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ETHYLENEDIAMINETETRAACETIC ACID

CAS Number: 60-00-4
Molecular Weight: 292.24
Beilstein: 1716295
EC Number: 200-449-4
MDL number: MFCD00003541


APPLICATIONS

In industry, Ethylenediaminetetraacetic acid, EDTA is mainly used to sequester metal ions in aqueous solution. 
In the textile industry, Ethylenediaminetetraacetic acid prevents metal ion impurities from modifying colours of dyed products. 
In the pulp and paper industry, Ethylenediaminetetraacetic acid inhibits the ability of metal ions, especially Mn2+, from catalysing the disproportionation of hydrogen peroxide, which is used in chlorine-free bleaching. 

In a similar manner, Ethylenediaminetetraacetic acid is added to some food as a preservative or stabiliser to prevent catalytic oxidative decolouration, which is catalysed by metal ions.
In soft drinks containing ascorbic acid and sodium benzoate, Ethylenediaminetetraacetic acid mitigates formation of benzene (a carcinogen).

The reduction of water hardness in laundry applications and the dissolution of scale in boilers both rely on Ethylenediaminetetraacetic acid and related complexants to bind Ca2+, Mg2+, as well as other metal ions. 
Once bound to Ethylenediaminetetraacetic acid, these metal complexes are less likely to form precipitates or to interfere with the action of the soaps and detergents. For similar reasons, cleaning solutions often contain Ethylenediaminetetraacetic acid. 
In a similar manner Ethylenediaminetetraacetic acid is used in the cement industry for the determination of free lime and free magnesia in cement and clinkers.

The solubilisation of Fe3+ ions at or below near neutral pH can be accomplished using Ethylenediaminetetraacetic acid. 
This property is useful in agriculture including hydroponics. 
However, given the pH dependence of ligand formation, Ethylenediaminetetraacetic acid is not helpful for improving iron solubility in above neutral soils.

Otherwise, at near-neutral pH and above, iron(III) forms insoluble salts, which are less bioavailable to susceptible plant species. 
Aqueous [Fe(EDTA)]− is used for removing ("scrubbing") hydrogen sulfide from gas streams. 
This conversion is achieved by oxidising the hydrogen sulfide to elemental sulfur, which is non-volatile:

2 [Fe(EDTA)]− + H2S → 2 [Fe(EDTA)]2− + S + 2 H+

In this application, the iron(III) centre is reduced to its iron(II) derivative, which can then be reoxidised by air. In similar manner, nitrogen oxides are removed from gas streams using [Fe(EDTA)]2−. 
The oxidising properties of [Fe(EDTA)]− are also exploited in photography, where it is used to solubilise silver particles.

In shampoos, cleaners, and other personal care products, Ethylenediaminetetraacetic acid salts are used as a sequestering agent to improve their stability in air.

Ethylenediaminetetraacetic acid was used in separation of the lanthanide metals by ion-exchange chromatography. 
The method relies on the steady increase in stability constant of the lanthanide Ethylenediaminetetraacetic acid complexes with atomic number. 
Using sulfonated polystyrene beads and Cu2+ as a retaining ion, Ethylenediaminetetraacetic acid causes the lanthanides to migrate down the column of resin while separating into bands of pure lanthanides. 

The lanthanides elute in order of decreasing atomic number. 
Due to the expense of this method, relative to countercurrent solvent extraction, ion exchange is now used only to obtain the highest purities of lanthanides(typically greater than 99.99%).


USE IN MEDICINE

Sodium calcium edetate, an Ethylenediaminetetraacetic acid derivative, is used to bind metal ions in the practice of chelation therapy, such as for treating mercury and lead poisoning.
Ethylenediaminetetraacetic acid is used in a similar manner to remove excess iron from the body. 
This therapy is used to treat the complication of repeated blood transfusions, as would be applied to treat thalassaemia.

Dentists and endodontists use Ethylenediaminetetraacetic acid solutions to remove inorganic debris (smear layer) and lubricate the root canals in endodontics. 
This procedure helps prepare root canals for obturation. 
Furthermore, Ethylenediaminetetraacetic acid solutions with the addition of a surfactant loosen up calcifications inside a root canal and allow instrumentation (canal shaping) and facilitate apical advancement of a file in a tight or calcified root canal towards the apex.

