11,14-Eicosadienyl methane sulfonate , CAS No.72996-07-7

CAS: 72996-07-7 Cat. No.: E1439919 分子式: C₂₁H₄₀O₃S 分子量: 372.61

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

概要

11,14-Eicosadienyl methane sulfonate (11,14-Eicosadien-1-ol,methanesulfonate) is an ester product.

Specifications

保管条件

Store at -20°C

入荷

Ice chest + Ice pads

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名前と識別子

分子量

372.61

Application Protocols

Not applicable. No immunoassay or bioassay protocols (e.g., WB, IHC, IF, FC) are defined for this small-molecule reagent. For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for general procedure guidance.

Biological Roles

This product is a synthetic small-molecule electrophile and is provided strictly for research use; it is not a known endogenous metabolite in this mesylate form.

• Context (general biochemistry):

  • C20:2 (eicosadienyl) chains occur in lipids and can influence membrane fluidity, packing, and phase behavior; however, the methanesulfonate ester is a synthetic activation used to install such chains onto other molecules.
  • Researchers may employ this reagent to generate lipidated probes, membrane anchors, or amphiphiles that mimic long-chain unsaturated lipid behavior in model membranes, nanoparticles, or protein conjugates.

• No biological activity or pharmacology is claimed or implied for this reagent. Any evaluation of biochemical interactions (e.g., membrane partitioning or protein binding) pertains to downstream products synthesized from this intermediate and must be determined empirically.

• Handling note for bio-oriented work:

  • Preserve alkene geometry during synthesis if mimicking natural lipid isomers is important for membrane studies. Verify E/Z content by NMR/LC–MS prior to biophysical assays.

Buffer Applications

This compound is a hydrophobic organic electrophile and is not a buffering agent. It does not form defined acid/base pairs suitable for pH control.

• For aqueous or biological experiments, it is typically incorporated into organic phases, liposomes, micelles, or organic co-solvent systems rather than dissolved in standard buffers.
• Select buffer systems appropriate to the bioassay for downstream analytes; any interaction with this reagent would be indirect via hydrophobic assembly.

Green Alternatives

• Greener solvent choices (literature/practice):

  • Replace DMF/DMSO where feasible with 2-MeTHF, CPME, propylene carbonate (PC), or acetonitrile (low-tox, recyclable) for many SN2 reactions. Use phase-transfer catalysis (e.g., TBAB, Aliquat 336) in toluene/2-MeTHF to enable inorganic nucleophiles at lower temperatures.
  • Employ ethanol/aqueous biphasic systems with PTC for iodide exchange or thiolations when substrate solubility permits.

• Process considerations:

  • Conduct reactions at the highest practical concentration to reduce solvent use; long-chain products typically permit higher solids due to low polarity.
  • Avoid chlorinated solvents when possible; if DCM is necessary for solubility/workup, use minimal volumes and ensure proper capture and recycling.

• Alternative leaving groups and activations (tradeoffs):

  • Tosylates (Ts) are less volatile and sometimes easier to crystallize/purify but slightly less reactive than mesylates; either can be acceptable based on stability/handling preferences.
  • Carbonate or carbamate activation (e.g., p-nitrophenyl carbonate) can avoid sulfonyl chlorides in upstream synthesis but may be less reactive in SN2 at C1.

• Comparison snapshot (general):

  • Mesylate in 2-MeTHF/PC: good rate, greener solvent profile, easier phase separation.
  • Mesylate in DMF/DMSO: fastest rates, difficult solvent removal, higher EHS burden.

Select conditions that deliver the target transformation with minimal solvent hazard, controlled temperature (to limit E2), and robust recyclability.

Pharmaceutical Uses

For research and process development only; not for human or veterinary use.

• Typical roles in pharma R&D and manufacturing (general):

  • Lipidation handle: Installation of a C20:2 chain onto APIs, peptides, oligonucleotides, dyes, or excipient backbones to tune permeability, depot behavior, and formulation performance (e.g., LNP components, micelles). Any performance gains must be determined experimentally.
  • Intermediate for excipient synthesis: Precursor to unsaturated long-chain amines, thiols, or alcohol derivatives that can serve as surfactants, emulsifiers, or components of self-assembled systems.
  • Pro-moiety precursor: Conversion to iodides/azides/amines enables rapid diversification to prodrug linkers in discovery workflows (no therapeutic claims).

• Regulatory status: No pharmacopeial monograph known for this specific substance (general note). If intended for GMP-related development, qualify via full analytical suite (ID, purity, residual solvents, alkene geometry, stability) and refer to CoA/Spec Sheet for item-specific data.

