2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetic acid

• ChemBase ID: 849
• Molecular Formular: C10H16N2O8
• Molecular Mass: 292.24264
• Monoisotopic Mass: 292.09066548
• SMILES: OC(=O)CN(CCN(CC(=O)O)CC(=O)O)CC(=O)O
• Canonical SMILES: OC(=O)CN(CC(=O)O)CCN(CC(=O)O)CC(=O)O
• InChI: InChI=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)
• InChIKey: KCXVZYZYPLLWCC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetic acid
• IUPAC Systematic name: 2-({2-[Bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetic acid
• IUPAC Traditional name: edetic acid; edta
• Brand Name: Endrate; Cheladrate; Havidote; Titriplex; Versenate
• Synonyms: N,N’-1,2-Ethanediylbis[N-(carboxymethyl)glycine; Celon ATH; Cheelox; Endrate; Ethylene-N,N'-biscarboxymethyl-N,N'-diglycine; Sequestric Acid; Sequestrol; Titriplex; Trilon BW; Trilon BX; Ethylenediamine-N,N,N',N'-tetraacetic Acid; Ethylenediaminetetraacetic acid solution; Diaminoethane-tetraacetic acid; EDTA solution; Ethylendiamin-tetraessigsäure; Ethylenedinitrilotetraacetic acid; (Ethylenedinitrilo)tetraacetic acid; Edathamil; ETHYLENEDIAMINE TETRAACETIC ACID FREE ACID; CaEDTA; Calcium Disodium Versenate; Calcium Disodium Edetate (JAN); Calcium disodium versenate (TN); Edetate calcium disodium (USP); EDT; Edetate Calcium; EDTA; Edetic Acid; ETHYLENEDIAMINETETRAACETIC ACID, ACS; ETHYLENEDIAMINE TETRAACETIC ACID; Ethylenediaminetetraacetic acid; Edetic acid; Ethylenedinitrilo-tetraacetic acid; Versene; Ethylenediaminetetraacetic acid; EDTA; Ethylenediaminetetraacetic acid, ACS; EDTA 溶液; 乙二胺四乙酸 溶液; 乙二胺四乙酸; IDRANAL™ II; 亚乙基二次氮基四乙酸; 依地酸; 乙二胺四乙酸; 乙二胺四乙酸, ACS

Database IDs

• CAS Number: 62-33-9; 60-00-4
• EC Number: 231-791-2; 200-449-4
• MDL Number: MFCD00003541
• Beilstein Number: 1716295
• Merck Index: 143517
• PubChem SID: 160964312; 24844908; 24844907; 24894634; 24894664; 46508301; 24845553; 24894713; 24867047; 24894707; 24894705
• PubChem CID: 6049
• CHEBI ID: 42191
• ATC CODE: V03AB03
• CHEMBL: 858
• Chemspider ID: 5826
• DrugBank ID: DB00974
• Gmelin ID: 144943
• KEGG ID: D00052
• MeSH Name: Edetic+Acid
• Unique Ingredient Identifier: 9G34HU7RV0
• Wikipedia Title: Ethylenediaminetetraacetic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.486185
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -10.586659
• LogD (pH = 7.4): -14.721412
• Log P: -5.221795
• Molar Refractivity: 62.3456 cm^3
• Polarizability: 24.69443 Å^3
• Polar Surface Area: 155.68 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.25
• LOG S: -1.5
• Solubility (Water): 9.26e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble0.1 M at 20 °C, clear, colorless; 1000000 mg/L at 25 oC [MEYLAN,WM et al. (1996)]; 3 M NaOH: soluble100 mg/mL
• Apperance: Colourless crystals; crystalline; powder; Powder
• Melting Point: 250 °C (dec.)(lit.); ca 245°C dec.; ca. 220 °C with decomposition
• Flash Point: > 100 °C (closed cup and DIN 51758)
• Auto Ignition Point: > 200 °C (DIN 51794)
• Density: 860 mg mL^-1 (at 20 °C); ca. 650 kg/m3 (bulk density)
• Refractive Index: n20/D 1.363
• Partition Coefficient: -0.836
• Absorption Wavelength: λ: 260 nm Amax: ≤1.00; λ: 280 nm Amax: ≤0.05; λ: 280 nm Amax: ≤0.25
• Hydrophobicity(logP): -2.6
• pKa: 1.782
• pKb: 12.215
• Std enthalpy of combustion: -4.4617–-4.4545 MJ mol-1
• Std enthalpy of formation: -1.7654–-1.7580 MJ mol-1
• pH: 2.8-3.1 (20 °C, saturated aqueous solution); 8.0±0.2

