Structure via PubChem · Public domain (PubChem)
EDDHA
Sign in to saveAlso known as ethylenediamine-N,N'-bis(2-hydroxyphenylacetic acid)
EDDHA or 'ethylenediamine-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.
Chemical data
- Formula
- C18H20N2O6
- Molecular weight
- 360.4 g/mol
- IUPAC name
- 2-[2-[[carboxy-(2-hydroxyphenyl)methyl]amino]ethylamino]-2-(2-hydroxyphenyl)acetic acid
- SMILES
- C1=CC=C(C(=C1)C(C(=O)O)NCCNC(C2=CC=CC=C2O)C(=O)O)O
- InChIKey
- PZZHMLOHNYWKIK-UHFFFAOYSA-N
- XLogP
- -2.2
- Polar surface area
- 139 Ų
- H-bond donors
- 6
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
174 papers- Mechanisms of EDDHA effects on the promotion of floral induction in the long-day plant Lemna minor (L.).Journal of plant physiology · 2003
- Synthesis of o,p-EDDHA and its detection as the main impurity in o,o-EDDHA commercial iron chelates.Journal of agricultural and food chemistry · 2002
- Fe uptake from meso and D,L-racemic Fe(o,o-EDDHA) isomers by strategy I and II plants.Journal of agricultural and food chemistry · 2006
- Theoretical speciation of ethylenediamine-N-(o-hydroxyphenylacetic)-N'-(p-hydroxyphenylacetic) acid (o,p-EDDHA) in agronomic conditions.Journal of agricultural and food chemistry · 2003
- Structure and fertilizer properties of byproducts formed in the synthesis of EDDHA.Journal of agricultural and food chemistry · 2006
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 360.132136
Show 2 more facts
- canonical SMILES
- C1=CC=C(C(=C1)C(C(=O)O)NCCNC(C2=CC=CC=C2O)C(=O)O)O
- chemical formula
- C₁₈H₂₀N₂O₆
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Preparation
- Uses
- References
EDDHA or 'ethylenediamine-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. [[File:EFOREWdownC2.png|thumb|left|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.
Excerpted from Wikipedia’s “EDDHA” article, available under the CC BY-SA 4.0 licence.