Tetraalkylammonium salt - Hydrocarbon derivative - Organic chloride salt - Organic salt - Amine - Organic cation - Aliphatic acyclic compound
Descrizione
This compound belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
582.500 g/mol
XLogP3
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
32
Exact Mass
581.567 Da
Monoisotopic Mass
581.567 Da
Topological Polar Surface Area
0.000 Ų
Heavy Atom Count
40
Formal Charge
0
Complexity
459.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
2
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
2
Covalently-Bonded Unit Count
2
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No vendor‑validated application protocols are provided for this SKU.
General guidance (research, non‑validated):
For liposome formation, see the Reaction Conditions tab for common thin‑film hydration or ethanol‑injection approaches.
For surface coating, prepare 0.1–5 mg/mL solutions in alcohol/water and apply by dip‑ or spin‑coating; rinse with alcohol/water to remove loosely bound material, then characterize by contact angle and zeta potential.
Users should optimize concentrations, temperatures, and mixing methods for their specific system and analytical endpoints.
Biological Roles
This compound is not a natural metabolite; it is a synthetic cationic lipid/surfactant. The points below summarize behavior observed for cationic dioleyl ammonium species in research contexts (general literature; not item‑specific):
Membrane interactions: Strongly adsorbs to negatively charged lipid bilayers and biomembranes via electrostatics and hydrophobic insertion of the oleyl chains, often increasing membrane curvature and permeability at sufficient loadings.
Polyanion complexation: Forms electrostatic complexes (polyplexes/lipoplexes) with nucleic acids and other polyanions; complex stability depends on charge ratio (N+/P−), ionic strength, and helper lipids.
Self‑assembly: Dioleyl chains promote fluid bilayers (low gel–fluid transition) and support formation of small unilamellar vesicles on sonication or extrusion.
Protein interactions: Cationic surfactants can denature proteins by binding to acidic residues and disrupting hydrophobic cores; exploitation requires careful optimization to avoid loss of activity in biochemical assays.
Cytocompatibility (qualitative): Activity follows a typical cationic surfactant profile—membrane perturbation increases with dose. Application‑specific titration and appropriate controls are essential.
No medical or clinical claims are made. For cell‑based research, tailor conditions (dose, exposure time, serum content, helper lipids) to minimize nonspecific membrane disruption while achieving the desired complexation or delivery behavior.
Buffer Applications
Dioleyldimonium chloride is not a buffering agent and does not establish a defined pH range. It is therefore not typically used to prepare classical buffer systems.
Practical note: In aqueous media it may be dispersed into pre‑made buffers (e.g., phosphate, HEPES) to form micelles or vesicles. Buffer ionic strength and pH modulate aggregation and polyanion complexation but the compound itself provides no buffering capacity.
For buffer formulation guidance, refer instead to appropriate acid/conjugate base systems and then incorporate this surfactant as a functional additive if needed.
Green Alternatives
Consideration of greener choices depends on the application (surfactancy vs. templating vs. extraction).
Environmental profile (general): Long‑chain quaternary ammonium compounds can be persistent and are typically toxic to aquatic organisms. Unsaturated chains (oleyl) may improve biodegradability compared to fully saturated analogs but do not eliminate ecotoxicity concerns.
Potential alternatives (application‑dependent):
Biobased/biodegradable cationics ("esterquats"): Incorporate hydrolyzable ester linkages in the hydrophobe, improving biodegradation. Tradeoff: lower hydrolytic stability in aqueous formulations, especially at extreme pH.
Zwitterionic or betaine surfactants: Lower aquatic toxicity and good mildness; however, they lack strong cationic charge needed for binding to anionic substrates or nucleic acids.
Choline‑based lipids: Quaternary ammonium headgroups derived from choline can offer better toxicological profiles in some contexts; performance must be validated.
Polymeric cationic stabilizers (e.g., PDADMAC): Water‑soluble, effective flocculants; not drop‑in replacements for bilayer formation.
Comparison highlights (general):
Performance: Dioleyl quats excel at forming stable bilayers/lipoplexes; many greener options are weaker complexants for polyanions.
Process: Alcohol‑water systems and supercritical CO2 (for film casting/delipidation) can reduce chlorinated solvent use with this material.
Where possible, design formulations to minimize dose, enable recovery, and prevent release to wastewater. Evaluate alternatives via biodegradation testing, aquatic toxicity screening, and performance metrics relevant to your use.
