EDDHA

EDDHA

Names
IUPAC name 2-[2-[[2-Hydroxy-1-(2-hydroxyphenyl)-2-oxoethyl]amino]ethylamino]-2-(2-hydroxyphenyl)acetic acid
Other names Ethylenediamine-N,N'-bis(2-hydroxyphenylacetic acid
Identifiers
CAS Number	1170-02-1 N
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL21178 Y
ChemSpider	13782 Y
ECHA InfoCard
E number
PubChem CID	14432
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C18H20N2O6/c21-13-7-3-1-5-11(13)15(17(23)24)19-9-10-20-16(18(25)26)12-6-2-4-8-14(12)22/h1-8,15-16,19-22H,9-10H2,(H,23,24)(H,25,26) Y Key: PZZHMLOHNYWKIK-UHFFFAOYSA-N Y InChI=1/C18H20N2O6/c21-13-7-3-1-5-11(13)15(17(23)24)19-9-10-20-16(18(25)26)12-6-2-4-8-14(12)22/h1-8,15-16,19-22H,9-10H2,(H,23,24)(H,25,26) Key: PZZHMLOHNYWKIK-UHFFFAOYAQ
SMILES C1=CC=C(C(=C1)C(C(=O)O)NCCNC(C2=CC=CC=C2O)C(=O)O)O O=C(O)C(NCCNC(c1ccccc1O)C(=O)O)c2ccccc2O
Properties
Chemical formula	C18H20N2O6
Molar mass	360.366 g·mol−1
Appearance	White solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

EDDHA or ethylenediamine-N,N′-bis(2-hydroxyphenylacetic acid) is a chelating agent. Like EDTA, it binds metal ions as a hexadentate ligand, using two amines, two phenolate centers, and two carboxylates as the six binding sites. The complexes are typically anionic. The ligand itself is a white, water-soluble powder. Both the free ligand and its tetraanionic chelating agent are abbreviated EDDHA. In contrast to EDDHA, most related aminopolycarboxylic acid chelating agents feature tertiary amines and few have phenolate groups.

Structure of anion [Mn(EDDHA)]⁻, which is representative of related C₂-symmetric complexes.

Preparation

It is produced by the multicomponent reaction of phenol, glyoxalic acid, and ethylenediamine. In this process, the initial Schiff base condensate alkylates the phenol. Related ligands can be prepared more efficiently using para-cresol.

Uses

It is used to mobilize metal ions analogously to the use of EDTA.

EDDHA has been used in phytoextraction of lead from contaminated soils. It degrades with release of salicylic acid.