Ethylenediaminetetraacetic acid

This article is about the chemical. For the medication, see Sodium calcium edetate.
"EDTA" redirects here. For other uses, see EDTA (disambiguation).
"Versene" redirects here. Not to be confused with Versine.
Ethylenediaminetetraacetic acid
3-dimensional formula of ethylenediaminetetraacetic acid
Names
IUPAC name
N,N′-(Ethane-1,2-diyl)bis[N-(carboxymethyl)glycine][1]
Systematic IUPAC name
2,2′,2′′,2′′′-(Ethane-1,2-diyldinitrilo)tetraacetic acid[1]
Other names
  • EthyleneDiamineTetraAcetic acid
  • Diaminoethane-tetraacetic acid
  • Edetic acid (conjugate base edetate) (INN, USAN)
  • Versene
Identifiers
3D model (JSmol)
Abbreviations EDTA, H4EDTA
1716295
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.409 Edit this at Wikidata
EC Number
  • 200-449-4
144943
KEGG
MeSH Edetic+Acid
RTECS number
  • AH4025000
UNII
UN number 3077
  • 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) checkY
    Key: KCXVZYZYPLLWCC-UHFFFAOYSA-N checkY
  • OC(=O)CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O
Properties
C10H16N2O8
Molar mass 292.244 g·mol−1
Appearance Colourless crystals
Density 0.860 g cm−3 (at 20 °C)
log P −0.836
Acidity (pKa) 2.0, 2.7, 6.16, 10.26[2]
Thermochemistry
−1765.4 to −1758.0 kJ mol−1
−4461.7 to −4454.5 kJ mol−1
Pharmacology
S01XA05 (WHO) V03AB03 (WHO) (salt)
  • Intramuscular
  • Intravenous
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H319
P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
Lethal dose or concentration (LD, LC):
1000 mg/kg (oral, rat)[3]
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ethylenediaminetetraacetic acid (EDTA), also called EDTA acid, is an aminopolycarboxylic acid with the formula [CH2N(CH2CO2H)2]2. This white, slightly water-soluble solid is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-soluble complexes even at neutral pH. It is thus used to dissolve Fe- and Ca-containing scale as well as to deliver iron ions under conditions where its oxides are insoluble. EDTA is available as several salts, notably disodium EDTA, sodium calcium edetate, and tetrasodium EDTA, but these all function similarly.[4]

  1. ^ a b Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 79, 123, 586, 754. ISBN 978-0-85404-182-4.
  2. ^ Raaflaub, Jürg (1956). "Applications of Metal Buffers and Metal Indicators in Biochemistry". Methods of Biochemical Analysis. Vol. 3. pp. 301–325. doi:10.1002/9780470110195.ch10. ISBN 978-0-470-30492-1. PMID 13369167.
  3. ^ Substance Name: Sodium calcium edetate. NIH.gov
  4. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).