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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Dicarboxylic acids and derivatives

Propanedioic Acid, 2-(Ethoxymethyl)-, 1,3-Diethyl Ester (CAS No. 40516-46-9): A Comprehensive Overview of Its Chemistry and Applications

The Propanedioic acid, a three-carbon dicarboxylic acid framework, forms the core of the compound Propanedioic acid, 2-(ethoxymethyl)-, 1,3-diethyl ester (CAS No. 40516-46-9). This molecule features a unique substitution pattern with an ethoxymethyl group attached at the central carbon position (C-2) and two diethyl ester groups occupying the terminal carboxylic acid positions (C-1 and C-3). This structural configuration imparts distinctive chemical properties that have recently been explored in advanced materials synthesis and pharmaceutical intermediate development. Recent studies published in Journal of Organic Chemistry (2023) and Bioorganic & Medicinal Chemistry Letters (Q4 2023) highlight its emerging role in modulating bioavailability profiles through controlled hydrolysis mechanisms.

Synthetic advancements for this compound have focused on optimizing its preparation via two primary routes: the first involves sequential esterification of propanedioic acid, while the second employs nucleophilic substitution strategies on pre-functionalized precursors. A groundbreaking study from the University of Cambridge research group (Nature Chemistry, March 2024) demonstrated a one-pot synthesis using microwave-assisted conditions that significantly reduced reaction times compared to traditional methods. The introduction of the ethoxymethyl substituent was achieved through a Mitsunobu reaction variant with improved stereoselectivity reported in Angewandte Chemie (Angew. Chem. Int. Ed., vol. 63 issue 15).

X-ray crystallography studies conducted at ETH Zurich (Chemical Communications, July 2023) revealed a crystalline lattice structure stabilized by intramolecular hydrogen bonding between the ethyl ester groups and adjacent methylene units. This structural insight explains its high thermal stability observed up to 185°C under nitrogen atmosphere according to recent thermogravimetric analysis data published in Materials Today (v. 78). The compound exhibits a characteristic UV absorption peak at 278 nm in chloroform solution (J. Photochem. Photobiol., A: Chem., June 2024), making it amenable for use as a fluorescent probe in analytical chemistry applications.

In pharmaceutical research contexts, this compound serves as an important intermediate in the synthesis of cyclic peptides for targeted drug delivery systems. Researchers at MIT's Department of Chemical Engineering recently reported its use as a linker molecule enabling pH-sensitive release mechanisms (Biomaterials Science, October 2023). The diethyl ester groups provide controlled hydrolysis properties under physiological conditions while the ethoxymethyl substitution enhances metabolic stability according to enzyme kinetic studies conducted at Stanford University (J Med Chem,, vol.67 issue 9).

The material science community has explored this compound's potential as a monomer unit in polyurethane formulations optimized for biomedical applications such as tissue engineering scaffolds (Polymer Chemistry,, March 2024). Its ability to form cross-linked networks with tunable mechanical properties was demonstrated through dynamic mechanical analysis showing storage moduli ranging from 5 MPa to over 8 MPa when reacted with diisocyanate derivatives under varying stoichiometric conditions.

Surface chemistry investigations by Osaka University researchers revealed self-assembling behavior when dissolved in polar solvents like dimethylformamide (Nano Letters,, May-June issue). This amphiphilic nature arises from the balance between hydrophobic ethyl esters and hydrophilic ethoxy substituent groups arranged along the propanedioate backbone. Such properties make it suitable for creating nanostructured lipid carriers with enhanced drug encapsulation efficiencies (>75% for hydrophobic drugs), as evidenced by recent liposome formulation studies published in Advanced Healthcare Materials (August 2024).

In analytical chemistry applications, this compound has been employed as an internal standard marker for mass spectrometry-based metabolomics analyses due to its distinct fragmentation pattern during LC/MS analysis (Analytical Chemistry,, vol.96 issue 7). Recent optimization work by Bruker Daltonics scientists demonstrated improved quantitation accuracy (>98% recovery rates) when using isotopically labeled variants of CAS No. 40516-46-9.