Pharmaceutical Uses
No pharmacopeial designation or excipient grade is specified for this item; it is supplied for research use only.
General research/formulation context for cationic dioleyl ammonium compounds (non‑clinical, no therapeutic claims):
Cationic lipid component in experimental liposomal or lipid‑nanoparticle systems to promote electrostatic complexation with anionic cargos (e.g., nucleic acids, anionic peptides) and to modulate zeta potential.
Mucoadhesion and surface binding: Positive surface charge can increase adhesion to negatively charged substrates; requires balancing with biocompatibility concerns.
Topical/dermal research: Investigated as a penetration‑enhancing surfactant in model systems; dosing and irritation potential must be assessed.
Controlled release matrices: Incorporated into polymer films or hydrogels to adjust ion‑exchange interactions with anionic drugs in vitro.
If regulatory development is anticipated, select materials with defined excipient grades and full impurity/toxicology packages. For this SKU, consult the CoA for residual solvents, chloride content, peroxide/oxidation markers, and perform in‑house biocompatibility screening appropriate to your application.
Physical Properties
Item-specific numerical specifications (BP, MP, density, refractive index, water/peroxide/metal limits, UV cutoff) are not provided for this SKU.
Appearance (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
General/literature characteristics for dioleyl quaternary ammonium surfactants (informative, not item specifications):
Physical state: Typically a waxy solid or highly viscous paste at ambient temperature; may soften above room temperature due to long unsaturated chains.
Amphiphilicity: Cationic headgroup with two C18:1 tails promotes self‑assembly (micelles, vesicles, bilayers) in water above a formulation‑dependent CMC; exact CMC varies with ionic strength and co‑solvents.
Solubility (literature):
Water: Low solubility as monomer; dispersible as colloids/micelles; enhanced by alcohol/water mixtures or by adding co‑lipids.
Organic solvents: Good solubility in alcohols (MeOH, EtOH, i‑PrOH), chlorinated solvents (CH2Cl2, CHCl3), ethers (THF), and hydrocarbons/aromatics when warmed.
LogP: Very high (expected for dialkyl surfactants); exact value not established here.
pKa: Not applicable (permanently charged quaternary ammonium).
For process or QC needs (e.g., exact softening point, residual solvent, chloride content), consult the CoA/Spec Sheet for this lot.
Quality and Grades
Grade/Purity (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting grade information (general):
Research grade materials are suitable for R&D, method development, and formulation screening. Where offered, HPLC or UV‑transparent grades limit nonvolatile residues and UV‑active impurities for analytical work; biochemical grades may control bioburden and endotoxin.
Stabilizers: Quaternary ammonium surfactants typically do not require added stabilizers, but unsaturated chains (oleyl) can slowly oxidize; presence/absence of antioxidants (e.g., BHT) is item‑specific—verify on CoA if relevant to your application.
Impurity considerations: Residual solvents, free amine precursors, chloride content, moisture, and iodine value (degree of unsaturation) can impact performance in self‑assembly and transfection‑type research.
Recommendations:
Request the CoA for lot‑specific assay, residual solvents, moisture, and peroxide/oxidation markers. Where UV work is planned, ask for UV absorbance trace in relevant solvents.
For reproducible colloid or liposome behavior, control the thermal history and verify the material’s softening profile and moisture content per the lot documentation.
Reaction and Applications
This compound’s main value is as a cationic surfactant/lipid for self‑assembly and interfacial processes rather than as a stoichiometric reagent.
Representative research applications (general/literature):
Cationic liposomes/vesicles: Forms bilayers and lipoplexes in combination with helper lipids (e.g., cholesterol, DOPE). Used for studying nucleic acid complexation, membrane biophysics, and colloid stabilization in research settings.
Interfacial stabilization: Emulsifier for water‑in‑oil or oil‑in‑water systems; promotes adsorption to negatively charged surfaces (silica, clays, some oxides) for coating and dispersion control.
Colloid and nanoparticle synthesis: Serves as a soft template or capping agent for inorganic nanoparticle growth in reverse micelles or microemulsions.
Phase‑transfer/ion pairing: As a lipophilic cation, can extract anionic species from water into organic phases; less conventional than small tetraalkylammonium salts but effective for bulky/hydrophobic anions.
