HAPC-Chol , CAS No.1027801-73-5

CAS: 1027801-73-5 Cat. No.: H1440128 分子式: C₃₃H₅₈N₂O₃ 分子量: 530.83

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

概要

HAPC-Chol is a cationic cholesterol that can be used as a component of lipoplexes complexes.

仕様

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

530.83

Application Protocols

Item-specific validated protocols are not provided for this SKU.

General research workflows for sterol-conjugated small molecules (not item-specific):

• Stock solution preparation: Dissolve in dry DMSO or CHCl3 (or CHCl3:MeOH 9:1) to 1–10 mM. Warm gently (30–40°C) and sonicate if needed. Store small aliquots at −20°C to minimize freeze–thaw.
• Thin-film hydration (for liposomes/NPs): Co-dissolve with helper lipids in CHCl3 or CHCl3:MeOH, evaporate to a thin film, desiccate ≥1 h, hydrate with pre-warmed buffer (e.g., HEPES, pH 7.4), vortex, and optionally probe-sonicate or extrude through 100–200 nm membranes.
• Direct assay addition: If compatible, add DMSO stocks slowly to aqueous media under vigorous mixing to a final DMSO ≤1–2% v/v. Inspect for precipitation; filter (0.22 μm) if needed and compatible.
• Analytical confirmation: Verify incorporation or concentration by HPLC/LC–MS. For lipid assemblies, use phosphorus assay for total lipid (if applicable) and dynamic light scattering for size and PDI.

Note: Optimize concentrations and conditions empirically for your system, and consult the CoA/SDS for any item-specific constraints.

Biological Roles

Item-specific: No biological function is specified for this SKU. For research use only.

General/literature perspective on cholesterol-conjugated small molecules (not item-specific):

• Membrane affinity: Cholesterol’s sterol core partitions into lipid bilayers, increasing local concentration of the conjugated moiety at membrane interfaces.
• Trafficking: Cholesterol motifs can influence endocytic uptake and intracellular trafficking pathways in cell-based research, often localizing to lipid rafts and ordered domains.
• Biophysical effects: Inclusion of sterol-conjugated components can modulate bilayer order, phase separation, and permeability in model membranes, affecting probe or cargo presentation.
• Oligonucleotide/peptide tagging: Cholesterol conjugation is a common strategy in research to enhance membrane association of nucleic acids and peptides for mechanistic studies.

Caveats:

• Biological outcomes can be highly dependent on linker chemistry, headgroup charge, and density within the membrane. Always conduct appropriate controls (e.g., unconjugated probe, alternative lipid anchors) and titrate concentrations to minimize nonspecific perturbation of membranes.
• Do not infer therapeutic properties from these general roles; this product is supplied strictly for laboratory research use.

Buffer Applications

This item is a hydrophobic small molecule and is not typically used as a classical aqueous buffer component.

General guidance for working solutions (not item-specific):

• Prepare a concentrated stock in an appropriate organic solvent (e.g., DMSO, THF, CHCl3, or CHCl3:MeOH) depending on solubility and stability, then dilute into the experimental medium while maintaining final cosolvent content typically ≤1–2% v/v for cell-based assays.
• For liposome or nanoparticle preparations, avoid direct addition into aqueous buffers; instead, use thin-film hydration or solvent injection methods, followed by buffer exchange (e.g., HEPES, PBS) after assembly.
• If precipitation is observed upon dilution into buffer, reduce the addition rate, increase temperature slightly, or adjust the organic cosolvent fraction within acceptable limits for your system.

Green Alternatives

Item-specific: no specific solvent or process is mandated by the Product Data.

General sustainability considerations for sterol-containing conjugates (not item-specific):

• Solvent selection: Prefer ethyl acetate, isopropanol, or 2-methyltetrahydrofuran (2-MeTHF) when compatible with solubility and stability. Replace CHCl3/CH2Cl2 with greener halogen-free options where practical.
• Workflows: Use miniaturized formulation screens (microplate-based) to reduce solvent volumes. Employ rotary evaporation with efficient condensers and recover solvents for reuse when purity allows.
• Energy use: Many sterol conjugates dissolve faster with mild heat; however, optimize to the lowest effective temperature to minimize energy consumption and potential degradation.

Comparison of common choices (literature, general):

• CHCl3 vs 2-MeTHF: CHCl3 offers superior sterol solubility but is toxic and ozone-depleting; 2-MeTHF is bio-based and greener, though solubility can be lower and water content control is important.
• DCM vs EtOAc: DCM has excellent dissolving power but higher environmental impact; EtOAc is greener and often sufficient for workup/purification.
• DMSO vs Cyrene (dihydrolevoglucosenone): For some polar conjugates, Cyrene may substitute DMSO/DMF; validate stability and solubility.

