Edetic Acid

Base Information

• Chemical Name: Edetic Acid
• CAS No.: 60-00-4
• Deprecated CAS: 13440-78-3,161122-33-4,20539-27-9,26627-46-3,30485-87-1,30485-88-2,30485-90-6,32757-10-1,94108-75-5,402925-67-1,675141-16-9,1586747-13-8,1799367-75-1,2024587-69-5,161122-33-4,20539-27-9,26627-46-3,30485-87-1,30485-88-2,30485-90-6,32757-10-1,402925-67-1,94108-75-5
• Molecular Formula: C10H16N2O8
• Molecular Weight: 292.246
• Hs Code.: 2921219000
• European Community (EC) Number: 200-529-9,200-449-4
• ICSC Number: 0886
• UN Number: 3077
• UNII: 9G34HU7RV0
• DSSTox Substance ID: DTXSID6022977
• Nikkaji Number: J4.406G
• Wikipedia: Ethylenediaminetetraacetic_acid,Sodium_calcium_edetate
• Wikidata: Q408032
• NCI Thesaurus Code: C334,C61741,C61742
• RXCUI: 1903,3755,3539
• Metabolomics Workbench ID: 43228
• ChEMBL ID: CHEMBL858
• Mol file: 60-00-4.mol

Synonyms:Acid, Edetic;Acid, Ethylenediaminetetraacetic;Acid, Ethylenedinitrilotetraacetic;Calcitetracemate, Disodium;Calcium Disodium Edetate;Calcium Disodium Versenate;Calcium Tetacine;Chelaton 3;Chromium EDTA;Copper EDTA;Coprin;Dicobalt EDTA;Dinitrilotetraacetate, Disodium Ethylene;Dinitrilotetraacetate, Ethylene;Disodium Calcitetracemate;Disodium EDTA;Disodium Ethylene Dinitrilotetraacetate;Disodium Versenate, Calcium;Distannous EDTA;Edathamil;Edetate Disodium Calcium;Edetate, Calcium Disodium;Edetates;Edetic Acid;Edetic Acid, Calcium Salt;Edetic Acid, Calcium, Sodium Salt;Edetic Acid, Chromium Salt;Edetic Acid, Dipotassium Salt;Edetic Acid, Disodium Salt;Edetic Acid, Disodium Salt, Dihydrate;Edetic Acid, Disodium, Magnesium Salt;Edetic Acid, Disodium, Monopotassium Salt;Edetic Acid, Magnesium Salt;Edetic Acid, Monopotassium Salt;Edetic Acid, Monosodium Salt;Edetic Acid, Potassium Salt;Edetic Acid, Sodium Salt;EDTA;EDTA, Chromium;EDTA, Copper;EDTA, Dicobalt;EDTA, Disodium;EDTA, Distannous;EDTA, Gallium;EDTA, Magnesium Disodium;EDTA, Potassium;EDTA, Stannous;Ethylene Dinitrilotetraacetate;Ethylene Dinitrilotetraacetate, Disodium;Ethylenediaminetetraacetic Acid;Ethylenedinitrilotetraacetic Acid;Gallium EDTA;Magnesium Disodium EDTA;N,N'-1,2-Ethanediylbis(N-(carboxymethyl)glycine);Potassium EDTA;Stannous EDTA;Tetacine, Calcium;Tetracemate;Versenate;Versenate, Calcium Disodium;Versene

Chemical Property of Edetic Acid

Chemical Property:

• Appearance/Colour: white crystals or powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 250 °C (dec.)(lit.)
• Refractive Index: n20/D 1.363
• Boiling Point: 614.2 °C at 760 mmHg
• Flash Point: 325.2 °C
• PSA: 155.68000
• Density: 1.566 g/cm³
• LogP: -2.07120
• Water Solubility.: 0.5 g/L (25℃)
• XLogP3: -5.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 292.09066547
• Heavy Atom Count: 20
• Complexity: 316

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S37/39:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Chelating Agents,Metals -> Organic Acids,Metal Salts
• Canonical SMILES: C(CN(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O
• Recent ClinicalTrials: Trial to Assess Chelation Therapy 2
• Recent EU Clinical Trials: EVALUATION OF RESPIRATORY MUSCLES` FUNCTION IN PATIENTS AFFECTED BY ALS WITH HEAVY METAL POISONING
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly.
• Effects of Short Term Exposure: The substance is irritating to the eyes.
• Medical Use and Chelating Properties: Edetic Acid (EDTA) is utilized as a medication for managing and treating heavy metal toxicity. It belongs to the chelating class of drugs and is effective in binding heavy metals, aiding in their removal from the body.
• Application in Psoriasis Treatment: EDTA has been studied for over 60 years in the context of psoriasis treatment. As a metal-chelating agent, it has shown promise in managing symptoms and understanding the condition better. It helps in reducing non-specific serum protein interactions in enzyme immunoassays and is utilized in immunoanalysis to detect specific cells, such as CD3 cells.
• Enzyme Analysis and Genetic Studies: EDTA plays a crucial role in analyzing enzymes involved in biochemical pathways related to psoriasis. It stabilizes enzymes extracted from psoriatic lesions, allowing for detailed enzymatic analysis. Additionally, EDTA blood samples have been used for genotyping studies to understand genetic correlations in psoriatic patients.
• Antioxidant Properties: Some researchers have explored the antioxidant properties of EDTA in combating psoriasis. This aspect adds to the multifaceted approach in utilizing EDTA for psoriasis management.
• Controversy in Regenerative Endodontic Procedures (REPs): The effects of EDTA on regenerative endodontic procedures are controversial. While EDTA aids in releasing growth factors from dentine, some studies show negative effects on cell behavior. However, the complementary use of EDTA may help reduce endotoxins in contaminated root canals and promote the exposure of bioactive molecules essential for pulp-dentine complex regeneration.

