2-(2-(2-Aminoethoxy)ethoxy)acetic acid
[CAS# 134978-97-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty acid
• Name: 2-(2-(2-Aminoethoxy)ethoxy)acetic acid
• Synonyms: H2N-PEG2-CH2COOH
• Molecular Formula: C₆H₁₃NO₄
• Molecular Weight: 163.17
• CAS Registry Number: 134978-97-5
• EC Number: 810-220-6
• SMILES: C(COCCOCC(=O)O)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*, 1.177
• Index of Refraction: 1.467, Calc.^*
• Boiling Point: 323.8±22.0 °C (760 mmHg), Calc.^*
• Flash Point: 149.6±22.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

2-(2-(2-Aminoethoxy)ethoxy)acetic acid, commonly referred to as AEAA, is a significant compound in the field of medicinal chemistry and biochemistry. This molecule features a unique structural configuration characterized by a branched ether chain and an amino group, which contribute to its diverse biological activities and applications.

The discovery of 2-(2-(2-Aminoethoxy)ethoxy)acetic acid can be traced back to research focused on amino acids and their derivatives. The exploration of amino acid analogs has been pivotal in understanding various biochemical pathways and developing therapeutic agents. The compound was synthesized to investigate its potential applications as a bioactive molecule, leading to further studies on its physiological effects and mechanisms of action.

One of the primary applications of AEAA is in the pharmaceutical industry, where it serves as a building block for the synthesis of various drug candidates. Its amino group allows for further modifications, enabling the design of molecules with improved efficacy and selectivity for specific biological targets. This feature is particularly valuable in the development of agents for treating neurological disorders, where compounds that can effectively cross the blood-brain barrier are essential.

In addition to its pharmaceutical applications, 2-(2-(2-Aminoethoxy)ethoxy)acetic acid is also explored for its role as a biochemical probe. Its structural similarity to natural amino acids allows researchers to utilize AEAA in studies examining protein interactions and enzyme activities. This property is particularly useful in elucidating the mechanisms of action of various biochemical processes and in the development of targeted therapies.

Another notable application of AEAA lies in its potential as a chelating agent. The amino group in the structure can interact with metal ions, making it suitable for use in coordination chemistry and in the development of metal-based therapeutic agents. This property has implications in both diagnostic and therapeutic applications, particularly in the treatment of metal overload conditions and in cancer therapy, where metal complexes can enhance the efficacy of chemotherapeutic agents.

Furthermore, the compound's stability and solubility in aqueous environments make it a suitable candidate for formulation in various delivery systems. This characteristic is essential in ensuring the bioavailability of therapeutic agents, particularly those intended for parenteral administration.

Ongoing research into 2-(2-(2-Aminoethoxy)ethoxy)acetic acid continues to unveil new applications and mechanisms of action, emphasizing its importance in drug discovery and development. As scientists explore the potential of amino acid derivatives in various therapeutic contexts, the relevance of AEAA in advancing medicinal chemistry remains significant.

In summary, 2-(2-(2-Aminoethoxy)ethoxy)acetic acid is a versatile compound with valuable applications in pharmaceutical chemistry, biochemical research, and coordination chemistry. Its discovery has paved the way for further exploration of amino acid derivatives in developing novel therapeutic agents and understanding biological processes.

References

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DOI: 10.1007/s00280-023-04550-7

2023. Elacestrant: a new FDA-approved SERD for the treatment of breast cancer. Medical Oncology (Northwood, London, England), 40(6).
DOI: 10.1007/s12032-023-02045-2

2023. Elacestrant: First Approval. Drugs, 83(6).
DOI: 10.1007/s40265-023-01861-0