Physical Properties

Item-specific physicochemical specifications have not been provided for this catalog entry. The following notes are general/literature-based to guide handling of long-chain primary mesylates and should not be construed as product specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Long-chain mesylates of C≥18 are often low-melting solids or viscous oils; literature/general observation.)
• Boiling point / decomposition: Not specified for this item; refer to CoA/Spec Sheet. (Alkyl mesylates commonly decompose before or during distillation under atmospheric pressure; literature.)
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (qualitative, literature):
  • Good solubility in nonpolar and moderately polar organic solvents (e.g., hexanes, toluene, dichloromethane, THF, ethyl acetate).
  • Limited solubility in highly polar protic media (water, alcohols) due to the long hydrophobic chain, despite the polar mesylate headgroup.
• LogP: Expected to be high due to C20 hydrocarbon chain (literature expectation for long-chain alkyl sulfonate esters); not specified for this item.
• pKa: Not applicable (neutral sulfonate ester; no ionizable center in typical ranges).

Always consult the product’s CoA/SDS for definitive properties before process design.

Quality and Grades

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting typical grades (general guidance):
  • Research/biochemistry grade emphasizes low residual acidic/ionic impurities that can catalyze side reactions (e.g., elimination) or isomerize alkenes.
  • “Purified” or “95%+” grades for aliphatic mesylates generally control residual alcohol, sulfonyl chloride, and inorganic salts; these affect SN2 efficiency and downstream transformations.
  • HPLC grade solvents are recommended when performing sensitive substitutions or assembling lipid-like targets to minimize adventitious water and unknown UV-active contaminants.
• Stabilizers/antioxidants:
  • Not specified for this item. Mesylates are commonly supplied without stabilizers. If present, stabilizers would be listed on the CoA and may impact certain nucleophilic substitutions; remove by pre-washing or chromatography if necessary.
• Quality considerations specific to long-chain unsaturated mesylates (general best practices):
  • Control of alkene geometry (E/Z at Δ11 and Δ14) can be critical for downstream biological-mimetic assemblies. Verify by 1H/13C NMR and GC–MS/HRMS as needed.
  • Monitor hydrolysis (regeneration of alcohol) and elimination (formation of terminal/internal alkenes) during storage by TLC/GC.
  • Water content and residual acid promote side reactions; use Karl Fischer and acid number where applicable (not specified for this item).

Reaction and Applications

As a primary alkyl methanesulfonate, 11,14-eicosadienyl mesylate is a versatile electrophile for constructing long-chain unsaturated motifs in complex molecules and materials.

• Representative transformations (literature/general):
  • SN2 substitutions at C1 to install diverse functionalities while preserving Δ11,Δ14 alkenes:
    • Azidation (NaN3) → subsequent reduction to primary amine; entry to cationic lipids, lipidated linkers, and PEG–lipid conjugates.
    • Thiolation (RS−) → thioethers; anchors for gold/surface attachment or further oxidation to sulfoxides/sulfones.
    • Cyanation (CN−) → nitriles → amides/acids; handle with care.
    • Halide exchange (I−) → iodide for even faster alkylations.
    • Phosphonation (HP(O)(OR)2, via Michaelis–Arbuzov on iodide) → phosphonate lipids.
  • O-/N-alkylation of alcoholates/phenolates and amines to introduce a C20:2 chain onto scaffolds (glycerol, carbohydrates, peptides, dyes) to modulate membrane affinity and self-assembly.
  • Polymer/materials chemistry: End-capping or grafting onto nucleophilic polymers to create hydrophobe–hydrophile block materials and vesicle-forming amphiphiles.
• Practical tips:
  • Keep conditions strictly anhydrous to avoid hydrolysis back to the alcohol.
  • Use polar aprotic solvents for rate acceleration; add a solubilizing co-solvent for greasy substrates.
  • Primary mesylates favor SN2 over E2; elimination can occur under strong base/high temperature—monitor by TLC/GC for terminal alkene formation.
  • Protect the diene from radical initiators, peroxides, and prolonged heat if alkene geometry is critical.
• Downstream versatility:
  • The introduced C20:2 motif can be leveraged for lipid-mimetic behavior, micelle/vesicle formation, and improved partitioning into membranes or hydrophobic phases (general observation).

Reaction Conditions

General literature guidance for primary alkyl mesylates; optimize for your substrate and nucleophile. Values below are typical ranges and not item-specific specifications.

