[(E)-octadec-9-enyl]azanium iodide
[CAS# 1802520-56-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: [(E)-octadec-9-enyl]azanium iodide
• Synonyms: Oleylammonium Iodide; (Z)-octadec-9-en-1-amine hydroiodide
• Molecular Formula: C₁₈H₃₈IN
• Molecular Weight: 395.41
• CAS Registry Number: 1802520-56-4
• SMILES: CCCCCCCC/C=C/CCCCCCCC[NH3+].[I-]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

[(E)-Octadec-9-enyl]azanium iodide is a quaternary ammonium compound consisting of a long-chain unsaturated hydrocarbon (octadec-9-enyl) covalently bonded to a positively charged nitrogen atom, with iodide as the counterion. This class of compounds, often referred to as long-chain alkylammonium salts, exhibits surfactant properties due to the combination of a hydrophobic hydrocarbon tail and a hydrophilic ammonium head, making them useful in a variety of chemical and industrial applications.

The compound’s discovery is part of the broader exploration of quaternary ammonium salts in the mid-20th century, initially investigated for their antimicrobial and detergent properties. The E-configuration of the double bond at the 9-position of the octadecyl chain imparts structural rigidity and influences the compound’s self-assembly behavior, interfacial activity, and biological interactions. Such structural features are critical in determining the compound’s physicochemical properties, including solubility, critical micelle concentration, and interactions with membranes or other amphiphilic systems.

In practical applications, [(E)-octadec-9-enyl]azanium iodide is primarily used as a surfactant, emulsifying agent, or phase-transfer catalyst. Its ability to reduce surface tension and stabilize emulsions makes it valuable in formulations such as cosmetics, personal care products, and detergents. Additionally, the quaternary ammonium moiety can facilitate ion exchange processes, enabling its use in synthetic chemistry for reactions that require transfer of reagents between immiscible phases. The iodide counterion can further influence solubility and reactivity, particularly in organic synthesis or catalysis.

The compound has also been explored for its antimicrobial and biocidal properties. Long-chain alkylammonium salts interact with microbial cell membranes through electrostatic attraction and hydrophobic insertion, leading to disruption of membrane integrity. This mechanism underlies their use as disinfectants, antiseptics, and preservative agents in both industrial and biomedical contexts. Structural variations, including unsaturation and chain length, are known to modulate efficacy, toxicity, and biodegradability.

Synthetically, [(E)-octadec-9-enyl]azanium iodide can be prepared via quaternization reactions, where the corresponding amine (oleylamine) is treated with methyl iodide or other suitable alkylating agents. Control over reaction conditions ensures selective formation of the quaternary ammonium salt and preservation of the E-configuration of the double bond. The compound is generally isolated as a crystalline solid or viscous oil, depending on purity and chain composition, and is compatible with various solvents used in industrial and laboratory settings.

In addition to its applications as a surfactant and antimicrobial agent, [(E)-octadec-9-enyl]azanium iodide has been employed in research on lipid bilayer systems, membrane mimetics, and nanostructured materials. Its amphiphilic nature facilitates the formation of micelles, vesicles, and monolayers, which are useful in studying molecular interactions, drug delivery systems, and nanotechnology-based assemblies. The compound’s ability to self-assemble and interact with other amphiphiles makes it a valuable model molecule in colloid and interface science.

Overall, [(E)-octadec-9-enyl]azanium iodide is a versatile quaternary ammonium salt with applications spanning surfactants, phase-transfer catalysis, antimicrobial formulations, and materials science. Its structural characteristics, including the long unsaturated alkyl chain and the positively charged nitrogen, underpin its physicochemical and biological properties, contributing to its utility in both industrial and research contexts.