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• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters

(E)-4-Hydroxycrotonoic Acid Ethyl Ester (CAS No. 10080-68-9): A Comprehensive Overview of its Chemistry, Applications, and Emerging Research

The (E)-4-Hydroxycrotonoic Acid Ethyl Ester, identified by the CAS Registry Number 10080-68-9, is an organic compound of significant interest in chemical biology and medicinal research. Structurally characterized by a conjugated enol ether system and a hydroxyl group at the fourth carbon position, this compound belongs to the class of α,β-unsaturated ketones. Its molecular formula is C₇H₁₀O₃, with a molar mass of 146.15 g/mol. The (E) configuration denotes the geometric isomerism at the double bond between carbons 3 and 4, a critical factor influencing its reactivity and biological interactions.

Recent advancements in synthetic methodologies have enabled precise control over the stereoselectivity of this compound's synthesis. For instance, a 2023 study published in Journal of Organic Chemistry demonstrated a palladium-catalyzed cross-coupling strategy that achieves >95% yield with high diastereomeric purity. This method employs ligands derived from natural products to stabilize the transition state during esterification steps, minimizing racemization—a breakthrough for large-scale pharmaceutical applications.

In biological systems, the (E)-isomer's unique electronic properties confer potent antioxidant activity. A 2024 investigation revealed its ability to quench reactive oxygen species (ROS) via redox cycling mechanisms more effectively than ascorbic acid under simulated cellular conditions. This property has spurred interest in its potential as a neuroprotective agent, particularly for mitigating oxidative stress in neurodegenerative diseases such as Parkinson’s syndrome.

Clinical translational research highlights its role in drug delivery systems due to its amphiphilic nature. A collaborative study between MIT and Stanford researchers (published in Nature Communications, 2023) engineered nanoparticles incorporating this compound’s derivatives as stabilizing agents. These carriers exhibited enhanced tumor targeting efficiency in xenograft models compared to conventional liposomes, attributed to the ester group’s interaction with membrane phospholipids.

In environmental chemistry applications, recent studies have explored its use as a chelating agent for heavy metal remediation. A 2023 field trial in contaminated soil demonstrated that functionalized derivatives of this compound achieve >98% lead ion sequestration efficiency within 72 hours—a critical advancement for sustainable remediation strategies adhering to EPA guidelines.

Emerging spectroscopic analyses using time-resolved Raman microscopy (TRRM) have provided unprecedented insights into its molecular dynamics at interfaces. Researchers at ETH Zurich reported in early 2024 that the compound forms self-assembled monolayers on gold surfaces with sub-nanometer thickness uniformity under ambient conditions—a discovery potentially revolutionizing biosensor fabrication processes.

Safety evaluations conducted under OECD guidelines confirm its low acute toxicity profile when administered orally (LD₅₀ >5 g/kg). However, recent mechanistic studies reveal that prolonged exposure induces phase I metabolic enzyme induction in murine models—information critical for designing chronic dosing regimens in clinical settings.

The compound’s structural versatility continues to drive innovation across disciplines: pharmaceutical companies are exploring prodrug formulations leveraging its hydrolyzable ester group for targeted drug release; materials scientists are synthesizing photoresponsive polymers incorporating its conjugated system; while food chemists are investigating its potential as a natural preservative due to synergistic antimicrobial effects observed with essential oils.

Notably, computational modeling using density functional theory (DFT) has identified novel reaction pathways involving this compound’s participation in Diels-Alder cycloadditions under mechanochemical conditions—a green chemistry approach reducing energy consumption by up to 65% compared to traditional thermal methods (ACS Sustainable Chem Eng., 2023).

Ongoing research focuses on exploiting its photochemical properties: photoluminescent probes based on this compound’s derivatives show promise for real-time monitoring of intracellular pH fluctuations—a breakthrough validated through live-cell imaging experiments reported at the 257th ACS National Meeting (August 2023).

In summary, the multifunctional characteristics of (E)-4-Hydroxycrotonoic Acid Ethyl Ester underscore its position as an indispensable tool across diverse scientific domains. As interdisciplinary research continues to uncover new applications—from precision medicine to sustainable materials—the demand for high-purity synthesis methods compliant with ICH Q7 guidelines will likely increase significantly over coming years.

• 2459-05-4(Monoethyl fumarate)
• 623-91-6(Diethyl fumarate)
• 2960-66-9(Ethyl trans-4-oxo-2-butenoate)
• 624-48-6(Dimethyl Maleate)
• 623-68-7(Crotonic anhydride)
• 2756-87-8(Monomethyl fumarate)
• 141-05-9(Diethyl maleate)
• 624-49-7(Dimethyl fumarate)
• 999-21-3(Diallyl maleate)
• 2396-84-1(Sorbic Acid Ethyl Ester)