Ethylenediaminetetraacetic acid serves as a preservative (usually to enhance the action of another preservative such as benzalkonium chloride or thiomersal) in ocular preparations and eyedrops.

In evaluating kidney function, the chromium(III) complex [Cr(EDTA)]− (as radioactive chromium-51 (51Cr)) is administered intravenously and its filtration into the urine is monitored. 
This method is useful for evaluating glomerular filtration rate (GFR) in nuclear medicine.

Ethylenediaminetetraacetic acid is used extensively in the analysis of blood. 
Ethylenediaminetetraacetic acid is an anticoagulant for blood samples for CBC/FBCs, where the Ethylenediaminetetraacetic acid chelates the calcium present in the blood specimen, arresting the coagulation process and preserving blood cell morphology. 
Tubes containing EDTA are marked with lavender or pink tops.
Ethylenediaminetetraacetic acid is also in tan top tubes for lead testing and can be used in royal blue top tubes for trace metal testing.

Ethylenediaminetetraacetic acid is a slime dispersant, and has been found to be highly effective in reducing bacterial growth during implantation of intraocular lenses (IOLs).


LABORATORY APPLICATIONS

In the laboratory, EDTA is widely used for scavenging metal ions: In biochemistry and molecular biology, ion depletion is commonly used to deactivate metal-dependent enzymes, either as an assay for their reactivity or to suppress damage to DNA, proteins, and polysaccharides.
Ethylenediaminetetraacetic acid also acts as a selective inhibitor against dNTP hydrolyzing enzymes (Taq polymerase, dUTPase, MutT), liver arginase and horseradish peroxidase independently of metal ion chelation. 

These findings urge the rethinking of the utilisation of Ethylenediaminetetraacetic acid as a biochemically inactive metal ion scavenger in enzymatic experiments. 
In analytical chemistry, Ethylenediaminetetraacetic acid is used in complexometric titrations and analysis of water hardness or as a masking agent to sequester metal ions that would interfere with the analyses.

Ethylenediaminetetraacetic acid finds many specialised uses in the biomedical labs, such as in veterinary ophthalmology as an anticollagenase to prevent the worsening of corneal ulcers in animals. 
In tissue culture Ethylenediaminetetraacetic acid is used as a chelating agent that binds to calcium and prevents joining of cadherins between cells, preventing clumping of cells grown in liquid suspension, or detaching adherent cells for passaging. 

In histopathology, Ethylenediaminetetraacetic acid can be used as a decalcifying agent making it possible to cut sections using a microtome once the tissue sample is demineralised. 
Ethylenediaminetetraacetic acid is also known to inhibit a range of metallopeptidases, the method of inhibition occurs via the chelation of the metal ion required for catalytic activity. 
Ethylenediaminetetraacetic acid can also be used to test for bioavailability of heavy metals in sediments. 

However, it may influence the bioavailability of metals in solution, which may pose concerns regarding its effects in the environment, especially given its widespread uses and applications.
Ethylenediaminetetraacetic acid is also used to remove crud (corroded metals) from fuel rods in nuclear reactors.

Ethylenediaminetetraacetic acid is sometimes used as an ointment for skin irritations produced by metals such as chromium, nickel, and copper.

Eye drops containing Ethylenediaminetetraacetic acid are used to treat calcium deposits in the eye.

In foods, Ethylenediaminetetraacetic acid bound to iron is used to “fortify” grain-based products such as breakfast cereals and cereal bars. 
Ethylenediaminetetraacetic acid is also used to help preserve food; and to promote the color, texture, and flavor of food.

In manufacturing, Ethylenediaminetetraacetic acid is used to improve stability of some pharmaceutical products, detergents, liquid soaps, shampoos, agricultural chemical sprays, contact lens cleaners and cosmetics. 
Ethylenediaminetetraacetic acid is also used in certain blood collection tubes used by medical laboratories.


