Edetic Acid (CHEM003931)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2014-10-14 21:16:22 UTC
Update Date2016-10-28 10:02:22 UTC
Accession NumberCHEM003931
Identification
Common NameEdetic Acid
ClassSmall Molecule
DescriptionA chelating agent (chelating agents) that sequesters a variety of polyvalent cations. It is used in pharmaceutical manufacturing and as a food additive. [PubChem]
Contaminant Sources
  • Clean Air Act Chemicals
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anticoagulant
  • Chelating Agent
  • Drug
  • Food Additive
  • Metabolite
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Ethylenedinitrilo)tetraacetic acid, ion(4-)ChEBI
2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetateChEBI
Acide edetiqueChEBI
Acide ethylenediaminetetracetiqueChEBI
Acido edeticoChEBI
Acidum edeticumChEBI
EDTAChEBI
EDTA, ion(4-)ChEBI
EthylenediaminetetraacetateChEBI
H4EDtaChEBI
N,N'-1,2-ethane diylbis-(N-(carboxymethyl)glycine)ChEBI
{[-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetIC ACIDChEBI
Ethylenediaminetetraacetic acidKegg
Versene acidKegg
(Ethylenedinitrilo)tetraacetate, ion(4-)Generator
2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetic acidGenerator
{[-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetateGenerator
EdetateGenerator
CaEDTAHMDB
Calcium disodium edetateHMDB
Calcium disodium versenateHMDB
Edetate calciumHMDB
Edetate calcium disodiumHMDB
EDTHMDB
Acid, ethylenedinitrilotetraaceticHMDB
Calcium tetacineHMDB
Copper edtaHMDB
EDTA, disodiumHMDB
EDTA, distannousHMDB
EdathamilHMDB
EdetatesHMDB
Edetic acid, dipotassium saltHMDB
Edetic acid, disodium salt, dihydrateHMDB
Edetic acid, disodium, magnesium saltHMDB
Edetic acid, magnesium saltHMDB
Ethylenedinitrilotetraacetic acidHMDB
N,N'-1,2-ethanediylbis(N-(carboxymethyl)glycine)HMDB
Potassium edtaHMDB
Chromium edtaHMDB
CoprinHMDB
Dinitrilotetraacetate, ethyleneHMDB
Disodium ethylene dinitrilotetraacetateHMDB
Distannous edtaHMDB
EDTA, chromiumHMDB
EDTA, dicobaltHMDB
EDTA, galliumHMDB
EDTA, magnesium disodiumHMDB
Edetate disodium calciumHMDB
Edetic acid, disodium saltHMDB
Edetic acid, monosodium saltHMDB
Edetic acid, potassium saltHMDB
Gallium edtaHMDB
Tetacine, calciumHMDB
VerseneHMDB
Acid, ethylenediaminetetraaceticHMDB
Calcitetracemate, disodiumHMDB
Chelaton 3HMDB
Dinitrilotetraacetate, disodium ethyleneHMDB
Disodium edtaHMDB
EDTA, copperHMDB
Edetic acid, sodium saltHMDB
Ethylene dinitrilotetraacetate, disodiumHMDB
Stannous edtaHMDB
TetracemateHMDB
VersenateHMDB
Versenate, calcium disodiumHMDB
Acid, edeticHMDB
Dicobalt edtaHMDB
Disodium calcitetracemateHMDB
Disodium versenate, calciumHMDB
EDTA, potassiumHMDB
EDTA, stannousHMDB
Edetate, calcium disodiumHMDB
Edetic acid, calcium saltHMDB
Edetic acid, calcium, sodium saltHMDB
Edetic acid, chromium saltHMDB
Edetic acid, disodium, monopotassium saltHMDB
Edetic acid, monopotassium saltHMDB
Ethylene dinitrilotetraacetateHMDB
Magnesium disodium edtaHMDB
Edetic acidChEBI
Chemical FormulaC10H16N2O8
Average Molecular Mass292.243 g/mol
Monoisotopic Mass292.091 g/mol
CAS Registry Number62-33-9
IUPAC Name2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetic acid
Traditional Nameedta
SMILESOC(=O)CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O
InChI IdentifierInChI=1S/C10H16N2O8/c13-7(14)3-11(4-8(15)16)1-2-12(5-9(17)18)6-10(19)20/h1-6H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20)
InChI KeyKCXVZYZYPLLWCC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTetracarboxylic acids and derivatives
Direct ParentTetracarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tetracarboxylic acid or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amino acid or derivatives
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid
  • Carboxylic acid
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point237 °C
Boiling PointNot Available
Solubility1000000 mg/L at 25 °C
Predicted Properties
PropertyValueSource
Water Solubility9.26 g/LALOGPS
logP-1.2ALOGPS
logP-4.9ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.35ChemAxon
pKa (Strongest Basic)7.73ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area155.68 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity62.35 m³·mol⁻¹ChemAxon
Polarizability25.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f6x-2971000000-52370879752b5b63ccc2Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f6x-2971000000-52370879752b5b63ccc2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-3930000000-da498c10e1988a598601Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00dl-9253520000-45cc304de47f6d8bb25fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-0190000000-ff2f56ae902dbe88ddaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1970000000-6acfba9be031774d58fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w2i-4980000000-7fb5e96677fc6ff6c029Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-fdc1ce0a492732d97d45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0290000000-6ea2ca75f62b63f02ce2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-8920000000-d825f98fdc0554f6dc69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-c31f2cd2d6c009257aefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-7aeb329bb5d0bb75f7c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ika-4900000000-f34d98ee3d0ba2dd49e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-5ff618f36425e9cee334Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-0290000000-9e41e44730ef5a58a845Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-6900000000-20eadce392ac9f0f0acdSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposurePoorly absorbed from the gastrointestinal tract. Well absorbed following intramuscular injection.
Mechanism of ToxicityThe pharmacologic effects of edetate calcium disodium are due to the formation of chelates with divalent and trivalent metals. A stable chelate will form with any metal that has the ability to displace calcium from the molecule, a feature shared by lead, zinc, cadmium, manganese, iron and mercury. The amounts of manganese and iron metabolized are not significant. Copper is not mobilized and mercury is unavailable for chelation because it is too tightly bound to body ligands or it is stored in inaccessible body compartments. The excretion of calcium by the body is not increased following intravenous administration of edetate calcium disodium, but the excretion of zinc is considerably increased.
MetabolismAlmost none of the compound is metabolized.
Toxicity ValuesInadvertent administration of 5 times the recommended dose, infused intravenously over a 24 hour period, to an asymptomatic 16 month old patient with a blood lead content of 56 mcg/dl did not cause any ill effects. Edetate calcium disodium can aggravate the symptoms of severe lead poisoning, therefore, most toxic effects (cerebral edema, renal tubular necrosis) appear to be associated with lead poisoning. Because of cerebral edema, a therapeutic dose may be lethal to an adult or a pediatric patient with lead encephalopathy. Higher dosage of edetate calcium disodium may produce a more severe zinc deficiency.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the reduction of blood levels and depot stores of lead in lead poisoning (acute and chronic) and lead encephalopathy, in both pediatric populations and adults.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00974
HMDB IDHMDB0015109
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDEDT
Wikipedia LinkEdetate
Chemspider ID5826
ChEBI ID42191
PubChem Compound ID6049
Kegg Compound IDC00284
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Bersworth, F.C.; U.S. Patent 2,407,645; September 17,1946; assigned to The Martin Dennis Co.

MSDSNot Available
General References
1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.