E385 or Disodium EDTA (Ethylenediaminetetraacetic acid disodium salt) is a chemical compound, disodium salt of EDTA, a chelator of calcium ions and, among EDTA salts, the most important.

It appears in the form of a white, odourless, tasteless powder, easily soluble in water, ammonia, aqueous solutions of sodium hydroxide, sodium carbonate, and hardly soluble in organic solvents such as diethyl ether or alcohol.

What it is used for and where

In chemistry, it is a six-atom complexation agent that regulates the equilibrium between ligand and metal ions, often added to lysate with magnesium and calcium complex ions to stabilise nucleic acid and degrade nuclease activity. It controls the polymerisation rate. It also functions as a chelating agent, i.e. an agent that binds to another to promote elimination or harmful reactions caused by metal ions and to form a stable water-soluble complex. These studies explain the mechanism (1).  It can chelate with a large majority of different metal ions other than alkali metals such as calcium, magnesium, iron, copper and other polyvalent ions.

It also works as a descaler (2) and as an antioxidant method also called the Fenton method (3).

Widely used to prevent oxidation caused by metals.

Food

Labelled with the number E385 in the list of European food additives, Disodium EDTA is a chemical compound that is added to food as a preservative and chelating agent to prevent spoilage of the product in which it is included and to counteract other ingredients.

It is found in carbonated drinks, jellies, canned beans, mayonnaise and others.

To check for its presence in food, a convenient HPLC method was developed for the quantitative determination of EDTA in food. EDTA in food samples was easily extracted with water using ultrasound. After conversion to Fe (III) complex in the presence of Fe (III) ions, EDTA was separated on a reversed-phase C30 column and detected by ultraviolet detection (260 nm). Citrate and malate, which are present in many foods, also formed Fe (III) complexes but did not interfere with the chromatographic detection of EDTA. The method allowed the determination of EDTA in food at concentrations down to 0.01 mmol/kg. Good recoveries (95.2-101%) were obtained with the standard addition method on four samples with high repeatability (RSD, 0.8-3.4%). The method was successfully applied to the analysis of EDTA in carbonated drinks, jellies, canned beans, canned maize and food supplements (4). 

Disodium EDTA is a known enhancer of iron absorption, yet the results of this study suggest that in the presence of EDTA, iron absorption occurs mainly from the paracellular rather than the regulated cellular mode, which could potentially increase its toxicity (5).

There is a maximum ADI (Acceptable Daily Intake) or GDA (Acceptable Daily Allowance) of 2.5 grams per kg body weight for this food additive (6).

Cosmetics

It acts as a chelating agent and pH adjuster in cosmetic formulations. Chelating agents are known to be cytotoxic and weakly genotoxic, but not carcinogenic as confirmed by the final report of the Expert Panel for the Review of Cosmetic Ingredients (7).

Chelating agent. It has the function of preventing unstable reactions and improving the bioavailability of chemical components within a product, and removes calcium and magnesium cations that can cause cloudiness in clear liquids.

Viscosity control agent. It controls and adapts viscosity to the required level for optimal chemical and physical stability of the product and dosage in gels, suspensions, emulsions, solutions. 

Medical

Disodium EDTA is used in the form of intravenous administration in chelation therapy for lead and heavy metal poisoning, in the treatment of calcified tendonitis, as an anticoagulant and bactericide due to its low cost.

Other uses

• additive, bleaching and fixing agent for processing colour-sensitive materials
• water purifier and cleaner
• agricultural chemicals
• plant growth inhibitor
• chemical plating, cyanide-free electroplating

For more information:

Disodium EDTA studies

Typical commercial product characteristics Ethylenediaminetetraacetic acid disodium salt

Appearance	White powder
pH	4.0-5.0
Boiling Point	>100°C    614.2°C at 760 mmHg
Melting Point	248°C
Flash Point	325.2ºC
Density	1.01 g/mL at 25°C
Vapor Pressure	1.15E-16mmHg at 25°C
Chlorides	0.01% Max
Sulphates	0.1% Max
Iron	0.001% Max
Heavy metal	0.001% Max
Chelating value	221
NTA	0.2%
Water insoluble matter	≤0.005%
Loss on drying	8.7- 11.4%
Aminotriacetic acid	≤10 ppm
Storage	2-8°C
Chemical Risk

