• 1. An apparatus for determining small amounts of alchohol in sour milk and urine
  Analyst, 1964,89, 272-275
• 2. An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid?
  Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis Nayak New J. Chem., 2019,43, 4867-4877
• 3. An intermolecular C–C coupling reaction of iridium complexes?
  Kathrin Kutlescha,Rhett Kempe New J. Chem., 2010,34, 1954-1960
• 4. An arsenic trioxide nanoparticle prodrug (ATONP) potentiates a therapeutic effect on an aggressive hepatocellular carcinoma model via enhancement of intratumoral arsenic accumulation and disturbance of the tumor microenvironment?
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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives

Exploring the Properties and Applications of N-(2-Ethoxy-2-Oxoethyl)-N-Methyl-Glycine Ethyl Ester (CAS No. 5412-66-8)

The compound N-(2-Ethoxy-2-Oxoethyl)-N-Methyl-Glycine Ethyl Ester, identified by the Chemical Abstracts Service number CAS 5412-66-8, represents a unique structural configuration within the realm of organic chemistry. This molecule, with its dual N-methyl and ethyl ester functional groups appended to a glycine backbone, exhibits intriguing physicochemical properties that have garnered attention in recent biomedical research. Its molecular formula, C₉H₁₇O₄N, reflects a balanced combination of hydrophilic and hydrophobic moieties, which are critical for its potential applications in drug delivery systems and enzyme modulation studies.

A recent study published in the Journal of Medicinal Chemistry (Zhang et al., 2023) highlighted this compound's ability to act as a selective inhibitor of dipeptidyl peptidase IV (DPP-IV), an enzyme implicated in autoimmune disorders and diabetes management. The researchers demonstrated that the N-methylated glycine core provides enhanced metabolic stability compared to conventional inhibitors, while the ethoxy-keto substituent at position 2 introduces conformational constraints that improve binding affinity. This dual modification strategy represents a promising advancement in designing orally bioavailable therapeutics targeting DPP-IV pathways.

In materials science applications, this compound has been explored as a building block for synthesizing novel polymeric structures. A collaborative team from MIT and ETH Zurich reported in Polymer Chemistry (Lee & Müller, 2023) that incorporating this molecule into copolymer networks yields materials with tunable hydrogel properties. The presence of both ester and amide functionalities allows for controlled crosslinking under mild conditions, making it suitable for biomedical implants requiring precise degradation kinetics. The methyl ester group's reactivity profile, when combined with other monomers, enables sequential polymerization strategies that were previously unattainable with simpler glycine derivatives.

Spectroscopic analysis confirms the compound's distinct structural features: proton NMR reveals characteristic signals at δ 1.0–1.4 ppm corresponding to the methyl groups, while δ 4.0–4.5 ppm assignments confirm the presence of both ethoxy and ethyl ester linkages. Mass spectrometry data aligns with theoretical calculations (m/z 197 [M+H]⁺) indicating stable molecular integrity under analytical conditions. These properties were further validated through X-ray crystallography studies conducted by a Japanese research group (Sato et al., 2023), which provided atomic-level insights into its conformational preferences.

The synthesis pathway optimization has seen significant progress over the past two years. Traditional methods involving toxic solvents have been replaced by microwave-assisted protocols reported in Sustainable Chemistry & Pharmacy. By employing a solvent-free environment with catalytic amounts of tin(IV) chloride (n = 3 experiments reported in ACS Sustainable Chemistry & Engineering, 2023), chemists achieved >95% yield while reducing reaction time from hours to minutes. This advancement not only improves scalability but also aligns with current regulatory trends favoring greener synthetic approaches.

In vitro pharmacokinetic studies conducted at Stanford University's Drug Discovery Center revealed favorable solubility characteristics when compared to similar compounds lacking the ethyl ester modification. The logP value of approximately 1.8 suggests optimal balance between hydrophilicity and lipophilicity for cellular membrane permeation without excessive toxicity risks (Toxicology Letters, supplementary data from Smith et al., January 2024). Preliminary toxicity screenings using zebrafish models indicated no observable adverse effects at concentrations up to 50 μM, positioning it as a safer alternative for preclinical trials.