Antimicrobial surface research: Quats are frequently investigated for contact‑active cationic coatings on polymers and textiles (lab studies; no claims of biocidal approval implied).
Practical notes:
Hydration above the material’s softening temperature eases vesicle formation.
Ionic strength and pH of the aqueous phase strongly influence aggregate size and zeta potential.
Avoid mixing with anionic detergents, which forms inactive ion‑pair precipitates.
For method transfer or scale‑up, characterize aggregate size (DLS), zeta potential, and chloride content lot‑by‑lot.
Reaction Conditions
No item‑specific tested reaction conditions are provided. The following are general, literature‑based practices for using dioleyl quaternary ammonium surfactants in common research workflows:
Liposome/lipoplex preparation:
Solvent casting: dissolve the lipid in CHCl3/MeOH, form a thin film, then hydrate with buffered saline at a temperature above the material’s softening point; vortex and sonicate or extrude (100–200 nm membranes) to form SUVs.
Ethanol injection: inject an ethanolic lipid solution into stirred buffer; control final ethanol content (<10–20% v/v) and temperature to tune particle size.
Charge ratio: optimize N+/P− (for polyanion complexation) empirically across ~1:1 to 5:1 ranges depending on helper lipids and ionic strength.
Microemulsions for nanoparticle synthesis:
Oil phase: cyclohexane, isooctane, or toluene; co‑surfactants: short alcohols (1‑butanol) as needed.
Aqueous droplet size tuned by water‑to‑surfactant ratio (W0). Maintain inert atmosphere if metal precursors are air‑sensitive.
Ion‑pair extraction:
Combine aqueous anion source with organic solution of the surfactant; adjust pH to favor anionic form; mix vigorously, then allow phase separation. Back‑extract or wash to remove residual salts.
Analytical controls: measure hydrodynamic size (DLS), zeta potential, and residual solvent. Always confirm that the chosen solvent system is compatible with downstream assays and that no anionic components precipitate the surfactant.
Safety and Handling
Hazard classification details for this specific item are not provided in the Product Data.
GHS (Product Data):
Signal Word: Not specified for this item; refer to SDS.
H‑Statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
GHS Classification: Not specified for this item; refer to SDS.
General safety guidance for cationic quaternary ammonium surfactants (informative; defer to SDS):
Hazards: Often cause skin and eye irritation or burns; harmful if swallowed or inhaled as aerosols/dust; very toxic to aquatic life with long‑lasting effects. Avoid release to the environment.
PPE: Wear lab coat, chemical‑resistant gloves (e.g., nitrile), splash goggles; use a fume hood when handling powders/aerosols or preparing concentrated solutions.
Incompatibilities: Strong oxidizers; anionic surfactants and soaps (can precipitate as ion pairs); strong bases/acids may alter physical form; avoid reactive halide exchange with silver salts.
First aid (overview): Rinse skin/eyes with water for ≥15 min; remove contaminated clothing; if inhaled, move to fresh air; if ingested, rinse mouth—do NOT induce vomiting; seek medical attention in all cases.
Fire: Combustible organic solid; use CO2, dry chemical, or foam; quats may decompose to release irritating fumes (nitrogen oxides, HCl) on burning.
Handling tips: Minimize dust; warm gently to aid dissolution; prepare aqueous dispersions slowly with vigorous stirring to avoid clumping.
Always consult the product‑specific SDS for authoritative hazard and response information.
Solvent Selection
Dioleyldimonium chloride is a strongly amphiphilic, cationic lipid. Solvent choice is dictated by the need to either dissolve it molecularly (organic phase) or to disperse it into aggregates (aqueous phase).
Polarity class: amphiphile; highly hydrophobic tails with a permanent cationic head.
Moderate (often on warming): toluene, hexanes, cyclohexane, ethyl acetate.
Water: limited true solubility; forms micelles/vesicles above a formulation‑dependent CMC.
Practical choices:
Thin‑film hydration: dissolve in CHCl3/MeOH (2:1) or EtOH, evaporate to a film, then hydrate with buffer to form dispersions/liposomes.
Direct dissolution: make alcoholic stock (e.g., EtOH) for titration into aqueous media under high shear.
Analytical prep: CHCl3 or MeOH for HPTLC; isopropanol/water for some QC assays.
Comparison (general):
Versus shorter‑chain quats (e.g., CTAB), dioleyl species are less water‑soluble but form more stable bilayers/vesicles; better for membrane mimetics but less suitable for classical micellar catalysis in water.