• Azidation to 11,14-eicosadienyl azide:

  • Reagents: NaN3 (1.2–3.0 equiv), polar aprotic solvent (DMF, DMSO, MeCN, or 2-MeTHF with PTC).
  • Conditions: 25–80°C, 2–24 h depending on solvent and loading. Monitor to avoid elimination.
  • Workup: Aqueous quench, extract into nonpolar solvent; carefully handle azide products.

• Thiolation to thioethers:

  • Reagents: RSH (1.2–2.0 equiv), base (K2CO3/NaH), solvent (acetone, MeCN, 2-MeTHF), 20–60°C.
  • Notes: Airtight conditions to limit oxidation; add catalytic KI to accelerate.

• Iodide formation (Finkelstein-like):

  • Reagents: NaI or TBAI (1.5–3.0 equiv), acetone, MeCN, or 2-MeTHF; 20–60°C.
  • Advantage: Generates a more reactive iodide for subsequent couplings.

• Amine alkylation (for tertiary amines/ammonium salts):

  • Reagents: Secondary amine (1.1–1.5 equiv), base (Et3N/K2CO3), solvent (MeCN, toluene with PTC), 20–50°C.
  • Control dilution to suppress bis-alkylation when monoalkylation is desired.

• Protecting alkene integrity:

  • Avoid strong mineral acids and extended heating. Use radical inhibitors if peroxide contamination is a concern.

• Typical monitoring:

  • TLC often poorly responsive for greasy chains; use GC (if volatile), LC–MS, or 1H NMR. Watch for elimination by emergence of vinyl proton signals at the chain terminus.

All conditions should be verified experimentally on small scale; consult primary literature and the SDS before scale-up.

Safety and Handling

• GHS/CLP classification, signal word, pictograms, and H-statements: Not specified for this item; refer to the SDS for authoritative information.
• General hazard profile (class- and functionality-based, literature):
  • Alkyl methanesulfonates are electrophiles and can act as alkylating agents; they may cause skin/eye irritation and are harmful if inhaled or ingested. Avoid contact and inhalation.
  • Long-chain hydrophobes can form persistent films; spills may be slippery.
• PPE and controls:
  • Wear lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (e.g., nitrile). Work in a functioning chemical fume hood.
• Incompatibilities and reactivity:
  • Hydrolyzes slowly with moisture; avoid water and strong nucleophiles during storage.
  • Bases and strong nucleophiles induce substitution or elimination; avoid unintended contact.
  • Avoid strong oxidizers and strong reducing agents. Protect unsaturated bonds (C=C) from radical initiators if alkene integrity is required.
• First aid (overview; defer to SDS):
  • Skin: Remove contaminated clothing, wash with soap and water.
  • Eyes: Rinse with water for ≥15 min; seek medical attention.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety:
  • Likely combustible organic; use CO2, dry chemical, or foam. Cool containers with water spray from a safe distance.
• Storage (item-specific): Store at −20°C. Keep tightly closed in a dry, inert atmosphere; protect from light and moisture. Shipments: Ice chest + ice pads (as provided).

Solvent Selection

This substrate is a hydrophobic, primary alkyl mesylate with internal C=C bonds. Solvent choice should balance substrate solubility with SN2 kinetics and alkene preservation.

• Polarity class and miscibility (general/literature):
  • Highly soluble in nonpolar and moderately polar aprotic solvents (hexanes, toluene, DCM, EtOAc, THF, MTBE, CPME). Limited solubility in water/alcohols.
  • For SN2, polar aprotics (DMF, DMSO, NMP, MeCN, PC) enhance nucleophilicity and rates but ensure substrate solubility; co-solvents (toluene/THF) may help.
• Typical choices by transformation:
  • Azidation/thiolation/cyanation: DMF, DMSO, MeCN, or 2-MeTHF/CPME with phase-transfer base; add 15–30% toluene if needed for solubility.
  • Halide exchange (I−): Acetone or 2-MeTHF with NaI (Finkelstein-like) to increase leaving group ability in situ.
  • O- or N-alkylation onto nucleophiles bearing poor solubility: Biphasic toluene–aqueous with PTC (e.g., TBAB) to retain alkene integrity at mild temperatures.
• Special considerations for unsaturated C20 chains:
  • Avoid strongly protic or acidic solvents that may isomerize alkenes.
  • Minimize high-temperature residence time in strongly polar media to reduce elimination.
• Quick comparison (general guidance):
  • DMSO/DMF: Fast SN2, good for salts; may be harder to remove from waxy products.
  • MeCN/2-MeTHF/CPME: Easier workup, moderate rates; often improved handling for greasy substrates.
  • Toluene/DCM: Excellent solubility; may require PTC or stronger nucleophiles.

