Cetalkonium Chloride-d , CAS No.1998128-85-0

CAS: 1998128-85-0 Cat. No.: C1444113 Formula: C₂₅H₃₉D₇ClN Peso molecolare: 403.14

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Cetalkonium Chloride-d 7 is the deuterium labeled Cetalkonium Chloride.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

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Nomi e identificatori

Peso molecolare

403.14

Application Protocols

No item-specific tested protocols are provided for this product; refer to CoA/Spec Sheet.

General research workflows where cetalkonium chloride analogues are used (for guidance only):

• Micellar reaction setup: Prepare a buffered aqueous solution (e.g., 50 mM phosphate, pH 7.4) containing surfactant at 5× CMC; add substrates (neat or dissolved in minimal co-solvent) and stir vigorously at the desired temperature. Monitor by TLC/GC/LC.
• Biphasic PTC reaction: Combine organic substrate solution (e.g., toluene) and aqueous base (e.g., 50% w/w NaOH). Add 1–5 mol% quaternary ammonium salt; stir vigorously. Upon completion, separate layers, quench, and purify.
• LC–MS internal standard use (deuterated form): Spike a known amount of Cetalkonium Chloride-d into samples and calibration standards; extract/analyze under identical conditions to the analyte quaternary ammonium. Monitor specific MRM transitions reflecting deuterium incorporation; correct for matrix effects via isotope-dilution quantification.

These are illustrative, literature-style procedures; optimize concentrations, temperatures, and solvent ratios for your system. Always consult the SDS and perform small-scale pilots before scaling.

Biological Roles

General/literature context for quaternary ammonium surfactants (applies to the non-deuterated parent):

• Mode of action: Cationic surfactants interact strongly with negatively charged biomembranes and biopolymers (e.g., phospholipid headgroups, proteins, nucleic acids). The long alkyl chain partitions into lipid bilayers while the quaternary ammonium head disrupts packing, leading to increased permeability and potential membrane disruption.
• Binding/complexation: Ion pairing with anionic biomolecules (e.g., DNA, polysaccharides) can lead to precipitation or compaction; used in some research protocols for cell lysis, membrane solubilization, and phase separation.
• Deuterated analogue utility: Isotopic labeling enables tracing of adsorption, transport, and biodegradation pathways using LC–MS, providing insight into environmental fate or interaction with biological matrices.
• Enzymatic interactions: Quaternary ammonium compounds can denature or inhibit enzymes at sufficient concentrations by altering protein conformation and microenvironment; effects are concentration- and matrix-dependent.

Important limitations:

• Strong, non-specific interactions are typical; there is no inherent target selectivity for specific biomolecules without additional design.
• Cytotoxicity and irritation potential are common for cationic surfactants; handle with care and follow institutional safety policies.

Note: This section describes general biochemical behavior; no medical or clinical claims are implied. For experimental planning, determine concentration ranges that achieve desired permeabilization or solubilization while minimizing nonspecific damage.

Buffer Applications

This product is not a buffer reagent and is not typically used to establish or maintain pH.

Practical lab notes (general/literature for cationic surfactants):

• Can be incorporated into buffered solutions (e.g., phosphate, Tris, HEPES) as an additive for membrane permeabilization, micellar solubilization, or control of surface interactions. Surfactant addition may alter buffer ionic strength and apparent pH; verify with a calibrated pH meter after addition.
• Avoid combining with anionic buffer components or detergents (e.g., citrate at high concentrations, SDS) that can form inactive ion pairs or precipitates. If compatibility is uncertain, perform small-scale tests.
• Typical working concentrations for surfactant effects range from below CMC (to modify interfacial tension) to several times CMC (to form stable micelles). Optimize empirically based on assay readout.

For preparing true buffer systems (pH control), refer to dedicated buffering agents (Good’s buffers, phosphate, acetate, carbonate, etc.).

Green Alternatives

Perspective: Quaternary ammonium chlorides are effective but can be persistent and exhibit aquatic toxicity. Where feasible, consider greener surfactant systems or conditions that reduce environmental impact.

