• 1. Synthesis and crystal structure of three silver(I) complexes with (S)-(+)-5-oxo-2-tetrahydrofurancarboxylic acid (S-Hothf?) and its isomeric forms (R-Hothf and R,S-Hothf?) showing wide spectra of effective antibacterial and antifungal activities. Chiral helical polymers in the solid state formed by self-assembly of the dimeric [Ag(othf?)]2 cores
  Kenji Nomiya,Satoshi Takahashi,Ryusuke Noguchi J. Chem. Soc. Dalton Trans. 2000 1343
• 2. Total synthesis of gonytolides C and G, lachnone C, and formal synthesis of blennolide C and diversonol
  Gangarajula Sudhakar,Shruthi Bayya,Vilas D. Kadam,Jagadeesh Babu Nanubolu Org. Biomol. Chem. 2014 12 5601
• 3. Synthetic manipulations of polyunsaturated fatty acids as a convenient strategy for the synthesis of bioactive compounds
  Anders Vik,Trond Vidar Hansen Org. Biomol. Chem. 2018 16 9319
• 4. Asymmetric total synthesis of (+)-swainsonine
  Soontorn Chooprayoon,Chutima Kuhakarn,Patoomratana Tuchinda,Vichai Reutrakul,Manat Pohmakotr Org. Biomol. Chem. 2011 9 531
• 5. Stereoselective synthesis of (?)-desethyleburnamonine, (?)-vindeburnol and (?)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Lactones Gamma butyrolactones
• Other Chemical additives Functional Additives
• Other Chemical Reagents

Comprehensive Analysis of (2S)-5-oxooxolane-2-carboxylic acid (CAS No. 21461-84-7): Properties, Applications, and Industry Trends

(2S)-5-oxooxolane-2-carboxylic acid (CAS No. 21461-84-7), also known as L-pyroglutamic acid or (S)-5-oxopyrrolidine-2-carboxylic acid, is a chiral organic compound belonging to the class of oxo carboxylic acids. This optically active molecule features a five-membered γ-lactam ring structure with a carboxylic acid functional group, making it a versatile building block in pharmaceutical synthesis and biochemical research. The compound's stereospecific configuration at the 2-position gives it unique biological activity, distinguishing it from its R-enantiomer counterpart.

Recent advancements in chiral synthesis have placed (2S)-5-oxooxolane-2-carboxylic acid at the forefront of peptide chemistry research. Its structural similarity to proline derivatives makes it valuable for designing conformationally constrained peptides, a hot topic in drug discovery for targeting G-protein coupled receptors. Analytical techniques such as HPLC chiral separation and circular dichroism spectroscopy are commonly employed to characterize this compound's purity and stereochemical integrity.

The pharmaceutical industry utilizes CAS 21461-84-7 as a precursor for nootropic compounds and cognitive enhancers, aligning with growing consumer interest in neuroprotective agents. Researchers are investigating its potential in mitochondrial function modulation, particularly in age-related cognitive decline studies. The compound's metal chelating properties also make it relevant in antioxidant formulations, addressing the booming market for anti-aging supplements.

In cosmeceutical applications, (2S)-5-oxooxolane-2-carboxylic acid demonstrates remarkable skin barrier enhancement properties. Its natural moisturizing factor (NMF) characteristics contribute to its inclusion in hyaluronic acid synergists formulations, responding to the global demand for dermocosmetic ingredients. The compound's keratolytic activity at optimal concentrations supports its use in mild exfoliation products, a trending category in clean beauty formulations.

From a green chemistry perspective, recent process optimizations have improved the atom economy of (2S)-5-oxooxolane-2-carboxylic acid synthesis. Biocatalytic routes using enantioselective enzymes have achieved impressive ee values (>99%), reducing the need for traditional chiral resolution methods. These advancements address the pharmaceutical industry's push toward sustainable manufacturing practices while maintaining regulatory compliance with ICH guidelines.

The analytical characterization of 21461-84-7 presents unique challenges due to its zwitterionic nature. Modern techniques combine LC-MS/MS with ion mobility spectrometry for accurate quantification in complex matrices. These methods are particularly valuable for metabolomic studies investigating the compound's endogenous role in glutathione metabolism, a subject of increasing research interest in oxidative stress management.

Industrial scale production of (2S)-5-oxooxolane-2-carboxylic acid has benefited from continuous flow chemistry innovations. The development of heterogeneous asymmetric catalysts has significantly improved production efficiency while reducing organic solvent waste. These process improvements have made the compound more accessible for high-throughput screening applications in drug discovery programs targeting neurodegenerative diseases.

Quality control specifications for CAS 21461-84-7 typically include rigorous testing for enantiomeric purity, residual solvents, and heavy metal content. Advanced QbD approaches (Quality by Design) are being implemented to ensure batch-to-batch consistency, particularly for GMP-grade material used in clinical trial formulations. These standards align with the pharmaceutical industry's increasing focus on quality metrics and regulatory expectations.

Emerging research suggests potential applications of (2S)-5-oxooxolane-2-carboxylic acid in biodegradable polymers. Its bifunctional nature allows incorporation into polyamide backbones, creating materials with interesting thermomechanical properties. This development intersects with the growing demand for bio-based plastics and sustainable packaging solutions across multiple industries.

The global market for chiral building blocks like 21461-84-7 continues to expand, driven by the pharmaceutical industry's need for stereochemically pure intermediates. Market analysts project particular growth in the Asia-Pacific region, where investments in specialty chemicals infrastructure are supporting local production capabilities. This geographic shift is reshaping traditional supply chain dynamics for fine chemicals.

Future research directions for (2S)-5-oxooxolane-2-carboxylic acid include exploration of its pharmacokinetic properties and potential as a prodrug moiety. The compound's blood-brain barrier permeability characteristics make it particularly interesting for CNS-targeted therapeutics development. These investigations align with broader trends in precision medicine and personalized healthcare solutions.

• 21461-86-9(2-Furancarboxylic acid,tetrahydro-2-methyl-5-oxo-, (2R)-)
• 178461-68-2(2-Furancarboxylic acid,tetrahydro-, 1-methylethyl ester, (R)- (9CI))
• 1126-51-8(Ethyl 5-oxooxolane-2-carboxylate)
• 4344-84-7(5-Oxotetrahydrofuran-2-carboxylic acid)
• 33019-03-3(2-Furancarboxylic acid,tetrahydro-5-oxo-, ethyl ester, (2R)-)
• 178461-70-6(2-Furancarboxylic acid,tetrahydro-, 1-methylethyl ester)
• 16874-34-3(Ethyl Tetrahydro-2-fuorate)
• 53558-93-3((2R)-5-oxotetrahydrofuran-2-carboxylic acid)
• 55094-96-7((R)-(-)-DIHYDRO-5-(HYDROXYMETHYL)-2(3H)-FURANONE)
• 178461-69-3(2-Furancarboxylic acid,tetrahydro-, butyl ester, (2S)-)