Edetic Acid (CED0004666)

Record Information
Version1.0
Creation Date2014-10-14 21:16:22 UTC
Update Date2026-05-14 16:54:37 UTC
Accession NumberCHEM003931
Identification
Common NameEdetic Acid
ClassSmall Molecule
Description
Edetic Acid (C10H16N2O8) is an exogenous organic compound with an average molecular weight of 292.24 g/mol. It exists as a solid at room temperature. Edetic Acid belongs to the tetracarboxylic acids and derivatives, a subclass of carboxylic acids and derivatives within the organic compounds. This compound serves several industrial and biological roles. It functions as a chelator (PMC11228362, PMC13486686, PMC2925124, PMC5873579, PMC6989149, PMC11190260, PMC12618441) and an anticoagulant (PMC12507951, PMC13259845, PMC4464354, PMC10936106, PMC11417148, PMC7708225). Additionally, it is utilized as an industrial chelating agent, dye, biocide, and as an industrial flavouring and nutrient, as well as an antioxidant in both industrial and biological contexts (PMC12158065). In biological systems, it acts as a ligand (PMC13091222, PMC3818381), an enzyme inhibitor (PMC8230521), and an iron chelator (PMC8112722). Edetic Acid is found in or released from 45 recorded sources. These include household cleaning and consumer products such as bleaching agents, perfumes within detergents and soaps, and smoking requisites including cigar cigarettes and non-electric simulated smoking devices. It is also associated with food, food processing, and cookware, specifically in food preservation and the preparation of malt, vinegar, wine, sparkling wine, and fermentation processes for beer. Other sources include building and construction materials like fencing, floors, stairs, and ramps, as well as household items such as key rings. Furthermore, it is found in electrical and electronic equipment, including antennas, communication cables or conductors, auxiliary devices, contacts, and conductive bodies characterized by the conductive materials. Regarding health effects, Edetic Acid is associated with hemolysis (PMC11417148).
Contaminant Type
  • Anticoagulant
  • Chelating Agent
  • Drug
  • Food Additive
  • Metabolite
  • Synthetic Compound
Chemical Structure
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
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0f6x-2971000000-52370879752b5b63ccc2Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0f6x-2971000000-52370879752b5b63ccc2Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0002-3930000000-da498c10e1988a598601Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00dl-9253520000-45cc304de47f6d8bb25fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-0190000000-ff2f56ae902dbe88ddaeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1970000000-6acfba9be031774d58fdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w2i-4980000000-7fb5e96677fc6ff6c029Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-fdc1ce0a492732d97d45Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0290000000-6ea2ca75f62b63f02ce2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-053r-8920000000-d825f98fdc0554f6dc69Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0190000000-c31f2cd2d6c009257aefNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-7aeb329bb5d0bb75f7c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ika-4900000000-f34d98ee3d0ba2dd49e4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-5ff618f36425e9cee334Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udj-0290000000-9e41e44730ef5a58a845Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0btc-6900000000-20eadce392ac9f0f0acdNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
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. Inadvertent 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.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
3070.0Log mg/kg[1700:5500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hemolysisassociated_withNot AvailablePMC11417148
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
512ContactsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
573Key RingsHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
601Lawn MowersAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
625Racing SportsRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
639Degreasing LeatherTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
645Inorganic FibresTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureBeta-lactamase VIM-1Q9XAY4Pseudomonas aeruginosaPredicted (SEA)0.0778492
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)17.5161
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)69.6751
Click to view 3D structureSodium- and chloride-dependent creatine transporter 1P48029HumansPredicted (SEA)0.311397
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)106.887
Metallo-beta-lactamase type 2 structureClick to view 3D structureMetallo-beta-lactamase type 2C7C422Klebsiella pneumoniaePredicted (SEA)1.55698
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)74.5017
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)121.99
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)393.216
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)438.758
Egl nine homolog 1 structureClick to view 3D structureEgl nine homolog 1Q9GZT9HumansPredicted (SEA)38.3018
Lysine-specific demethylase 2A structureClick to view 3D structureLysine-specific demethylase 2AQ9Y2K7HumansPredicted (SEA)31.5289
Click to view 3D structureSodium- and chloride-dependent GABA transporter 2P31646Rattus norvegicusPredicted (SEA)2.64687
Histone lysine demethylase PHF8 structureClick to view 3D structureHistone lysine demethylase PHF8Q9UPP1HumansPredicted (SEA)3.65891
Olfactory receptor 51E2 structureClick to view 3D structureOlfactory receptor 51E2Q9H255HumansPredicted (SEA)2.64687
Click to view 3D structureSuccinate receptor 1Q99MT6Mus musculusPredicted (SEA)3.58106
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)1195.06
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)1619.65
Lysine-specific demethylase 5C structureClick to view 3D structureLysine-specific demethylase 5CP41229HumansPredicted (SEA)389.869
Click to view 3D structureSodium- and chloride-dependent betaine transporterP48065HumansPredicted (SEA)2.72472
Click to view 3D structureGlutamate transporter homologO59010Pyrococcus horikoshii (strain ATCC 700860 / DSM 12428 / JCM 9974 /NBRC 100139 / OT-3)Predicted (SEA)13.935
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)1773.79
Click to view 3D structureAsc-type amino acid transporter 1P63116RatPredicted (SEA)11.6774
Click to view 3D structureN-acetylaspartylglutamate synthase AQ8IXN7HumansPredicted (SEA)30.5947
Gamma-aminobutyric acid receptor subunit rho-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit rho-1P24046HumansPredicted (SEA)2.17978
Concentrations
Not Available
External Links
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.