Comparison (general/literature):

• Cetalkonium Chloride (CKC) vs. alternatives
  • Esterquats (biodegradable cationic surfactants):
    • Pros: enhanced biodegradability due to cleavable ester linkages; reduced environmental persistence.
    • Cons: lower thermal/alkaline stability; different CMC and interfacial behavior; may not match CKC’s micellar catalysis profile.
  • Zwitterionic surfactants (e.g., betaines):
    • Pros: milder toxicity, good compatibility with anionics/nonionics; effective over wide pH; lower ecotoxicity.
    • Cons: Lack permanent cationic charge—different adsorption to negatively charged surfaces; reduced PTC efficacy.
  • Nonionic sugar-based surfactants (alkyl polyglucosides):
    • Pros: renewable feedstocks; good biodegradability; low toxicity; effective wetting.
    • Cons: Limited use in PTC; different micellar structures and CMC.
  • Micellar catalysis with TPGS-750-M (aqueous nanomicelles):
    • Pros: enables organic reactions in water with reduced organic solvent; established green metrics improvements.
    • Cons: Different mechanism vs. cationic quats; not suitable for anion-transfer PTC.

Greener practice tips:

• Use water-rich solvent systems to minimize VOCs.
• Optimize surfactant loading to minimum effective CMC multiples.
• Implement closed-loop aqueous streams and activated carbon or ion-exchange treatment for surfactant-containing waste.
• Consider solid-supported quats for easier recovery/reuse when PTC behavior is essential.

Pharmaceutical Uses

No therapeutic or clinical claims are made; for research use only.

General/literature context for the non-deuterated parent (cetalkonium chloride) as an excipient:

• Role: cationic surfactant/preservative and penetration/permeation enhancer in some research formulations. The benzylated quaternary ammonium structure confers antimicrobial preservation and strong surface activity.
• Formulation impacts: can increase wettability, emulsification, and adsorption to negatively charged surfaces (e.g., ocular/mucosal tissues in formulation research). May interact with anionic actives or polymers—compatibility testing is essential.
• Analytical and development uses: deuterated analogue can serve as an internal standard for quantifying residual quaternary ammonium surfactants in process streams or dosage-form extracts via LC–MS/MS.
• Regulatory status: Specific pharmacopeial monographs often exist for related quats (e.g., benzalkonium chloride mixtures); cetalkonium chloride may be referenced in formulation literature. For this deuterated research material, no pharmacopeial status is implied.

Cautions:

• Potential for irritation; concentration limits and risk assessments are required in any formulation research.
• Avoid anionic excipients that form insoluble ion pairs; verify preservative efficacy and stability empirically.

Always consult relevant regulations and perform appropriate non-clinical testing if using in pre-formulation studies.

Physical Properties

Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.

General/literature properties for the non-deuterated parent (cetalkonium chloride; values are typical ranges and for reference only):

• Physical state: waxy solid or powder; strongly hygroscopic; cationic surfactant.
• Solubility: highly soluble in water and lower alcohols; soluble in polar organics (e.g., methanol, ethanol, isopropanol); limited solubility in nonpolar hydrocarbons; enhanced solubility in mixed aqueous/organic systems due to micelle formation.
• Critical micelle concentration (CMC, literature): typically low micromolar to sub-millimolar in water for C16 benzyl quats; actual value depends on counterion, ionic strength, and temperature.
• LogP/logD (qualitative): exhibits amphiphilicity; the cationic head imparts high aqueous affinity while the C16 tail drives association with hydrophobic phases; effective partitioning into membranes and organic phases in presence of ion-pairing.
• Thermal behavior: lacks a sharp boiling point (decomposes before boiling at atmospheric pressure); softening/melting can occur over a range depending on hydration and counterion; drying reduces softening range.
• Refractive index and UV cutoff: Not commonly defined for solids; aromatic chromophore (benzyl) exhibits UV absorbance around 200–260 nm (literature qualitative note).

Deuteration note: Isotopic substitution (H→D) minimally affects bulk physical properties but changes exact mass and can subtly shift spectroscopic signatures (NMR, MS, IR—C–D stretches near ~2100–2200 cm−1, literature). Always verify with CoA for this deuterated lot.