Technology Process of Edetic Acid

There total 20 articles about Edetic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.83%

1,2-dichloro-ethane (107-06-2,52399-93-6) + iminodiacetonitrile (628-87-5) → ethylenediaminetetraacetic acid (60-00-4,94108-75-5)

Guidance literature:

1,2-dichloro-ethane; iminodiacetonitrile; With calcium oxide; In 5,5-dimethyl-1,3-cyclohexadiene; at 105 - 115 ℃; for 9.5h; Large scale;

With sodium hydroxide; In water; at 70 - 80 ℃; for 9h; Reagent/catalyst; Solvent; Temperature; Large scale;

Reference yield: 95.81%

Diethyl iminodiacetate (6290-05-7) + 1,2-dichloro-ethane (107-06-2,52399-93-6) → ethylenediaminetetraacetic acid (60-00-4,94108-75-5)

Guidance literature:

Diethyl iminodiacetate; 1,2-dichloro-ethane; With sodium hydroxide; In toluene; at 80 - 90 ℃; for 9.5h;

With sodium hydroxide; In water; at 70 - 80 ℃; for 4.5h; Reflux;

Reference yield: 95.47%

1-Bromo-2-chloroethane (107-04-0) + iminodiacetonitrile (628-87-5) → ethylenediaminetetraacetic acid (60-00-4,94108-75-5)

Guidance literature:

1-Bromo-2-chloroethane; iminodiacetonitrile; With calcium oxide; In 5,5-dimethyl-1,3-cyclohexadiene; at 105 - 115 ℃; for 9h;

With sodium hydroxide; In water; at 70 - 80 ℃; for 8.5h;

upstream raw materials:

formaldehyd

hydrogen cyanide

ethylenediamine

sodium cyanide

Downstream raw materials:

ethylenediaminetetraacetic acid tetraethyl ester

formaldehyd

carbon dioxide

ethylenediamine-N,N,N'-triacetic acid

Refernces

Substituted benzylaminoalkylindoles with preference for the σ₂ binding site

10.1016/j.ejmech.2007.09.012

The research aimed to develop new ligands with high affinity and selectivity for the s receptors, specifically focusing on the s2 subtype. The study synthesized a series of N-benzyl-3-[1-(4-fluorophenyl)-1H-indol-3-yl]-N-methylpropan-1-amines and N-benzyl-4-[1-(4-fluorophenyl)-1H-indol-3-yl]-N-methylbutan-1-amines with various substitutions on the phenyl ring. The key chemicals used included 3(1H-indol-3-yl)propanoic acid, 4-(1H-indol-3-yl)butanoic acid, LiAlH4 for reduction, 4-bromofluorobenzene for coupling, methanesulfonyl chloride for esterification, and various substituted benzylamines for final derivatization. The results indicated that phenyl substituents positively modulated the ability of these compounds to displace [3H]-DTG from s2 sites, while reducing displacement from s1 sites. The butylene derivatives showed greater binding affinity for s2 over s1 receptors, with the 2,4-dimethyl substituted butylene derivative (2l) exhibiting the highest s2 affinity (s2Ki = 5.9 nM) and selectivity (s1Ki/s2Ki = 22). The study concluded that a butylene chain separating the indole moiety from variously substituted benzylamino groups is crucial for interaction with the s2 binding site, suggesting that these structural features could be leveraged to design new s2 selective ligands with potential therapeutic applications.

Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands

10.1016/j.tet.2008.05.075

The research presents an improved one-pot synthetic platform for the preparation of functionalized 2,6-bisbenzimidazolylpyridine (Bip) derivatives, which are important ligands in the field of metal–ligand coordination and supramolecular chemistry. The new protocol significantly reduces the cost and time of previous synthetic routes, allowing for scale-up to multi-gram quantities with good yields (63–90%). Key chemicals involved in this research include o-diaminobenzene derivatives, 2,6-pyridine dicarboxylic acid, thionyl chloride, activated iron, hydrochloric acid, and ethylenediaminetetraacetic acid (EDTA). The study also explores the use of sodium dithionite as an alternative reducing agent to replace activated iron, further simplifying the synthesis process and reducing costs. The synthesized Bip derivatives exhibit mesogenic properties and can be converted into monomers suitable for polymerization, demonstrating potential applications in liquid crystalline materials and macromolecular assemblies.