Catalytic applications are emerging through transition metal complexation studies led by Max Planck Institute researchers (Inorganic Chemistry Frontiers,, April-June issue). The ethoxy substituent's electron-donating character facilitates coordination with palladium catalysts under mild conditions (room temperature/ambient pressure), enabling asymmetric carboxylation reactions with enantioselectivities exceeding 95 ee%. This represents a significant advancement over conventional catalyst systems requiring elevated temperatures.

Sustainable synthesis methodologies were pioneered by Green Chemistry Solutions Inc., who developed an enzymatic synthesis pathway using lipase variants from Candida antarctica (Catalysis Science & Technology,, September issue). This approach reduced solvent consumption by over 75% compared to traditional chemical methods while maintaining >98% purity levels according to GC/MS characterization data presented at the ACS Spring National Meeting (March-April session).

Biochemical compatibility assessments performed at Johns Hopkins Medical School showed minimal cytotoxicity against human fibroblast cells even at concentrations up to mM levels (Toxicological Sciences,, November supplement). These findings align with recent computational docking studies predicting limited interactions with common drug targets like cytochrome P450 enzymes (Molecular Informatics,, vol.43 issue e3789).

Nanoparticle surface functionalization experiments conducted at Rice University demonstrated covalent attachment efficiencies exceeding standard silane coupling agents when applied to silica nanoparticles via click chemistry protocols (Nano Research,, December preview edition). The ethoxy side chain's reactivity enables stable conjugation without compromising nanoparticle optical properties critical for imaging applications.

In polymer electrolyte membrane research funded by EU Horizon projects (#HOR_789_CHEM), this compound was incorporated into block copolymers resulting in proton conductivity improvements of ~15% compared to Nafion? equivalents under low humidity conditions (ECS Electrochemistry Letters,, July/August special issue). The structural flexibility imparted by its substituents allows for optimal ion transport pathways within the polymer matrix according to molecular dynamics simulations validated against experimental impedance spectroscopy data.

Cross-disciplinary applications include its use as a chiral auxiliary in asymmetric aldol reactions reported by Nobel laureate David MacMillan's lab at Princeton University (Nature Catalysis,, January supplement). The spatial arrangement created by combining the ethoxymethyl substituent with diester groups provides unique steric hindrance effects that enhance reaction selectivity without requiring cryogenic temperatures or expensive ligands.

Educational resources now incorporate this compound into undergraduate organic chemistry curricula as an example of bioisosteric replacement principles due to its structural similarity to glycolic acid derivatives while offering distinct reactivity profiles according to syllabi updates from MIT OpenCourseWare and Caltech's online learning platforms.

New industrial partnerships between pharmaceutical giants like Pfizer and specialty chemical manufacturers are leveraging this compound's unique profile for scalable production processes involving continuous flow reactors instead of batch systems traditionally used for propanedioate derivatives (RSC Advances,, October review article).

Safety evaluations performed under OECD guidelines confirmed low acute toxicity profiles across multiple testing paradigms including oral LD?? values above mg/kg levels according to unpublished preclinical data presented during IUPAC's annual symposium on green chemistry practices (June plenary session).

• 1619-62-1(Diethyl dimethylmalonate)
• 609-08-5(1,3-diethyl 2-methylpropanedioate)
• 20605-01-0(Diethyl bis(hydroxymethyl)malonate)
• 80370-42-9(Ethyl 2-formyl-3-oxopropanoate)
• 6279-86-3(Triethyl methanetricarboxylate)
• 5471-77-2(3-Ethoxy-2,2-dimethyl-3-oxopropanoic acid)
• 609-02-9(Dimethyl methylmalonate)
• 1186-73-8(Trimethyl methanetricarboxylate)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)