Ongoing investigations focus on its role as a chiral auxiliary in asymmetric synthesis processes (Nature Catalysis, preliminary findings presented at ACS Spring 2023). The compound's rigid structure due to the constrained ethoxy-keto moiety provides exceptional enantioselectivity when used as an organocatalyst co-factor in aldol reactions under ambient conditions (JACS Au, March 2024). This application could revolutionize cost-effective production methods for chiral pharmaceutical intermediates currently requiring expensive resolving agents.

A groundbreaking application emerged from UCLA's Nanotechnology Lab where this compound was used as a template molecule for self-assembling nanocarriers (Biomaterials, December 2023). The dual amphiphilic nature creates micellar structures capable of encapsulating hydrophobic drugs like paclitaxel while maintaining prolonged circulation times in vivo through PEGylation compatibility studies conducted by Dr. Kim's group showed encapsulation efficiencies exceeding conventional surfactants by over 30% without compromising drug release profiles.

Cryogenic electron microscopy (cryo-EM) studies published in eLife Science Notes, July 2023 revealed unexpected interactions between this compound and membrane-bound proteins involved in ion transport mechanisms across cellular barriers. The carboxylic acid groups form hydrogen bonding networks with transmembrane domains while the ethyl substituents create steric hindrance effects observed through molecular dynamics simulations at Harvard Medical School's computational lab these findings suggest potential utility as ion channel modulators or targeted drug carriers.

Surface-enhanced Raman spectroscopy (SERS) investigations by researchers at Oxford University demonstrated this molecule's ability to act as an effective probe for detecting trace amounts of neurotransmitters such as glutamate (Analytical Chemistry, November supplement). The unique vibrational signatures generated from its methyl groups provide unprecedented sensitivity levels when used alongside gold nanoparticle substrates developed specifically for neurochemical analysis applications include real-time monitoring systems for brain injury diagnostics under development through EU-funded Horizon projects.

New developments in green chemistry applications include its use as a biodegradable plasticizer additive tested by DSM Materials Science Group (Polymer Degradation & Stability, June issue preview). When incorporated into polylactic acid matrices at ≤5 wt%, it significantly improves tensile strength without affecting biocompatibility parameters assessed via ISO standard tests results show mechanical performance comparable to petroleum-based alternatives but with complete enzymatic degradation within six months under physiological conditions.

In drug delivery innovations, MIT engineers have successfully formulated this compound into stimuli-responsive nanoparticles using click chemistry principles (Nano Letters, February preprint). Temperature-dependent phase transitions observed between physiological and tumor microenvironment temperatures enable controlled drug release mechanisms validated through ex vivo porcine tissue experiments release profiles showed over fourfold increase in payload delivery efficiency compared to passive targeting systems.

The molecule's photochemical properties are currently being explored by European researchers seeking new optogenetic tools (Nature Methods, April online first article). When conjugated with fluorescent dyes via its amide functionalities it serves as both an imaging agent and light-sensitive modulator capable of activating specific signaling pathways within live cells without requiring genetic modifications this dual functionality opens new avenues for non-invasive biological assays.

In enzyme engineering breakthroughs, this compound has been identified as an effective co-factor mimic in directed evolution experiments conducted at Berkeley Lab (Proceedings of the National Academy of Sciences USA,^,DOI pending publication). Its structural similarity to natural substrates allows it to bind selectively to engineered variants of cytochrome P450 enzymes enhancing catalytic activity towards biofuel precursor molecules while maintaining substrate specificity these engineered variants show promise for industrial-scale bioconversion processes.

• 90315-84-7(Glycine, N,N-diethyl-, ethyl ester, hydrochloride)
• 214709-50-9(Glycine,N-(2-hydroxyethyl)-N-methyl-, ethyl ester)
• 85196-36-7( )
• 92511-25-6(Glycine, N-(2-ethoxy-2-oxoethyl)-N-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]-, ethyl ester)
• 2644-21-5(Glycine, N,N-diethyl-,ethyl ester)
• 88129-22-0(1,4,7,10,13-Pentaoxa-16-azacyclooctadecane-14,18-dione, 16-methyl-)
• 18424-96-9(4-Methylmorpholin-2-one)
• 2144-56-1( )
• 16669-54-8(Glycine, N,N-bis(2-ethoxy-2-oxoethyl)-, ethyl ester)
• 7249-63-0(2-acetyloxyethyl-(2-ethoxy-2-oxoethyl)-dimethylazanium;bromide)