Storage and Reconstitution

• Storage (item-specific): Store at −20°C. Shipments are provided in an ice chest with ice pads to maintain cold chain.
• Container and atmosphere:
  • Keep tightly sealed under inert gas (argon or nitrogen) in a dry environment. Use a desiccant in secondary containment to limit moisture ingress.
• Handling to preserve quality:
  • Allow container to warm to room temperature before opening to prevent condensation. Immediately re-cap after use. Minimize headspace and light exposure to protect unsaturated bonds.
  • Consider aliquoting into small vials to reduce repeated freeze–thaw and air exposure.
• Solution preparation (general):
  • Prepare stock solutions in dry, oxygen-free organic solvents (e.g., anhydrous DCM, THF, toluene, MeCN, or 2-MeTHF), typically 0.05–0.5 M depending on solubility and intended use. Use freshly dried bases/nucleophiles for SN2 reactions.
• Stability notes (general/literature):
  • Sensitive to hydrolysis (regenerates the alcohol) and base-promoted elimination; store cold and dry. Internal alkenes are susceptible to radical-induced isomerization/oxidation; avoid peroxides and prolonged heat.
• Disposal:
  • Treat as an organic electrophile/alkylating agent. Collect waste in halogen-free organic waste streams and dispose according to institutional and regulatory requirements.

Always consult the product’s SDS and CoA for definitive storage limits, stability data, and any item-specific precautions.

Structure and Identity

Research-use only aliphatic electrophile featuring a long ω-2, ω-5 diene chain terminated as a primary methanesulfonate (mesylate), suited for SN2 functionalization.

• Preferred name: 11,14-Eicosadienyl methane sulfonate (primary alkyl mesylate)
• CAS: 72996-07-7
• SKU: E1439919
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Structural features (interpretation of the name; general chemistry description):
  • A linear C20 aliphatic chain bearing two internal carbon–carbon double bonds at positions Δ11 and Δ14 (geometry typically defined during synthesis; not specified here).
  • A terminal primary alcohol has been converted to the methanesulfonate ester (–O–SO2–CH3), creating a good leaving group for nucleophilic substitutions.
  • Functional groups: alkenes (2×, internal), alkyl methanesulfonate (primary).
  • No heteroatoms in the chain aside from the terminal mesylate; no rings; no stereocenters in the parent skeleton (alkene geometries may impart E/Z isomerism).

Synthetic Utility

Key reactivity arises from the primary alkyl methanesulfonate (excellent leaving group) combined with a hydrophobic C20:2 scaffold that imparts lipid-like properties to products.

• Transformational map (literature/general):

  • SN2 to C–N: NaN3 → R–N3 → R–NH2 (Staudinger or catalytic hydrogenation). Useful for cationic lipids, amide coupling handles.
  • SN2 to C–S: RS− (thiolate) → thioethers; further oxidation or disulfide formation for responsive materials.
  • SN2 to C–X: I− (NaI/TBAI) → primary iodide enabling rapid subsequent couplings (e.g., Arbuzov to phosphonates; metal-catalyzed cross-couplings via in situ radical pathways under photoredox, literature dependent).
  • SN2 to C–O: RO− to install ethers; glycosylation-type O-alkylations onto unprotected sugars via PTC are feasible with care.
  • Chain-end elaboration to acids/esters via cyanation→hydrolysis or via iodide→lithium–halogen exchange then carbonation (advanced practitioners).

• Selectivity/compatibility:

  • Primary center biases SN2 over E2; moderate bases, lower temperatures, and polar aprotic solvents maximize substitution fidelity.
  • Internal alkenes tolerate many nucleophiles; avoid radical, acidic, or strongly basic conditions that provoke isomerization/polymerization.

• Purification and analysis:

  • Greasy substrates benefit from minimal silica exposure; use deactivated silica or reverse-phase methods. Monitor by 1H NMR (disappearance of OCH2–Ms signals; appearance of new CH2–X) and MS.

• Retrosynthetic value:

  • Serves as a convergent handle to append a defined C20:2 hydrophobe onto diverse nucleophiles late in synthesis, enabling modular SAR around the polar headgroup.

Target Specificity

Not applicable. This product is a small-molecule chemical intermediate and has no antigen/epitope, clone, or species reactivity. For biological studies, any “targeting” arises only after this reagent is converted to a specific conjugate or probe.

よくある質問

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 72996-07-7, the molecular formula is C21H40O3S, and the molecular weight is 372.61 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.