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: AH4025000
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: 36; R:36/37/38-58; r36
• Safety Statements: 26; S:20-25-26-29-29-37/39-61; S:20-25-26-29-37/39-61; s2, s26
• EU Classification: M7
• EU Hazard Identification Number: 13
• Emergency Response Guidebook(ERG) Number: 171
• TSCA Listed: 是
• EU Index: 607-429-00-8
• GHS Pictograms: GHS exclamation mark; GHS07
• GHS Signal Word: WARNING; Warning
• NFPA704:
  

  0

  1

  0
• LD50: 2.580 g kg^-1 (oral, rat)
• GHS Hazard statements: 319; H319
• GHS Precautionary statements: 305+351+338; P280-P264-P305+P351+P338-P337+P313; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Intramuscular; Intravenous

Product Information

• Purity: ≥99.5%; ≥98% (complexometric); ≥98.0% (KT); ≥98.5%; ≥99% (titration); ≥99.0%; ≥99.0% (KT); ≥99.5%; ≥99.995%; 95+%; 99%; 99.4+%; 99.4-100.6%; 99.995% trace metals basis
• Concentration: ~0.5 M in H2O; 0.02% in DPBS (0.5 mM)
• Grade: ACS; ACS reagent; anhydrous; ELECTROPHORESIS; for complexometry; for molecular biology; purified grade; purum; REAGENT; SAJ special grade; TraceSELECT®
• Suitability: suitable for cell culture
• Ignition Residue: ≤0.1% (as SO4); ≤0.2%; ≤0.5%
• Impurities: ≤0.005% heavy metals (as Pb); ≤0.005% Insol. dil. NH4OH; ≤0.1% Nitrilotriacetic acid ([HOCOCH2]3N); ≤0.1% nitrilotriacetic acid (NTA) (HPLC); ≤5 mg/kg NH4; DNases, none detected; endotoxin, tested; insoluble matter, passes filter test; phosphatases, none detected; proteases, none detected; RNases, none detected
• Cation Traces: Ag: ≤0.01 mg/kg; Al: ≤0.05 mg/kg; Al: ≤10 mg/kg; As: ≤0.05 mg/kg; As: ≤0.1 mg/kg; Au: ≤0.01 mg/kg; Ba: ≤0.02 mg/kg; Ba: ≤5 mg/kg; Be: ≤0.01 mg/kg; Bi: ≤0.01 mg/kg; Bi: ≤5 mg/kg; Ca: ≤0.001%; Ca: ≤0.2 mg/kg; Ca: ≤10 mg/kg; Cd: ≤0.01 mg/kg; Cd: ≤5 mg/kg; Co: ≤0.01 mg/kg; Co: ≤5 mg/kg; Cr: ≤0.1 mg/kg; Cr: ≤5 mg/kg; Cs: ≤0.01 mg/kg; Cu: ≤0.02 mg/kg; Cu: ≤5 mg/kg; Dy: ≤0.01 mg/kg; Er: ≤0.01 mg/kg; Eu: ≤0.01 mg/kg; Fe: ≤0.005%; Fe: ≤0.5 mg/kg; Fe: ≤5 mg/kg; Fe: ≤50 mg/kg; Ga: ≤0.01 mg/kg; Gd: ≤0.01 mg/kg; Ge: ≤0.01 mg/kg; heavy metals (as Pb): ≤0.001%; Hf: ≤0.01 mg/kg; Hg: ≤0.05 mg/kg; Ho: ≤0.01 mg/kg; In: ≤0.01 mg/kg; Ir: ≤0.01 mg/kg; K: ≤0.1 mg/kg; K: ≤50 mg/kg; La: ≤0.01 mg/kg; Li: ≤0.01 mg/kg; Li: ≤5 mg/kg; Lu: ≤0.01 mg/kg; Mg: ≤0.01 mg/kg; Mg: ≤10 mg/kg; Mg: ≤5 mg/kg; Mg: ≤5 ppm; Mn: ≤0.01 mg/kg; Mn: ≤5 mg/kg; Mo: ≤0.05 mg/kg; Mo: ≤5 mg/kg; Na: ≤30 mg/kg; Na: ≤500 mg/kg; Nb: ≤0.01 mg/kg; Nd: ≤0.01 mg/kg; Ni: ≤0.02 mg/kg; Ni: ≤5 mg/kg; Os: ≤0.01 mg/kg; Pb: ≤0.01 mg/kg; Pb: ≤10 mg/kg; Pb: ≤5 mg/kg; Pd: ≤0.01 mg/kg; Pr: ≤0.01 mg/kg; Pt: ≤0.01 mg/kg; Rb: ≤0.01 mg/kg; Re: ≤0.01 mg/kg; Rh: ≤0.01 mg/kg; Ru: ≤0.01 mg/kg; Sb: ≤0.01 mg/kg; Sc: ≤0.01 mg/kg; Se: ≤0.05 mg/kg; Sm: ≤0.01 mg/kg; Sn: ≤0.01 mg/kg; Sr: ≤0.01 mg/kg; Sr: ≤5 mg/kg; Ta: ≤0.01 mg/kg; Tb: ≤0.01 mg/kg; Te: ≤0.01 mg/kg; Th: ≤0.01 mg/kg; Ti: ≤0.02 mg/kg; Tl: ≤0.01 mg/kg; Tm: ≤0.01 mg/kg; U: ≤0.01 mg/kg; V: ≤0.01 mg/kg; W: ≤0.05 mg/kg; Y: ≤0.01 mg/kg; Yb: ≤0.01 mg/L; Zn: ≤0.05 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: bromide (Br-): ≤5000 μg/kg; chloride (Cl-): ≤200 mg/kg; chloride (Cl-): ≤50 mg/kg; chloride (Cl-): ≤5000 μg/kg; fluoride (F-): ≤5000 μg/kg; nitrate (NO3-): ≤5000 μg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤500 mg/kg; sulfate (SO42-): ≤50000 μg/kg
• Sterility: sterile-filtered
• Loss on Drying: ≤0.1% loss on drying, 105 °C, 2 h; ≤0.2% loss on drying, 105°C
• Quality Level: PREMIUM
• λ: 0.1 M in 1 M NaOH; neat
• Product Line: BioUltra
• abs.: absorption/268 nm cut-off
• Linear Formula: (HO2CCH2)2NCH2CH2N(CH2CO2H)2
• Empirical Formula (Hill Notation): C10H16N2O8

