Sodium 5-Oxo-Dl-Prolinate: An In-Depth Commentary

Historical Development

Industries first became interested in Sodium 5-Oxo-Dl-Prolinate as researchers started digging into the cyclic forms of amino acid derivatives in the mid-20th century. Scientific curiosity about proline derivatives and their salt forms sparked the earliest patents, and labs exploring ways to stabilize compounds with active carboxyl or amine groups soon came across this sodium salt. Early work often centered on the compound’s role as a model system for peptide research. Since then, sodium 5-oxo-DL-prolinate has steadily found new homes in different fields—both in theory and in practice. The path from bench-scale synthesis to inclusion in product libraries shows how this compound found respect in chemical and biotech circles.

Product Overview

Sodium 5-Oxo-Dl-Prolinate comes in crystalline or powder form. The compound serves as a functional building block for various chemical syntheses, admired for its stable nature and compatibility in aqueous and non-aqueous systems. Producers of peptide intermediates, pharmaceutical research teams, and engineers working on biodegradable chelating agents regularly turn to this salt. Its popularity stems from its clear performance in technical applications, including its role as a reactant and process aid.

Physical & Chemical Properties

This compound carries a molecular formula of C5H6NNaO3, a molecular weight around 155.1 g/mol, and presents as a white or off-white solid. Sodium 5-oxo-DL-prolinate dissolves easily in water, offering a neutral to slightly basic solution, thanks to the sodium ion. Its melting point sits above 200°C (decomposition) and it remains fairly stable under typical laboratory conditions. Chemical structure modeling shows a five-membered lactam ring, which resists simple hydrolysis and stands up to short bursts of high pH without breaking down. All these features mark the compound as a practical intermediate for chemists who need reliability batch after batch.

Technical Specifications & Labeling

Manufacturers test for purity above 98%, verified using chromatography or titration. Impurity profiles include limits for proline, sodium chloride, and other close relatives. Containers ship labeled with CAS number 7704-72-5, product code, batch number, net weight, and safety information such as hazard symbols for skin and eye irritation based on classification. Safety Data Sheets accompany each shipment. I’ve seen plenty of suppliers meeting up with European, US Pharmacopeial, and REACH standards, especially for research or pilot plant quantities. The details, including water content by Karl Fischer and particle sizing, turn out crucial when researchers aim for scale-up.

Preparation Method

Industrial production often starts from 5-oxoproline (also called pyroglutamic acid), with direct neutralization by sodium hydroxide in water, followed by careful crystallization and drying. I’ve spoken to technicians who highlight the need for temperature control during crystallization to avoid co-precipitation with sodium chloride, which affects downstream purity. Filtration and drying processes may run under vacuum to prevent hydrolysis or racemization. Labs may adapt this process—for example, choosing lyophilization for smaller, more sensitive batches. Firms moving toward greener chemistry try to minimize solvent or energy use, sometimes integrating in-line purification to reduce waste.

Chemical Reactions & Modifications

As a five-membered lactam sodium salt, it participates readily in nucleophilic substitutions, ring-opening reactions, and amidation. Researchers have turned to sodium 5-oxo-DL-prolinate to build more complex peptidomimetics, modify surfaces for biomedical devices, or test enzyme activity with cyclic substrates. Functionalization at the alpha-carbon allows for the creation of novel derivatives—advancing fields as diverse as human health and polymer development. Concerns about side reactions—for example, epimerization or decarboxylation—crop up, yet careful reaction monitoring keeps the process on track for most users. Chemists appreciate its balance of reactivity and predictability.

Synonyms & Product Names

Sodium pyroglutamate, sodium 5-oxo-L-prolinate (or DL-prolinate for the racemic mixture), and sodium PID—these crop up in literature and product sheets. Sigma-Aldrich, Tokyo Chemical Industry, and other chemical distributors offer it under proprietary names, generally cross-referenced to the CAS number. Some suppliers shorten the name to Na-pyroglutamate or use foreign language equivalents, leading to a patchwork of synonyms depending on region and supplier. Users often double-check labeling to prevent mix-ups, especially when quality matters.

Safety & Operational Standards

Handling runs under standard chemical hygiene rules: gloves and eye protection, good ventilation, and prompt cleanup if spills occur. MSDS sheets point out minor skin and eye irritation but generally no systemic toxicity at expected exposure levels—although chronic effects deserve more attention. Workers avoid inhalation of dust, and storage happens in well-sealed containers, away from moisture and direct sunlight. Disposal adheres to local environmental regulations, typically involving dilution and neutralization before release. As someone who’s seen accidents from poor labeling, I can’t overstate the value of clear hazard communication and routine training on spill response.

Application Area

This compound shows up in diverse environments: peptide synthesis, pharmaceutical intermediates, cosmetics, and food ingredient research. Scientists studying glutamatergic neurotransmission use sodium 5-oxo-DL-prolinate as a model substrate in enzymatic assays. In the cosmetics industry, it features as a humectant and skin-conditioning agent, taking advantage of its affinity for water and skin. Food technologists keep it handy when researching flavor enhancers, while plant biologists explore its function as a stress modulator in crop science. The sheer range of applications reflects both the compound’s chemical stability and biological compatibility.

Research & Development

R&D labs keep finding ways to tune derivatives—shifting from academic curiosity to real-world solutions. Recent work centers on modified versions for targeted drug delivery, given the compound’s ability to blend into biological pathways. Some projects aim to attach therapeutic agents or imaging markers to the lactam ring, improving selectivity and reducing adverse reactions. Efforts to boost process greenness, like biocatalytic production from renewable sources, gain traction as regulatory pressure mounts. Now and then, interdisciplinary teams combine physical chemistry, pharmacology, and engineering to open new avenues—each project a bet on the compound’s untapped potential.

Toxicity Research

Studies so far suggest low toxicity in mammals, both in acute and chronic settings, which explains why regulatory agencies show limited concern at standard industrial concentrations. Oral and dermal LD50 figures land comfortably high in rodents, but gaps in knowledge remain, especially with respect to long-term exposure and environmental buildup. Scientists call for better epidemiological data and more nuanced models of how sodium 5-oxo-DL-prolinate behaves in soil and water. Environmental researchers track its degradation for any trace-level impact on groundwater or aquatic systems—not just out of caution, but out of lessons learned from past chemical releases.

Future Prospects

As the life sciences push for more sustainable ingredients and greener manufacturing, demand for versatile, low-toxicity chemicals like sodium 5-oxo-DL-prolinate won’t slow down. The compound’s use as a chemical precursor gives it staying power in pharma and agriculture. Next-generation synthesis routes—perhaps enzyme-catalyzed or powered by renewable energy—could reshape its production economics. If researchers unlock more about its role as a biochemical modulator, sodium 5-oxo-DL-prolinate could show up in more functional foods or medical devices. As a chemical I’ve encountered both on the benchtop and in large-scale setups, it stands as a quiet, reliable performer ready for whatever challenges industry and science send next.




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Sodium 5-Oxo-Dl-Prolinate
Sodium 5-Oxo-Dl-Prolinate
Sodium 5-Oxo-Dl-Prolinate