Quality and Grades

• Grade/purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Identity controls for deuterated materials (general guidance):
  • Verification by high-resolution MS to confirm isotopic mass shift relative to non-deuterated cetalkonium chloride.
  • 1H/2H NMR to document labeling efficiency and site(s) of deuteration; IR to observe C–D stretches.
  • Chloride content and counterion identity confirmed by ion chromatography or argentometric titration.
• Typical impurities (literature): residual non-deuterated analogue, alternate chain length benzyl quats, residual solvents, water. For cationic surfactants, water content and halide balance influence performance.
• What grade implies (context): If designated as research-grade, the item is suitable for analytical and synthetic laboratory use, not for therapeutic or diagnostic applications. HPLC-grade or LC–MS-grade labels (if present on CoA) would indicate low UV background and minimal nonvolatile residue—particularly important for trace analysis using surfactant-mediated extraction or LC–MS sample prep.
• Stabilizers: None are typically added to quaternary ammonium chlorides; if a stabilizer or anti-caking agent is used, it will appear on the CoA. Not specified for this item; refer to CoA/Spec Sheet.

Note: For isotopically labeled quats, report “%D incorporation” and distribution (site-specific vs. overall) on the CoA to ensure experimental reproducibility across kinetic isotope effect or tracer studies.

Reaction and Applications

Research-only applications (general/literature for cetalkonium chloride; extendable to the deuterated analogue):

• Phase-Transfer Catalysis (PTC):
  • Functions as a lipophilic cation to shuttle anions (e.g., CN−, OH−, halides) from aqueous to organic phases, enabling nucleophilic substitutions, condensations, and oxidations under biphasic conditions.
  • Practical tips: maintain vigorous stirring to maximize interfacial area; control aqueous base strength; choose organic solvents with adequate polarity (toluene, dichloromethane, MTBE) and monitor for emulsions.
• Micellar/Colloidal Catalysis and Media Effects:
  • Forms micelles in water that can concentrate hydrophobic reagents, accelerating reactions such as SN1/SN2, cyclizations, and some organometallic transformations under aqueous or mixed-solvent conditions.
  • Aromatic benzyl substituent can participate in ion pairing and π–π interactions, potentially altering substrate partitioning vs. non-benzyl quats.
• Materials and Interfaces:
  • Useful in preparing cationic emulsions, dispersions, and surface modifications; facilitates adsorption on negatively charged substrates (silica, clays, some polymers) to modulate wettability and adhesion.
• Analytical/Isotopic Uses (deuterated form):
  • Internal standard or tracer in mass spectrometry-based quantification of related quaternary ammonium surfactants.
  • Probe for kinetic isotope effects in degradation, adsorption, or transport studies.

Caveats:

• Anionic contaminants (soaps, SDS) can neutralize activity by forming insoluble ion pairs.
• Elevated salt can raise the Krafft point and alter micelle size; temperature control is important.
• Avoid strong oxidants; quaternary ammonium salts can undergo N-dealkylation under harsh conditions.

Reaction Conditions

Guidance below is general/literature for benzylated quaternary ammonium chlorides and should be adapted experimentally. It is not item-specific.

• Phase-transfer catalysis (biphasic SN2, alkylations):
  • Typical catalyst loading: 1–10 mol% quaternary ammonium salt relative to limiting reagent.
  • Aqueous phase: 10–50% w/w NaOH or KOH for strong base-mediated reactions; milder bases (carbonate, bicarbonate) for sensitive substrates.
  • Organic phase: toluene, chlorobenzene, DCM, MTBE, or cyclohexane/ether blends; choice balances substrate solubility and safety.
  • Temperature: 0–80°C depending on substrate stability; elevated temperatures increase mass transfer and rate.
  • Agitation: vigorous stirring (≥600 rpm in lab reactors) or overhead stirring to minimize mass-transfer limitation.
  • Time/yield: many substitutions reach >70% conversion within 1–6 h; optimize empirically (literature ranges).
• Micellar catalysis in water:
  • Surfactant concentration: 2–10× CMC to ensure stable micelles; buffer ionic strength tunes micelle size and Krafft point.
  • Co-solvent: 5–20% EtOH, i-PrOH, or acetonitrile can assist substrate solubilization while retaining aqueous character.
  • Temperature: ambient to 60°C as needed to remain above Krafft temperature and maintain micellization.
• Workup tips:
  • Break emulsions with salt addition (brine), gentle heating, or centrifugation.
  • Remove residual quat by extraction into aqueous acidic washes or adsorption on silica/clays; strong binding to glassware may require surfactant-containing rinses.