DETAILS

MP Biomedicals - 02152521

Purity: 99.4 to 100.6%
Free Acid
ACS Reagent Grade

MP Biomedicals - 04800684

(EDTA) Electrophoresis Grade Purity: >99.5% Heavy metals (as Pb): <10 ppm Iron (Fe): <50 ppm Sulfated ash: <0.1% Used as a buffer component.

MP Biomedicals - 04800683

(EDTA) Electrophoresis Grade Purity: >99.5% Heavy metals (as Pb): <10 ppm Iron (Fe): <50 ppm Sulfated ash: <0.1% Used as a buffer component.

MP Biomedicals - 02101676

Free Acid
Crystalline
Purity: 99%

MP Biomedicals - 04800682

(EDTA) Electrophoresis Grade Purity: >99.5% Heavy metals (as Pb): <10 ppm Iron (Fe): <50 ppm Sulfated ash: <0.1% Used as a buffer component.

MP Biomedicals - 02194659

Cell Culture Reagent
Free Acid
Purity: 99%

DrugBank - DB00974

• Drug Groups: approved
• Description: A chelating agent (chelating agents) that sequesters a variety of polyvalent cations. It is used in pharmaceutical manufacturing and as a food additive. [PubChem]
• Indication: For 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.
• Pharmacology: Edetate calcium is a heavy metal chelating agent. The calcium in edetate calcium can be displaced by divalent or trivalent metals to form a stable water soluble complex that can be excreted in the urine. In theory, 1 g of edetate calcium can theoretically bind 620 mg of lead, but in reality only about 5 mg per gram is actually excreted into the urine in lead poisoned patients. In addition to chelating lead, edetate calcium also chelates and eliminates zinc from the body. Edetate calcium also binds cadmium, copper, iron and manganese, but to a much lesser extent than either lead or zinc. Edetate calcium is relatively ineffective for use in treating mercury, gold or arsenic poisoning.
• Toxicity: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Almost none of the compound is metabolized.
• Absorption: Poorly absorbed from the gastrointestinal tract. Well absorbed following intramuscular injection.
• Half Life: The half life of edetate calcium disodium is 20 to 60 minutes.
• Elimination: It is excreted primarily by the kidney, with about 50% excreted in one hour and over 95% within 24 hours.2 Almost none of the compound is metabolized.
• External Links: Wikipedia; RxList

