Ethyl L-thiazolidine-4-carboxylate hydrochloride, with the CAS number 86028-91-3, is a chiral sulfur-containing heterocyclic hydrochloride derivative, also known as (R)-Ethyl thiazolidine-4-carboxylate hydrochloride. Its molecular formula is C₆H₁₂ClNO₂S, and its molecular weight is 197.68 g/mol. It features a five-membered thiazolidine ring (containing one sulfur atom, one nitrogen atom, and three carbon atoms) with an ethyl ester group at the 4-position and a hydrochloride group, combining chiral properties, good chemical reactivity, and stability, making it widely applied in pharmaceutical synthesis, biochemistry research, and fine chemical production.
Physically, it appears as a white to off-white crystalline powder or granular solid. It has a melting point of approximately 108-112℃ and is highly soluble in water and common organic solvents such as methanol, ethanol, and dimethylformamide, while insoluble in non-polar solvents. It is optically active, with a specific rotation [α]²⁰/D of +85° to +90° (in water, c=1). It has low hygroscopicity and remains stable under normal temperature and pressure when stored properly, facilitating easy handling, storage, and formulation in various chemical and biological processes.
Chemically, its core thiazolidine ring, chiral center (at the 4-position), ethyl ester group, and hydrochloride group are the key features determining its properties. The thiazolidine ring is stable under neutral and weakly acidic conditions but may undergo ring-opening reactions under strong acid or strong alkali environments. The ethyl ester group enables ester hydrolysis reactions, while the hydrochloride group enhances its water solubility and reactivity. As a chiral building block, it is ideal for synthesizing compounds with specific stereoconfigurations, critical for pharmaceutical and fine chemical applications.
Its core applications focus on pharmaceutical synthesis and biochemistry research. In the pharmaceutical industry, it serves as a key intermediate for synthesizing antiviral drugs, antibacterial agents, peptide drugs, and chiral pharmaceuticals, especially compounds targeting infectious diseases and metabolic disorders. Its chiral structure ensures the stereoselectivity of final products, improving biological activity and reducing side effects.
In biochemistry research, it is used as a biochemical reagent for studying sulfur metabolism, enzyme activity, and chiral recognition, as well as an additive in cell culture media. Additionally, it is applied in fine chemical production to prepare chiral ligands and specialty chemicals. Safety-wise, it is generally recognized as safe under normal handling, with mild irritation potential upon direct contact. It should be stored in a sealed, cool, dry, and dark environment, away from oxidants, moisture, and high temperatures to prevent decomposition. With its unique chiral properties and versatile applications, it is an indispensable raw material in pharmaceutical and life science fields.
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