• Molecular Formula    C₁₀H₁₈N₂Na₂O₁₀    C₁₀H₁₄N₂O₈Na₂.₂H₂O
• Linear Formula    [-CH₂N(CH₂CO₂Na)CH₂CO₂H]₂
• Molecular Weight  336.21
• Exact Mass    336.054565
• CAS    139-33-3     6831-92-6 (Ethylenediaminetetraacetic acid disodium salt dihydrate)
• UNII    
• EC Number   205-358-3
• DSSTox Substance ID  DTXSID9027073
• IUPAC  disodium;2-[2-[carboxylatomethyl(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate
• InChl=1S/C10H16N2O8.2Na/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);;/q;2*+1/p-2
• InChl Key      ZGTMUACCHSMWAC-UHFFFAOYSA-L
• SMILES   C(CN(CC(=O)O)CC(=O)[O-])N(CC(=O)O)CC(=O)[O-].[Na+].[Na+]
• MDL number  MFCD00070672
• PubChem Substance ID    329747771
• RTECS  AH4410000
• NCI    C65508
• FEMA     4520  
• HS Code          2922499990
• Beilstein     3822669
• eCl@ss    39030907
• NACRES NA.25

Synonyms : 

Ethylenediaminetetraacetic acid, Disodium salt, Disodic EDTA, Disodic edetate, Acid Edetic

References_____________________________________________________________________

(1) Retrievability of calcium hydroxide intracanal medicament with three calcium chelators, ethylenediaminetetraacetic acid, citric acid, and chitosan from root canals: An in vitro cone beam computed tomography volumetric analysis.
Raghu R, Pradeep G, Shetty A, Gautham PM, Puneetha PG, Reddy TVS.
J Conserv Dent. 2017 Jan-Feb;20(1):25-29. doi: 10.4103/0972-0707.209068.

Comparison of efficiency of ethylenediaminetetraacetic acid, citric acid, and etidronate in the removal of calcium hydroxide intracanal medicament using scanning electron microscopic analysis: An in-vitro study.
Chockattu SJ, Deepak BS, Goud KM.
J Conserv Dent. 2017 Jan-Feb;20(1):6-11. doi: 10.4103/0972-0707.209079.

(2) An in vitro study on the efficacy of removing calcium hydroxide from curved root canal systems in root canal therapy.
Wang Y, Guo LY, Fang HZ, Zou WL, Yang YM, Gao Y, Yang H, Hu T.
Int J Oral Sci. 2017 Jun;9(2):110-116. doi: 10.1038/ijos.2017.14. Epub 2017 Jun 23.

(3) Cosmeceutical Effects of Galactomannan Fraction from Arenga pinnata Fruits In vitro.
Yanti, Madriena, Ali S.
Pharmacognosy Res. 2017 Jan-Mar;9(1):39-45. doi: 10.4103/0974-8490.199773.

Effect of Selected Plant Phenolics on Fe2+-EDTA-H₂O₂ System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant Actions.
de Graft-Johnson J, Nowak D.
Molecules. 2016 Dec 31;22(1). pii: E59. doi: 10.3390/molecules22010059.

(4) Determination of ethylenediaminetetraacetic acid in foods by reversed-phase high-performance liquid chromatography.
Kemmei T, Kodama S, Yamamoto A, Inoue Y, Hayakawa K.
Food Chem. 2013 Jun 1;138(2-3):866-9. doi: 10.1016/j.foodchem.2012.11.103. Epub 2012 Dec 5.

(5) Interactions between ethylenediaminetetraacetic acid (EDTA) and iron absorption pathways, in the Caco-2 model.
Kibangou IB, Bureau F, Allouche S, Arhan P, Bouglé D.
Food Chem Toxicol. 2008 Nov;46(11):3414-6. doi: 10.1016/j.fct.2008.08.014. Epub 2008 Aug 20.

(6) http://www.fao.org/ag/agn/jecfa-additives/specs/Monograph1/Additive-164.pdf

(7) Lanigan RS, Yamarik TA. Final report on the safety assessment of EDTA, calcium disodium EDTA, diammonium EDTA, dipotassium EDTA, disodium EDTA, TEA-EDTA, tetrasodium EDTA, tripotassium EDTA, trisodium EDTA, HEDTA, and trisodium HEDTA. Int J Toxicol. 2002;21 Suppl 2:95-142. doi: 10.1080/10915810290096522.