N-[2-(Dodecyldisulfanyl)ethyl]acrylamide

N-[2-(Dodecyldisulfanyl)ethyl]acrylamide is a disulfide-containing acrylamide monomer that serves as a key synthetic building block in the construction of stimuli-responsive polymers, bioreducible drug delivery systems, and functional lipid-like materials. The acrylamide group in N-[2-(Dodecyldisulfanyl)ethyl]acrylamide enables free-radical polymerization and copolymerization with a wide range of vinyl monomers—including acrylates, methacrylates, and styrenics—facilitating the preparation of polymers with precisely positioned disulfide cross-links and pendant hydrophobic chains. The presence of the dodecyl tail in N-[2-(Dodecyldisulfanyl)ethyl]acrylamide imparts amphiphilic character, enabling the self-assembly of copolymers into micellar and nanoparticulate architectures suitable for encapsulating hydrophobic drug payloads or nucleic acid therapeutics. Recent literature demonstrates that acrylamides featuring disulfide bonds are employed as monomeric precursors in the combinatorial synthesis of bioreducible lipidoid libraries for messenger RNA (mRNA) and CRISPR guide RNA (sgRNA) delivery, where the acrylamide group undergoes Michael addition with amine-containing linkers to construct ionizable lipids optimized for lipid nanoparticle (LNP) formulations. The redox-sensitive disulfide bridge in N-[2-(Dodecyldisulfanyl)ethyl]acrylamide enables triggered degradation and controlled cargo release within the reducing intracellular milieu, a design principle that has been successfully exploited to enhance gene knockdown efficiency and minimize off-target toxicity. The predictable reactivity profile, combined with the compound’s dual functionality as both a polymerizable monomer and a lipid-anchoring moiety, has established N-[2-(Dodecyldisulfanyl)ethyl]acrylamide as a versatile platform molecule in the fields of polymer chemistry, nanomedicine, and targeted therapeutic delivery.

Product Parameters

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Quality Assurance at Cosperpharm

Each batch undergoes:

● Gas chromatography (GC) – purity ≥97.0%

● Non‑aqueous titration – purity ≥97.0%

● Refractive index – confirmatory analysis

● ¹H NMR – structural verification

● Appearance – colorless to light yellow to light orange clear liquid

A comprehensive COA, MSDS (with full GHS information), and certificate of origin accompany every shipment.

FAQ

Q1: How should N-[2-(Dodecyldisulfanyl)ethyl]acrylamide be stored?

A: For long-term integrity, store at –20 °C in a tightly sealed container under an inert atmosphere of nitrogen or argon, protected from light and moisture. The acrylamide group is susceptible to free-radical polymerization, and the disulfide bond may undergo exchange reactions or reductive cleavage. Allow the sealed container to equilibrate to ambient temperature before opening to prevent moisture condensation.

Q2: What is the significance of the disulfide bond in this compound?

A: The disulfide (-S-S-) bridge is a redox-responsive linker that remains stable under extracellular oxidizing conditions but undergoes rapid cleavage in the reducing intracellular environment (1–10 mM glutathione). This property enables the design of delivery systems that selectively degrade and release therapeutic cargo within target cells. Disulfide-based self-immolative linkers are among the most attractive linkers for developing polymers suitable for delivering drugs and imaging agents.

Contact us

If you wish to evaluate N-[2-(Dodecyldisulfanyl)ethyl]acrylamide before placing a full order, milligram-scale samples are available for polymerization feasibility studies, copolymerization screening, and system suitability testing. Simply mention your interest when you reach out.