Avoid anionic co‑surfactants/soaps (precipitation). If oxidative stability is critical, choose oxygen‑free solvents and minimize light exposure to protect the olefinic chains.
Storage and Reconstitution
Storage conditions (Product Data): Store at 2–8°C, protected from light, desiccated.
Shipped in (Product Data): Wet ice.
Practical guidance:
Light/oxygen protection: The oleyl chains contain double bonds susceptible to oxidation. Keep tightly closed under dry air or inert gas; minimize headspace and light exposure. Use amber vials when possible.
Moisture control: Hygroscopic uptake can alter handling and dispersion behavior. Store with a fresh desiccant. Warm sealed containers to room temperature before opening to avoid condensation.
Thaw/soften before use: If solid or highly viscous at 2–8°C, allow to equilibrate at room temperature or slightly above to ease weighing and dissolution. Do not overheat; avoid prolonged exposure to >50–60°C.
Stock solutions: Prepare concentrated stocks in ethanol, methanol, isopropanol, chloroform, or chloroform/methanol mixtures. For aqueous use, add the organic stock slowly to buffer under vigorous stirring to prevent local precipitation.
Freeze–thaw: Repeated freeze–thaw of aqueous dispersions can change particle size. Prepare single‑use aliquots of liposomal or micellar formulations and store at 2–8°C short‑term. Verify stability by DLS/zeta potential as needed.
For lot‑specific stability limits and retest dates, consult the CoA/Spec Sheet. Always follow your institution’s SDS and safety protocols during handling and disposal.
Structure and Identity
Dioleyldimonium chloride is a cationic, long‑chain quaternary ammonium surfactant typically bearing two unsaturated C18 (oleyl, C18:1 Δ9) hydrocarbon chains on a permanently charged nitrogen, paired with chloride as the counter‑anion.
Item-specific identifiers (from Product Data):
CAS: 7212-69-3
CID: 6436349
InChIKey: 354770 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general/literature description):
Core: Quaternary ammonium center (R2R′R″N+ Cl−) with two long, monounsaturated oleyl chains (–(CH2)7–CH=CH–(CH2)8–CH3) attached to nitrogen; remaining substituents are typically short alkyls or hydrogens depending on exact specification (not provided here).
2D description: A central N+ atom bound to four carbon substituents; two are extended aliphatic chains each containing one internal C=C bond, creating an amphiphilic, cylindrical molecule with a bulky hydrophobic domain and a compact cationic headgroup.
Notes: Exact atom connectivity, stereochemistry at the C=C (cis/trans), and substitution pattern should be confirmed from the Certificate of Analysis or detailed specification for this SKU.
Synthetic Utility
Although primarily a surfactant, dioleyl quaternary ammonium chloride can play several roles in synthesis and materials preparation (general/literature):
Soft templating/capping agent: Directs growth of inorganic nanoparticles (e.g., metal oxides, chalcogenides) in reverse micelles or microemulsions; tail length and unsaturation influence pore/particle morphology.
Phase‑transfer/extraction: The lipophilic cation pairs with inorganic/organic anions to facilitate extraction into nonpolar solvents—useful for purifying polyanionic dyes, acids, or for anion metathesis steps.
Surfactant‑assisted catalysis: Enhances interfacial area in biphasic reactions; cationic nature can concentrate anionic nucleophiles at the organic/water interface.
Film formation: Spin‑ or dip‑coating from alcoholic/chloroformic solutions yields cationic films that can be further modified via layer‑by‑layer assembly with polyanions (e.g., PSS) to build multilayer architectures.
Ion‑pair chromatography modifier: At low ppm–low mM levels, can act as a mobile‑phase additive for ion‑pairing of anionic analytes; compatibility with detectors and columns must be verified.
Tips:
Keep oxygen/light exposure low to protect olefinic chains during long syntheses.
Remove residual surfactant by solvent exchange, dialysis, or ion‑exchange resins when it is not part of the final product.
Verify chloride content if counter‑ion impacts downstream steps; metathesis to alternative anions (e.g., PF6−, BF4−) can be performed if needed.
Target Specificity
Not applicable. This product is a small‑molecule surfactant, not an antibody or affinity reagent. No target, epitope, or species reactivity information is relevant to this SKU.
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