EDDHA

• CAS: 1170-02-1
• Catalog Number: ACM1170021
• Category: Main Products
• Molecular Weight: 360.36
• Molecular Formula: C18H20N2O6
• Synonyms: α,α'-(1,2-ethanediyldiimino)bis[2-hydroxybenzeneacetic Acid N,N'-Ethylenebis[2-(o-hydroxyphenyl)glycine; (2,2'-Ethylenediimino)bis[(2-hydroxyphenyl)acetic acid]
• Melting Point: >215 °C
• Appearance: White to Light Brown Solid
• Application: EDDHA, short for Ethylenediamine-N,N'-bis((2-hydroxyphenyl)acetic acid, is a chelating agent commonly used in inorganic fertilizers. Specifically, Fe-EDDHA is used as an iron fertilizer due to its stability over a wide pH range and its strong affinity to iron. Compared to other iron chelates like EDTA and DTPA, EDDHA has been found to be the most effective in providing plants with available iron nutrients.

Case Study

Chemical Stability Study of Fertilizer Chelates Including Fe-EDDHA

Klem-Marciniak, Ewelina, et al. Molecules, 2021, 26(7), 1933.

Ethylenediamine-N,N'-di[(ortho-hydroxyphenyl) acetic] ((o,o) EDDHA or EHPG)) and its analogues are widely recognized as highly effective chelators for addressing iron deficiency in neutral and alkaline soils and preventing chlorosis. These substances effectively deliver essential micronutrients to plants, allowing them to overcome deficiencies even in high pH soil conditions.
In order to determine the chemical stability of Fe-EDDHA and Fe-EDDHSA, the micronutrient ions and Fe-EDDHA and Fe-EDDHSA chelate contents in aqueous media at different pH values were studied. The results showed that Fe-EDDHA and Fe-EDDHSA chelates were most stable at pH 7 in aqueous solution. Their concentrations do not change over time and Fe-EDDHSA chelates are very stable in aquatic environments.
Synthesis of Fe-EDDHA Chelate
· The Fe-EDDHA chelate was synthesized using a modified one-step Mannich reaction. A mixture containing a 15-fold excess of phenol, ethylenediamine, sodium hydroxide, and 50 wt% aqueous solution of glyoxylic acid was stirred at 70 °C for 3 hours. After cooling to room temperature, water and toluene were added for extraction to remove excess phenol.
· Iron(III) nitrate nanohydrate was then added to the aqueous layer, and chelation was carried out at pH 6.5. The mixture was stirred for 3 hours before adding 50 wt% aqueous sodium hydroxide solution to adjust the pH to 7-8. The Fe-EDDHA chelate precipitated under these conditions, which was then filtered and dried to obtain the final product.

Custom Q&A

What is the molecular formula of EDDHA?

The molecular formula of EDDHA is C18H20N2O6.

What are the synonyms for EDDHA?

The synonyms for EDDHA are Eddha, Edbpha, 2,2'-(Ethane-1,2-diylbis(azanediyl))bis(2-(2-hydroxyphenyl)acetic acid), and Ethylenediamine-N,N'-bis((2-hydroxyphenyl)acetic acid).

What is the molecular weight of EDDHA?

The molecular weight of EDDHA is 360.4 g/mol.

When was EDDHA created and modified?

EDDHA was created on March 27, 2005, and modified on October 21, 2023.

What is the IUPAC name of EDDHA?

The IUPAC name of EDDHA is 2-[2-[[carboxy-(2-hydroxyphenyl)methyl]amino]ethylamino]-2-(2-hydroxyphenyl)acetic acid.

What is the InChI of EDDHA?

The InChI of EDDHA is 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).

What is the InChIKey of EDDHA?

The InChIKey of EDDHA is PZZHMLOHNYWKIK-UHFFFAOYSA-N.

What is the Canonical SMILES of EDDHA?

The Canonical SMILES of EDDHA is C1=CC=C(C(=C1)C(C(=O)O)NCCNC(C2=CC=CC=C2O)C(=O)O)O.

What are the CAS numbers associated with EDDHA?

The CAS numbers associated with EDDHA are 1170-02-1 and 6021-71-2 (iron(+3) salt).

What is the physical description of EDDHA?

EDDHA is described as a solid.