Quality note:

• Any change in solvent or process should be validated analytically (HPLC, LC–MS, NMR) to ensure no degradation or polymorphic changes occur.

Pharmaceutical Uses

No pharmacopeial status or excipient designation is provided for this item.

General/literature context (not item-specific; research use only):

• Cholesterol-bearing conjugates are widely studied in formulation research as membrane anchors in liposomal systems, lipid nanoparticles, and surface-modified carriers. They can influence bilayer rigidity, stability, and biodistribution surrogates in model systems.
• In pre-formulation studies, sterol conjugates may be evaluated for their effects on encapsulation efficiency, release kinetics, and colloidal stability when combined with helper lipids.
• Manufacturing considerations (research scale): solubility in volatile organic solvents for thin-film methods; compatibility with ethanol injection or microfluidic mixing; filterability (0.22 μm) and avoidance of particulate formation.

Compliance note:

• This product is supplied for research use only. No claims are made or should be inferred regarding therapeutic use, safety, or efficacy in humans or animals.

Physical Properties

Item-specific (from provided Product Data):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Computed/literature values (general guidance; not specific to this item):

• Cholesterol conjugates are typically non-volatile solids or waxy solids with high hydrophobicity (logP often >5; literature, varies with headgroup/linker).
• Solubility (literature, typical): sparingly soluble in water; soluble in chlorinated solvents (CH2Cl2, CHCl3), THF, toluene; often soluble in polar aprotic solvents like DMSO/DMF depending on headgroup.
• Thermal behavior: many sterol conjugates show softening between 40–90°C (literature). Exact melting point depends strongly on the conjugated moiety and crystallinity.
• Spectral characteristics: UV absorption mainly from headgroup if aromatic; cholesterol core has weak UV chromophores (literature). FTIR and NMR are standard for identity confirmation.

Important note:

• Because no item-specific physical constants were supplied, do not rely on the above as specifications. For experimental planning, consult the product’s CoA/Spec Sheet and SDS, and perform a small-scale solubility screen in your intended solvent system.

Quality and Grades

Item-specific (from provided Product Data):

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret common grades (general guidance; not item-specific):

• Research grade: suitable for discovery and development workflows, screening libraries, and synthetic use. Purity is typically validated by HPLC/LC–MS or NMR, but acceptance criteria vary by supplier.
• HPLC grade solvents vs compound grade: For small molecules like HAPC‑Chol, the grade usually refers to chemical purity and identity rather than solvent UV cutoffs.
• Stabilizers/additives: Some sterol conjugates are shipped with desiccants or under inert gas to preserve linker integrity. Any stabilizer or residual solvent content should be listed on the CoA.

Practical advice:

• Request the latest CoA/Spec Sheet for this exact lot to confirm purity assay method (e.g., HPLC area %, qNMR), identity (HRMS, 1H/13C NMR), water content (KF), residual solvents, and if applicable, stereochemical confirmation.
• If using in biophysical assays or materials assembly, consider additional in‑house QC (DSC/TGA for thermal profile, MALDI/ESI‑MS for adducts, and thin‑film FTIR for linker integrity) depending on your application.

Reaction and Applications

Item-specific (from provided Product Data):

• Manufacturer application text was not provided. No specific reactions are claimed for this SKU.

General/literature context for cholesterol-tagged small molecules (not item-specific):

• Membrane anchoring: Cholesterol conjugation is widely used to localize small molecules, peptides, and probes to lipid membranes, enhancing cell association and residence time in model systems.
• Materials assembly: Incorporated into liposomes, lipid nanoparticles, and supported bilayers to tune fluidity, phase behavior, and cargo retention in research formulations.
• Probe design: Cholesterol tags can improve binding of molecular probes to membrane proteins by increasing local concentration at membranes.
• Delivery research: Used as a hydrophobic anchor in research on oligonucleotide, peptide, or small-molecule delivery to cells; often compared to other anchors (e.g., stearyl, tocopherol).

Practical tips (general):

• Combine with helper lipids (e.g., phosphatidylcholines, DOPE, cholesterol) and charged lipids to achieve desired zeta potential and phase behavior in model systems.
• Validate incorporation by analytical methods: TLC/HPTLC with phosphomolybdic or anisaldehyde stains; LC–MS of lipid extracts; 1H NMR in CDCl3/CD3OD mixtures.
• Control of loading: When co-formulating, start with 1–10 mol% of the conjugate relative to bulk lipids and titrate based on functional readouts.

Reaction Conditions

No item-specific reaction conditions are provided for this SKU.

