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 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL21178 ;
ChemSpider	13782 ;
ECHA InfoCard	100.013.296
PubChem CID	14432;
CompTox Dashboard (EPA)	DTXSID30864677 ;
	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) Key: PZZHMLOHNYWKIK-UHFFFAOYSA-N ; 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). verify (what is ?) 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.^[1]

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.^[2] Related ligands can be prepared more efficiently using para-cresol.^[3]

Uses

It is used to mobilize metal ions analogously to the use of EDTA.^[4]^[5]

EDDHA has been used in phytoextraction of lead from contaminated soils.^[6] It degrades with release of salicylic acid.^[7]

References

^ Bihari, S.; Smith, P. A.; Parsons, S.; Sadler, P. J. (2002). "Stereoisomers of Mn(III) Complexes of Ethylenebis[(O-Hydroxyphenyl)Glycine]". Inorganica Chimica Acta. 331: 310–317. doi:10.1016/S0020-1693(02)00690-4.
^ Hernandez-Apaolaza, Lourdes; Garcia-Marco, Sonia; Nadal, Paloma; Lucena, Juan J.; Sierra, Miguel A.; Gomez-Gallego, Mar; Ramirez-Lopez, Pedro; Escudero, Rosa (2006). "Structure and Fertilizer Properties of Byproducts Formed in the Synthesis of EDDHA". Journal of Agricultural and Food Chemistry. 54 (12): 4355–4363. doi:10.1021/jf0605749. PMID 16756367.
^ Yunta, Felipe; Garcia-Marco, Sonia; Lucena, Juan J.; Gomez-Gallego, Mar; Alcazar, Roberto; Sierra, Miguel A. (2003). "Chelating Agents Related to Ethylenediamine Bis(2-hydroxyphenyl)acetic Acid (EDDHA): Synthesis, Characterization, and Equilibrium Studies of the Free Ligands and Their Mg²⁺, Ca²⁺, Cu²⁺, and Fe³⁺ Chelates". Inorganic Chemistry. 42 (17): 5412–5421. doi:10.1021/ic034333j. PMID 12924915.
^ Diarra MS, Petitclerc D, Lacasse P (2002). "Response of Staphylococcus aureus isolates from bovine mastitis to exogenous iron sources". J. Dairy Sci. 85 (9): 2141–8. doi:10.3168/jds.S0022-0302(02)74292-6. PMID 12362445.
^ Sritharan M, Asuthkar S (2004). "Iron-regulated proteins (IRPS) of leptospira biflexa serovar Patoc strain Patoc I". Indian Journal of Medical Microbiology. 22 (2): 92–6. doi:10.1016/S0255-0857(21)02887-5. PMID 17642703.
^ Huang, Jianwei W.; Chen, Jianjun; Berti, William R.; Cunningham, Scott D. (1997). "Phytoremediation of Lead-Contaminated Soils: Role of Synthetic Chelates in Lead Phytoextraction". Environmental Science and Technology. 31 (3): 800–805. Bibcode:1997EnST...31..800H. doi:10.1021/ES9604828.
^ Pieterse, Arnold H. (2013). "Is flowering in Lemnaceae stress-induced? A review". Aquatic Botany. 104: 1–4. doi:10.1016/j.aquabot.2012.08.002.

[1] Bihari, S.; Smith, P. A.; Parsons, S.; Sadler, P. J. (2002). "Stereoisomers of Mn(III) Complexes of Ethylenebis[(O-Hydroxyphenyl)Glycine]". Inorganica Chimica Acta. 331: 310–317. doi:10.1016/S0020-1693(02)00690-4.

[2] Hernandez-Apaolaza, Lourdes; Garcia-Marco, Sonia; Nadal, Paloma; Lucena, Juan J.; Sierra, Miguel A.; Gomez-Gallego, Mar; Ramirez-Lopez, Pedro; Escudero, Rosa (2006). "Structure and Fertilizer Properties of Byproducts Formed in the Synthesis of EDDHA". Journal of Agricultural and Food Chemistry. 54 (12): 4355–4363. doi:10.1021/jf0605749. PMID 16756367.

[3] Yunta, Felipe; Garcia-Marco, Sonia; Lucena, Juan J.; Gomez-Gallego, Mar; Alcazar, Roberto; Sierra, Miguel A. (2003). "Chelating Agents Related to Ethylenediamine Bis(2-hydroxyphenyl)acetic Acid (EDDHA): Synthesis, Characterization, and Equilibrium Studies of the Free Ligands and Their Mg²⁺, Ca²⁺, Cu²⁺, and Fe³⁺ Chelates". Inorganic Chemistry. 42 (17): 5412–5421. doi:10.1021/ic034333j. PMID 12924915.

[4] Diarra MS, Petitclerc D, Lacasse P (2002). "Response of Staphylococcus aureus isolates from bovine mastitis to exogenous iron sources". J. Dairy Sci. 85 (9): 2141–8. doi:10.3168/jds.S0022-0302(02)74292-6. PMID 12362445.

[5] Sritharan M, Asuthkar S (2004). "Iron-regulated proteins (IRPS) of leptospira biflexa serovar Patoc strain Patoc I". Indian Journal of Medical Microbiology. 22 (2): 92–6. doi:10.1016/S0255-0857(21)02887-5. PMID 17642703.

[6] Huang, Jianwei W.; Chen, Jianjun; Berti, William R.; Cunningham, Scott D. (1997). "Phytoremediation of Lead-Contaminated Soils: Role of Synthetic Chelates in Lead Phytoextraction". Environmental Science and Technology. 31 (3): 800–805. Bibcode:1997EnST...31..800H. doi:10.1021/ES9604828.

[7] Pieterse, Arnold H. (2013). "Is flowering in Lemnaceae stress-induced? A review". Aquatic Botany. 104: 1–4. doi:10.1016/j.aquabot.2012.08.002.

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