Note: Deuteration does not materially change catalytic behavior; it is mainly beneficial for analytical tracing. Always validate conditions on small scale.

Safety and Handling

Item-specific GHS and hazard statements: Not specified for this item; refer to SDS for SKU C1444113.

General safety profile (literature/analogous quaternary ammonium chlorides):

• Likely hazards: corrosive/irritant to skin and eyes; harmful if swallowed; very toxic to aquatic life with long lasting effects (many benzyl C16 quats carry GHS Skin Corr./Irrit. and Aquatic Acute/Chronic classifications). Do not rely on this summary for compliance—consult the SDS for definitive classification.
• PPE: use lab coat, chemical-resistant gloves (e.g., nitrile), splash goggles or face shield. Handle solids to avoid dust/aerosol formation; use a fume hood.
• First aid (general):
  • Skin/eye contact: immediate decontamination with copious water for ≥15 minutes; remove contaminated clothing; seek medical attention per SDS guidance.
  • Ingestion/inhalation: move to fresh air; rinse mouth; do not induce vomiting; obtain medical attention.
• Incompatibilities: strong oxidizers; anionic surfactants and soaps (can form inactive ion pairs/precipitates); strong bases/acids may influence stability/phase behavior. Avoid mixing with bleach or hypochlorites.
• Special risks: hygroscopic; may generate slippery surfaces when spilled; cationic surfactants can cause persistent foaming. Prevent environmental release; collect with inert absorbent.
• Fire safety: product is organic and combustible; use water fog, CO2, dry chemical, or foam; quaternary salts may decompose to release irritating fumes (e.g., HCl, nitrogen-containing species). Thermal decomposition can be corrosive and noxious.

Always defer to the product-specific SDS for authoritative safety, exposure limits, and spill/incident response.

Solvent Selection

Applicability: Cetalkonium Chloride-d is a cationic surfactant; solvent choice governs micellization, solubilization of hydrophobes, and interfacial activity.

• Polarity/miscibility (general/literature for cetalkonium chloride):
  • Readily soluble in water and lower alcohols (MeOH, EtOH, i-PrOH). Forms clear aqueous solutions that can foam; CMC in the low µM–mM range depending on ionic strength and temperature.
  • Soluble in polar aprotic solvents (e.g., acetonitrile) to a limited extent; improved by small water content.
  • Poorly soluble in nonpolar solvents (hexanes, toluene) unless paired with co-solvents or as ion pairs with lipophilic counterions.
• Selection guidance:
  • For micellar catalysis or solubilization of hydrophobic substrates, use buffered water/EtOH or water/MeOH mixtures; adjust ionic strength to tune CMC and aggregate size.
  • For phase-transfer catalysis in biphasic organic/aqueous systems, select an organic phase with adequate polarity (e.g., toluene, chlorinated solvents, or ethers) and an aqueous alkaline phase; surfactant transports anions across the interface.
  • For analytical sample preparation, water with 1–20% alcohol can reduce viscosity and improve wetting.
• Comparison (literature):
  • Cetyltrimethylammonium bromide (CTAB) vs. cetalkonium chloride (CKC): CKC’s benzyl substituent can increase hydrotropic ability and UV absorbance; CTAB often gives higher Krafft points but lower UV background.
  • Chloride vs. bromide counterions: bromides are more common in micellar catalysis; chlorides can be preferable in chloride-sensitive analyses.

Note: Deuteration does not significantly alter solvent compatibility; choose based on application and counterion effects.