DESCRIPTION

Ethylenediaminetetraacetic acid (EDTA) is an aminopolycarboxylic acid with the formula [CH2N(CH2CO2H)2]2. 
This white, water-soluble solid is widely used to bind to iron and calcium ions. 
Ethylenediaminetetraacetic acid binds these ions as a hexadentate ("six-toothed") chelating agent. 
EDTA is produced as several salts, notably disodium EDTA, sodium calcium edetate, and tetrasodium EDTA.

Ethylenediaminetetraacetic acid is the acid form of edetate, a chelating agent with anti-hypercalcemic and anticoagulant properties. 
Ethylenediaminetetraacetic acid binds calcium and heavy metal ions, forming soluble stable complexes which are readily excreted by the kidneys. 

This results in a decrease in serum calcium levels. 
Ethylenediaminetetraacetic acid is also used as an anticoagulant for blood specimens and is applied as a treatment of lead poisoning.

Ethylenediaminetetraacetic acid is a colorless crystalline solid. 
Ethylenediaminetetraacetic acid is slightly soluble in water. 

The primary hazard is the threat to the environment. 
Immediate steps should be taken to limit its spread to the environment. 
Ethylenediaminetetraacetic acid is used in chemical analysis, to make detergents and cleaning compounds, and for many other uses.

Ethylenediaminetetraacetic acid is essentially not metabolized by the human body, and it is rapidly excreted in the urine. 
About 50% of EDTA administered intravenously is excreted within 1 h and 90% within 7 h. 
Ethylenediamine tetraacetic acid and its metal chelates do not permeate the cellular membrane to a significant extent; thus, most of the EDTA remains in the extracellular fluid until excreted in the urine.

Ethylenediaminetetraacetic acid is eliminated from the body, 95% via the kidneys and 5% by the bile, along with the metals and free ionic calcium that was bound in transit through the circulatory system. 
The binding of divalent and trivalent cations by Ethylenediamine tetraacetic acid can cause mineral deficiencies, which seem to be responsible for all of the known pharmacological and toxicological effects. 
Sensitivity to the toxic effects of Ethylenediamine tetraacetic acid is, at least in part, related to the deficiency of zinc.

Ethylenediaminetetraacetic acid is a prescription medicine, given by injection into the vein (intravenously) or into the muscle (intramuscularly).

Intravenous Ethylenediaminetetraacetic acid is used to treat lead poisoning and brain damage caused by lead poisoning; to see how well therapy for suspected lead poisoning is working; to treat poisonings by radioactive materials such as plutonium, thorium, uranium, and strontium; for removing copper in patients with a genetic disease called Wilson's disease; and for reducing levels of calcium in people whose levels are too high.

Ethylenediaminetetraacetic acid is also used intravenously for heart and blood vessel conditions including irregular heartbeat due to exposure to chemicals called cardiac glycosides, "hardening of the arteries" (atherosclerosis), chest pain (angina), high blood pressure, high cholesterol, stroke, and blood circulation problems.

Other intravenous uses include treatment of cancer, rheumatoid arthritis, osteoarthritis, an eye condition called macular degeneration, diabetes, Alzheimer's disease, multiple sclerosis, Parkinson's disease, and skin conditions including scleroderma and psoriasis.

Ethylenediaminetetraacetic acid is used in the muscle for lead poisoning and related brain damage.
Chelation therapy is a treatment that involves repeated intravenous (IV) administration of a chemical solution of ethylenediaminetetraacetic acid, or EDTA. 

Ethylenediaminetetraacetic acid is used to treat acute and chronic lead poisoning by pulling toxins (including heavy metals such as lead, cadmium, and mercury) from the bloodstream. 
The word "chelate" comes from the Greek root chele, which means "to claw." 
Ethylenediaminetetraacetic acid has a claw-like molecular structure that binds to heavy metals and other toxins.


SYNONYMS

2,2′,2′′,2′′′-(Ethane-1,2-diyldinitrilo)tetraacetic acid
EthyleneDiamineTetraAcetic acid
N,N′-Ethane-1,2-diylbis[N-(carboxymethyl)glycine]
Diaminoethane-tetraacetic acid
Edetic acid (conjugate base edetate)
EDTA
Edetic acid
Ethylenediaminetetraacetic acid
60-00-4
Endrate
 

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