(carboxy-κO)methyl]glycinato-κN,κO]](4-)]calciate(2-) (2:1); edetate calcium disodium; Antallin; Calcium Disodium Versenate; Ledclair (Sinclair); Mosatil; Sormetal.
C10H12CaN2Na2O8; mol wt 374.27.
C 32.09%, H 3.23%, Ca 10.71%, N 7.48%, Na 12.29%, O 34.20%.

Description and 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

Cobalt salt.

Nomenclature

CAS number: 36499-65-7
Cobalt(2+) (OC-6-21)-[[N,N′-1,2-ethanediylbis[N-[(carboxy-κO)methyl]glycinato-κN,κO]](4-)]cobaltate(2-) (1:1); Dicobalt edetate; Kelocyanor (Serb).
C10H12Co2N2O8; mol wt 406.08.
C 29.58%, H 2.98%, Co 29.03%, N 6.90%, O 31.52%.

Derivative

Disodium salt.

Nomenclature

CAS number: 139-33-3; 6381-92-6 (dihydrate)
Edetate disodium; tetracemate disodium; Chelaplex III; Chelatran (Serb); Endrate disodium (Abbott); Titriplex III (Merck KGaA); Versene Na2 (Dow).
C10H14N2Na2O8; mol wt 336.21.
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.

Derivative

Tetrasodium salt.

Nomenclature

CAS number: 64-02-8
Edetate sodium; tetracemate tetrasodium; tetracemin; Endrate Tetrasodium (Abbott); Versene 100 (Dow); Sequestrene; Trilon B (BASF); Nullapon; Complexone; Distol 8; Calsol; Syntes 12a; Nervanaid B.
C10H12N2Na4O8; mol wt 380.17.
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.

Derivative

Trisodium salt.

Nomenclature

CAS number: 150-38-9; 10378-22-0 (monohydrate)
Edetate trisodium; Limclair (Sinclair); Versene-9 (Dow).
C10H13N2Na3O8; mol wt 358.19.
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.

Derivative

Magnesium disodium salt.

Nomenclature

CAS number: 14402-88-1
Sodium (OC-6-21)-[[N,N′-1,2-ethanediylbis[N-[(carboxy-κO)methyl]glycinato-κN,κO]](4-)]magnesate(2-) (2:1).
C10H12MgN2Na2O8; mol wt 358.50.
C 33.50%, H 3.37%, Mg 6.78%, N 7.81%, Na 12.83%, O 35.70%.

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.

Therapeutic Category

Chelating agent (metal); dicobalt edetate as antidote (cyanide).

Therapeutic Category (Veterinary)

In treatment of lead and heavy metal poisoning of farm animals.

Keywords

Chelating Agent

Dicobalt Edetate: Antidote (Cyanide)