Storage and Reconstitution

• Storage conditions (item-specific): Store at -20°C.
• Shipping (item-specific): Shipped in an ice chest with ice pads to maintain a cold chain.
• Long-term handling (general good practice for quaternary ammonium salts):
  • Keep tightly closed in the original container to minimize moisture uptake; product may be hygroscopic and can cake upon exposure to humidity.
  • Allow container to equilibrate to room temperature before opening to avoid condensation.
• Reconstitution/dissolution (general guidance; item-specific solubility not provided):
  • Readily dissolves in water and lower alcohols (MeOH, EtOH, i-PrOH) with gentle stirring; warm mildly (25–40°C) if needed. For anhydrous organic solutions, use dry alcohols or polar aprotics and protect from moisture.
  • Prepare concentrated stock solutions as appropriate for your application (e.g., 10–100 mg/mL), then dilute into working media. Filter sterilize through compatible membranes if required for microbiologically controlled studies.
• Stability considerations (general):
  • Avoid strong oxidizers and extremes of pH during storage. Prolonged exposure to light and heat can accelerate degradation.
  • For deuterated materials, minimize repeated open–close cycles to reduce isotopic exchange at labile positions (if present).
• Specified values: Any item-specific concentration limits, water content, or assay/purity specifications are Not specified for this item; refer to CoA/Spec Sheet.

Always consult the CoA/SDS for lot-specific guidance and stability data before use.

Structure and Identity

Overview: Cetalkonium Chloride-d is the deuterium-labeled analogue of cetalkonium chloride, a long-chain, benzylated quaternary ammonium chloride used as a cationic surfactant and phase-transfer reagent in research settings.

• Molecular formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• SMILES (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Structural features (general/literature, describing the non-deuterated parent):
  • Quaternary ammonium center bearing three organic substituents and a chloride counterion.
  • Typical substituent pattern for cetalkonium: one benzyl group, two methyl groups, and one hexadecyl (C16) alkyl chain on nitrogen, giving a permanently charged cation paired with Cl−.
  • Deuterium labeling (this product): positions and degree of deuteration are not specified; labeling typically resides on selected aliphatic or benzylic hydrogens to facilitate mass spectrometric tracing and NMR discrimination.
• 2D structure description (general/literature): A tetraalkyl(benzyl)ammonium cation with a long linear C16 chain extending from the nitrogen, two short methyl substituents, and a benzyl substituent (phenyl–CH2–) attached to the quaternary nitrogen; associated with a chloride anion. The permanent cationic center confers strong ionic character and surfactant behavior.

Note: Exact isotopic labeling pattern governs the precise formula and exact mass for Cetalkonium Chloride-d; consult the CoA for definitive identity parameters specific to SKU C1444113.

Synthetic Utility

As a benzylated quaternary ammonium chloride, Cetalkonium Chloride-d (deuterated) provides value in synthesis both functionally and analytically.

• Phase-transfer catalyst (PTC):
  • Promotes nucleophilic substitutions, condensations, and alkylations by transferring anions (e.g., CN−, HS−, OH−) into organic solvents. Particularly effective under biphasic conditions with strong aqueous base.
  • Benzyl substituent can facilitate ion pairing and sometimes enable benzylic activation pathways under specific conditions.
• Micellar media promoter:
  • Enables reactions in water or water-rich media by sequestering hydrophobic substrates within micelles, often improving rates and selectivity; can reduce need for volatile organic solvents.
• Isotopically labeled tracer:
  • The deuterated form is a convenient internal standard for LC–MS quantification of cetalkonium or related quats in process monitoring, extraction, or environmental fate studies.
• Retrosynthetic role:
  • Quaternization protocols (e.g., alkylation of tertiary benzyl dimethylamine with a C16 alkyl halide) illustrate modular access to tailored headgroup/chain lengths; knowledge of this synthesis aids customization of surfactant libraries for structure–property studies.

Considerations:

• Counterion effects: chloride vs. bromide can influence solubility and PTC activity; chloride is less nucleophilic and may be preferred in halide-sensitive transformations.
• Compatibility: avoid anionic reagents/detergents that neutralize functionality. Control water content to manage Krafft temperature and viscosity for reproducibility.

Target Specificity

Not applicable. This product is a small-molecule cationic surfactant, not an antibody or affinity reagent. There are no antigen/epitope targets, isotypes, or species reactivity parameters associated with this item.