N-(2-Acetamido)iminodiacetic acid
[CAS# 26239-55-4]

Identification

• Classification: Organic raw materials >> Amino compound >> Oxy-containing amino compound
• Name: N-(2-Acetamido)iminodiacetic acid
• Synonyms: N-(Carbamoylmethyl)iminodiacetic acid; N-(2-Amino-2-oxoethyl)-N-(carboxymethyl)-glycine; ADA
• Molecular Formula: C₆H₁₀N₂O₅
• Molecular Weight: 190.15
• Protein Sequence: G
• CAS Registry Number: 26239-55-4
• EC Number: 247-530-0
• SMILES: C(C(=O)N)N(CC(=O)O)CC(=O)O

Properties

• Melting point: 219 °C (dec.)
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

N-(2-Acetamido)iminodiacetic acid, commonly abbreviated as ADA, is a versatile compound that was discovered in the mid-20th century and used to improve diagnostic agents and biochemical tools. It is an aminopolycarboxylic acid that belongs to a class of compounds known for their ability to chelate metal ions, which is of great value in various scientific and industrial applications.

The molecular formula of ADA is C6H10N2O5. Its structure includes an acetylamino group attached to the iminodiacetic acid backbone. This configuration enables ADA to act as a strong chelator, binding metal ions through multiple coordination sites. This property is essential for its effectiveness in various biochemical and diagnostic applications. The compound also has the characteristic of high solubility in water, making it easy to use in aqueous solutions.

ADA is widely used as a chelator in biochemical research. Its ability to bind metal ions is used in enzyme assays and protein purification processes. By sequestering metal ions, ADA can prevent unwanted metal-catalyzed reactions and stabilize enzymes and proteins, ensuring accurate and reliable experimental results.

ADA derivatives have important applications in diagnostic imaging, especially in magnetic resonance imaging (MRI). When complexed with gadolinium, ADA forms a stable contrast agent that enhances the visibility of internal structures in MRI scans. This application has revolutionized medical imaging by providing clearer, more detailed diagnostic images.

In the pharmaceutical industry, ADA is used to enhance the stability and efficacy of certain drugs. Its chelating properties help protect active pharmaceutical ingredients from degradation caused by metal ions. This can extend the shelf life and effectiveness of drugs, ensuring better therapeutic outcomes.

ADA is used for the detoxification of metal ions in various industrial processes. For example, it is used in water treatment to remove heavy metals such as lead and mercury, making water safe to drink and reducing environmental pollution. Its strong binding affinity for metal ions makes it an effective agent for purifying water and other industrial wastewaters.

In agriculture, ADA is used as a chelating agent in fertilizers and soil conditioners. By binding essential metal nutrients, ADA helps improve their availability to plants, promoting better growth and yields. This application is particularly important in soils with high metal content, as ADA can mitigate the negative effects of metal toxicity on plant health.

While ADA is generally considered safe for use in a variety of applications, proper handling and use are essential to avoid potential risks. It is recommended that protective equipment be used when handling pure ADA as it may be irritating to the skin, eyes, and respiratory tract. Additionally, compliance with safety guidelines and regulations is important to ensure its safe and effective use in industrial and laboratory settings.

References

2023. Combined Thermodynamic, Theoretical, and Biological Study for Investigating N-(2-Acetamido)iminodiacetic Acid. Inorganic Chemistry, 62(39).
DOI: 10.1021/acs.inorgchem.3c02296

2016. Protein-directed self-assembly of a fullerene crystal. Nature Communications, 7.
DOI: 10.1038/ncomms11429

2015. Challenges of organic “cocrystals”. Science China Materials, 58(10).
DOI: 10.1007/s40843-015-0099-1