Epalrestat (Z, Z)-Isomer
Product Code：E022004
English Name：Epalrestat (Z, Z)-Isomer
English Alias：2-((Z)-5-((Z)-2-methyl-3-phenylallylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid
CAS No.：124782-63-4
Molecular Formula：C₁₅H₁₃NO₃S₂
Molecular Weight：319.4
High-Purity Reference Standard：Confirmed by HPLC (≥99.0%), NMR (1H, 13C), HRMS, and X-ray crystallography for stereostructure, suitable for cis-isomer impurity analysis of Epalrestat.
Stability Assurance：Stable for 36 months at -20℃ under light-protected, sealed storage; degradation rate <0.1% in methanol-water solution within 6 months.
Quality Control Testing：Used for UPLC-MS/MS detection of (Z,Z)-isomer in Epalrestat API and formulations, controlling impurity content to meet ICH Q3A standards (≤0.1%).
Process Optimization Research：Monitors cis-isomer formation during Epalrestat synthesis, reducing generation by >50% by adjusting condensation temperature (e.g., 0-5℃) and reaction time.
Method Validation：Serves as a chiral standard for developing isomer separation methods, verifying UPLC resolution (≥3.0) and LOD (0.005 ng/mL).
Epalrestat, an aldose reductase inhibitor, is used for treating diabetic neuropathy. The (Z,Z)-isomer, as a cis-impurity, may originate from stereoselective side reactions during allylation in synthesis or configuration conversion under high temperature and acidic conditions. Its thioxothiazolidine ring and phenyl structure may affect drug stability and efficacy. With stricter EMA requirements for chiral impurity control, studying such cis-impurities is key to ensuring drug quality.
Detection Technology：UPLC-MS/MS with Chiralpak IA column (1.7μm) and n-hexane-ethanol (85:15) gradient elution achieves separation within 4.5 minutes, with LOD of 0.002 ng/mL for trace chiral impurity analysis.
Formation Mechanism：Formed by reaction of 2-methyl-3-phenylacrolein with thioxothiazolidinone under alkaline conditions (e.g., sodium carbonate catalysis). Using enzymatic catalysis (e.g., lipase) or asymmetric catalysis reduces cis-impurity formation by >80%.
Safety Evaluation：In vitro cytotoxicity shows IC₅₀ of 182.5 μM against HepG2 cells (Epalrestat IC₅₀=12.6 μM), with low toxicity but requiring ≤0.1% limit. Accelerated stability testing is ongoing to monitor configuration conversion rates under different pH conditions.
This product is intended for laboratory use only!
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