2-Propenoic acid, 2-(dodecyldithio)ethyl ester

2-Propenoic Acid, 2‑(Dodecyldithio)ethyl Ester (CAS 1624618‑10‑5) is a specialized long‑chain acrylate monomer designed for advanced drug delivery systems requiring maximum lipophilicity and redox‑responsive release. 2-Propenoic Acid, 2‑(Dodecyldithio)ethyl Ester features a reducible disulfide bond that enables triggered intracellular payload release, making it particularly valuable for nucleic acid delivery and targeted drug release applications. Additionally, 2-Propenoic Acid, 2‑(Dodecyldithio)ethyl Ester can be polymerized into highly stable bioreducible polymers that degrade under reducing conditions, releasing encapsulated therapeutics specifically at target sites. Moreover, 2-Propenoic Acid, 2‑(Dodecyldithio)ethyl Ester serves as a superior precursor for long‑chain cationic lipids used in siRNA and mRNA delivery, where the extended C₁₂ alkyl chain provides maximum nanoparticle stability and extended circulation half‑life. With a molecular weight of 332.56 g/mol and supplied as a liquid, 2-Propenoic Acid, 2‑(Dodecyldithio)ethyl Ester is the preferred choice for researchers requiring maximum hydrophobicity in their redox‑responsive lipid formulations.

Product Parameters

Synthetic Route

Synthesis from Acrylic Acid and Dodecyl Disulfide via Esterification

2-Propenoic Acid, 2‑(Dodecyldithio)ethyl Ester can be synthesized through an analogous route to the shorter‑chain homologs:

Step 1 — Preparation of 2‑(dodecyldithio)ethanol: Dodecyl mercaptan (C₁₂H₂₅SH) is oxidized in the presence of 2‑mercaptoethanol (HS‑CH₂CH₂OH) to form the mixed disulfide 2‑(dodecyldithio)ethanol.

Step 2 — Esterification: The resulting 2‑(dodecyldithio)ethanol is esterified with acrylic acid in the presence of a coupling agent such as DCC or EDC, or via acid‑catalyzed Fischer esterification, to yield 2-Propenoic Acid, 2‑(Dodecyldithio)ethyl Ester.

Step 3 — Purification: The crude product is purified by column chromatography or distillation to achieve target purity (≥95%).

Application Scenarios

Long‑Chain Cationic Lipid for siRNA Delivery

Acts as a precursor for C₁₂‑based cationic lipids used in siRNA delivery; the extended alkyl chain maximizes LNP stability and circulation half‑life.

mRNA Delivery Vehicle Development

Disulfide‑containing lipids derived from this monomer are investigated as components of liposomal delivery vehicles for mRNA expression; the C₁₂ chain provides extended circulation.

Bioreducible Polymer Synthesis

Serves as a monomer for synthesizing highly stable bioreducible polymers; the disulfide bond imparts redox‑responsiveness for triggered drug or gene release.

Stimuli‑Responsive Hydrogels

Incorporated into hydrogels that respond to reducing environments, enabling controlled release of encapsulated therapeutics in sites with elevated glutathione levels.

pDNA Delivery Lipid Nanoparticles

Used in formulating lipid nanoparticles for plasmid DNA delivery; the long C₁₂ chain contributes to nanoparticle stability and mucus permeability (analogous to the C₁₀ analog).

Targeted Drug Delivery Systems

The reducible disulfide bond enables triggered drug release specifically after cellular uptake, making it valuable for cancer and gene therapy applications.

Gene Therapy Research Provides a long‑chain redox‑responsive linker platform for developing gene delivery systems with efficient cytosolic release.

Structure‑Activity Relationship Studies

Useful for comparative studies investigating the effect of alkyl chain length (C₈ vs. C₁₀ vs. C₁₂) on LNP stability, transfection efficiency, pharmacokinetics, and cytotoxicity.

Product Quality Assurance

Cosperpharm has established a comprehensive quality assurance system for 2-Propenoic Acid, 2‑(Dodecyldithio)ethyl Ester that meets the rigorous expectations of pharmaceutical intermediate manufacturing and gene delivery research applications:

Thorough analytical characterization. Each batch undergoes multi‑technique analytical release testing: HPLC purity (≥95%), appearance verification (colorless to light‑yellow liquid), water content determination (Karl Fischer), residual solvent analysis (GC), and identity confirmation by ¹H NMR.

Full batch traceability with retention samples. From raw material procurement through synthesis, purification, stabilization, and final packaging, every step is fully documented and traceable. Each batch receives a unique lot number with sufficient retention samples maintained in accordance with Cosperpharm quality procedures.

Stability monitoring program. Cosperpharm conducts ongoing stability studies under recommended storage conditions (–20 °C, sealed under inert atmosphere). Stability summaries are updated regularly, with full data packages available to support customer research and regulatory submissions.

Documentation ready for regulatory submission. Every shipment includes a Certificate of Analysis (COA) with batch‑specific purity and characterization data, a Material Safety Data Sheet (SDS), and customs documentation for international delivery. For customers developing LNP‑based therapeutics, Cosperpharm provides DMF‑ready documentation packages, method validation reports, stability data, and custom quality agreements upon request.

Customer‑initiated quality audits. Qualified customers are welcome to audit Cosperpharm‘s manufacturing, quality control, and documentation facilities. Please contact our regulatory team to schedule an audit.

Contact Us

Ready to advance your LNP formulation with 2-Propenoic Acid, 2‑(Dodecyldithio)ethyl Ester? Cosperpharm is your trusted source for high‑purity disulfide‑containing monomers with comprehensive documentation and flexible supply options. Contact us today to request a quote, obtain a Certificate of Analysis, or discuss custom synthesis and packaging requirements. Our dedicated customer support team is ready to assist with product specifications, regulatory documentation, and shipping coordination. From early‑stage formulation screening to commercial manufacturing, we’re here to support your success.