25527-70-2

Usage

Chemical class

Quaternary ammonium compounds

Explanation

1-Dodecyl-3-hydroxyquinuclidinium bromide is a compound with a positively charged nitrogen atom, which is a characteristic feature of quaternary ammonium compounds.

Explanation

1-Dodecyl-3-hydroxyquinuclidinium bromide is widely used as a surfactant to reduce surface tension in solutions and as an antimicrobial agent to inhibit the growth of microorganisms.

Explanation

The positive charge of the compound allows it to interact with the negatively charged cell membranes, disrupting their structure and ultimately inhibiting the growth of microorganisms.

Explanation

The presence of both hydrophobic and hydrophilic components in the molecule allows it to interact with both water and oil, making it an effective surfactant.

Explanation

The amphiphilic nature of 1-Dodecyl-3-hydroxyquinuclidinium bromide enables it to aggregate into micelles, with the hydrophobic alkyl chains pointing inward and the hydrophilic quinuclidine rings pointing outward.

Explanation

Due to its surfactant and antimicrobial properties, 1-Dodecyl-3-hydroxyquinuclidinium bromide is a valuable ingredient in various consumer products, including cosmetics and personal care items, as well as pharmaceutical formulations.

Explanation

Researchers are exploring the possibility of using 1-Dodecyl-3-hydroxyquinuclidinium bromide as a component in drug delivery systems to improve the efficacy of medications and as a novel antibacterial agent to combat resistant bacteria.

Common uses

Surfactant and antimicrobial agent

Mechanism of action

Disrupts cell membranes and inhibits microorganism growth

Amphiphilic nature

Long hydrophobic alkyl chain and hydrophilic quinuclidine ring

Micelle formation

Capable of forming micelles in solution

Industrial and pharmaceutical applications

Used in cosmetics, personal care products, and pharmaceutical formulations

Potential uses

Drug delivery systems and antibacterial agent

Upstream product

• 143-15-7 1-dodecylbromide 
• 1619-34-7 3-quinuclidinol 

Relevant academic research and scientific papers

Discovery of novel quaternary ammonium compounds based on quinuclidine-3-ol as new potential antimicrobial candidates

Quaternary ammonium compounds (QACs) are amphiphilic molecules displaying a broad-spectrum of antibacterial activity. QACs are commonly used antiseptics in industrial, home and hospital settings. Given the emergence of the QAC-resistant bacteria, there is an urgent need to design new QACs with good antimicrobial activity, able to escape the host resistance mechanism. Therefore, a series of QACs derived from quinuclidine-3-ol and an alkyl chain of variable length (QOH-C3 to -C14), was designed and synthesized. The antimicrobial potential of the new monoquaternary QACs was surveyed against seventeen strains of emerging food spoilage and pathogenic microorganisms, including clinical multidrug-resistant ESKAPE isolates. The QOH-C14 proved to have the strongest antimicrobial activity. It was highly active against all pathogens tested, particularly against the Gram-positive bacteria with minimal inhibitory concentrations (MICs) ranging from 0.06 to 3.9 μg/mL, and fungi exerting the MIC90 between 0.12 and 3.9 μg/mL. The potency of QOH-C14, confirmed that alkyl chains are an important part of the structure with their lengths playing a critical role in bioactivity of these compounds. The atomic force microscopy images show the disruption of a cell membrane upon the treatment with QOH-C14. These results were additionally confirmed by flow cytometry and fluorescence microscopy. A relatively low toxicity toward healthy human cells underline that QOH-C14 has a potential as new QAC antimicrobial candidate.