Sigma Aldrich - E8008

Application
A chelator used to remove calcium from cell washing and suspension media. Reduces cell clumping.
Physical form
Solution in Dulbecco′s phosphate buffered saline without calcium and magnesium

Sigma Aldrich - E6758

Application
钙螯合剂,用于消除因痕量重金属引起的对酶催化反应的抑制。

Sigma Aldrich - 431788

Application
Calcium chelator used to eliminate inhibition of enzyme catalyzed reactions due to traces of heavy metals.
Packaging
25, 100 g in poly bottle

Sigma Aldrich - E26282

Application
Calcium chelator used to eliminate inhibition of enzyme catalyzed reactions due to traces of heavy metals.

Sigma Aldrich - 39692

Application
Calcium chelator used to eliminate inhibition of enzyme catalyzed reactions due to traces of heavy metals.
Legal Information
TraceSELECT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 31064

Application
Calcium chelator used to eliminate inhibition of enzyme catalyzed reactions due to traces of heavy metals.
General description
Visit our Titration Center to learn more.

Sigma Aldrich - 03610

Application
Calcium chelator used to eliminate inhibition of enzyme catalyzed reactions due to traces of heavy metals.
General description
Visit our Titration Center to learn more.

Sigma Aldrich - 03690

General description
EDTA has been titrated to pH 8.0 with NaOH
Application
Ethylenediaminetetraacetic acid solution can be used to study cell biology, molecular biology, bioactive small molecules, biochemicals, solutions and reagents, inorganic salts, chelators and ethylenediaminetetraacetic acid (EDTA) and EDTA solutions. Ethylenediaminetetraacetic acid solution has been used in a study to help elucidate the role of antigen retrieval in immunostaining of ethanol-fixed smears. Ethylenediaminetetraacetic acid solution has also been used in a study to assess the uptake and release of biotin-labeled fluorescein (b-FITC) as well as immobilization of biotin-labeled glucose oxidase (b-GOx) to the polyelectrolyte microcapsules with an avidin-poly(styrene sulfonate) (PSS) membrane.

Sigma Aldrich - 03620

Application
Calcium chelator used to eliminate inhibition of enzyme catalyzed reactions due to traces of heavy metals.

Sigma Aldrich - 09-1320

Application
Calcium chelator used to eliminate inhibition of enzyme catalyzed reactions due to traces of heavy metals.

Sigma Aldrich - 03609

Application
Calcium chelator used to eliminate inhibition of enzyme catalyzed reactions due to traces of heavy metals.
Other Notes
Determination of anions and metal cations by single-column chromatography with EDTA as eluent using conductivity and UV detection 1; Buffer component in DNA digest analysis with capillary electrophoresis 2

Sigma Aldrich - E9884

Application
钙螯合剂,用于消除因痕量重金属引起的对酶催化反应的抑制。
包装
1 kg in poly bottle
100, 500 g in poly bottle

Sigma Aldrich - 27248

Application
Calcium chelator used to eliminate inhibition of enzyme catalyzed reactions due to traces of heavy metals.

Sigma Aldrich - 34540

Application
Calcium chelator used to eliminate inhibition of enzyme catalyzed reactions due to traces of heavy metals.

Sigma Aldrich - EDS

Application
钙螯合剂,用于消除因痕量重金属引起的对酶催化反应的抑制。

Sigma Aldrich - ED

Application
钙螯合剂,用于消除因痕量重金属引起的对酶催化反应的抑制。
包装
1 kg in poly bottle
100, 500 g in poly bottle
5 kg in poly drum

Toronto Research Chemicals - E917745

Ethylenediamine-N,N,N’,N’-tetraacetic Acid (EDTA) is a powerful chelating agent; EDTA forms stable complexes with most metal ions. EDTA is used in treatment of lead and heavy metal poisoning of farm animals.

REFERENCES

• Heindorff, K., et al.: Mutat. Res., 115, 149 (1983)
• Grier, M.T., et al.: Ann. Pharmacother., 27, 1504 (1983)
• Krokidis, A.A., et al.: Anal. Chim. Acta, 535, 57 (1983)
• Widely-used complexing agent for many cations.