General/literature conditions for assembling cholesterol conjugates (not item-specific):

• Carbonate formation and coupling: Cholesterol + chloroformate (e.g., p‑nitrophenyl or NHS carbonate) in CH2Cl2 with base (pyridine/Et3N/DIPEA) at 0–25°C, then couple to amines/alcohols of the partner moiety; typical times 1–16 h.
• Ester formation: Cholesteryl chloroformate or EDCI/DMAP-mediated coupling with carboxylic acids/alcohols in CH2Cl2 or THF at 0–25°C.
• Urethane/carbamate: Reaction of cholesteryl chloroformate with amines; monitor by TLC (anisaldehyde stain) or LC–MS.
• Click chemistry (CuAAC): Alkyne–azide coupling in tBuOH/H2O or DMF with CuSO4/ascorbate or CuI/ligand at RT; chelate copper or purify carefully to remove residual metal.
• Workup tips: Thoroughly wash organic layers with dilute acid/base and brine to remove catalysts and bases; dry over anhydrous Na2SO4 or MgSO4; avoid prolonged exposure to strong base that can induce elimination at the sterol C3 linkage.

Expected outcomes (literature):

• Yields vary widely (40–85%) depending on steric congestion and headgroup functionality. Purity often improves after trituration from cold MeOH or acetone to remove unreacted sterol or oligomers.

Safety and Handling

Item-specific (from provided Product Data):

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
• Storage conditions: Store at -20°C
• Shipping: Shipped in ice chest + ice pads

General laboratory safety (applicable good practice):

• Handle in a chemical fume hood while wearing appropriate PPE: lab coat, safety glasses, and chemically resistant gloves. Minimize dust and aerosol formation. Avoid inhalation, ingestion, and skin/eye contact.
• Incompatibilities (general for hydrophobic organics): strong oxidizers; avoid prolonged exposure to light/heat that may promote degradation of linkers (e.g., esters/carbonates/urethane). Use amber containers if the conjugate contains UV‑sensitive chromophores.
• Spill/first aid (general): absorb small spills with inert material (e.g., vermiculite), collect for disposal. In case of skin/eye contact, rinse with water for at least 15 minutes and seek medical evaluation. If inhaled, move to fresh air. If ingested, do not induce vomiting; seek medical attention.
• Waste: dispose of according to institutional and local regulations for organic chemical waste.

Always defer to the manufacturer SDS and the product’s CoA/Spec Sheet for authoritative hazard, toxicity, and handling instructions specific to this SKU.

Solvent Selection

Item-specific (from provided Product Data):

• No solvent recommendations or solubility data were provided. Refer to CoA/Spec Sheet and test on small scale.

General/literature guidance for cholesterol-containing conjugates (not item-specific):

• Polarity and miscibility: Typically highly lipophilic; soluble in CHCl3, CH2Cl2, THF, toluene; variable solubility in DMSO/DMF depending on headgroup and linker; minimal water solubility.
• Stock solutions: For biochemical screening, DMSO (anhydrous) is often used; gently warm/sonicate to aid dissolution. For thin-film lipid work, CHCl3 or CHCl3:MeOH mixtures are common to co-dissolve components before solvent evaporation and hydration.
• Film rehydration: If formulating into liposomes or micelles with other lipids, dissolve all components in a common volatile solvent, evaporate to a thin film, desiccate, then hydrate above the highest Tm of components; use vortexing and brief bath sonication.
• Avoid: Strongly protic conditions or basic aqueous media may hydrolyze ester/carbonate linkers if present; select solvents accordingly.

Comparison (typical choices):

• CHCl3: excellent sterol solubility; volatile; toxic—use in fume hood.
• CH2Cl2: similar to CHCl3; lower boiling.
• THF: good for sterols; miscible with alcohols; susceptible to peroxides—use inhibitor-aware fresh solvent.
• DMSO: convenient for bioassays; may require warming; high boiling—harder to remove.

Storage and Reconstitution

Item-specific (from provided Product Data):

• Storage conditions: Store at -20°C
• Shipped in: Ice chest + Ice pads

General handling guidance (not item-specific):

• Keep container tightly closed under inert atmosphere or desiccated conditions to protect from moisture and oxidation, especially if ester/carbonate linkers are present.
• For long-term storage, protect from light (amber vial) and minimize headspace. Avoid repeated freeze–thaw; partition into single-use aliquots upon first opening.
• Reconstitution: Prepare concentrated stocks in suitable dry solvents (e.g., DMSO, CHCl3, CH2Cl2, THF), based on small-scale solubility tests. If preparing for aqueous use, employ thin-film hydration or solvent-switch techniques rather than direct dissolution in water.
• Stability checks: Periodically assess integrity by HPLC/LC–MS or 1H NMR, especially after 6–12 months at −20°C or after temperature excursions.

Disclaimer:

• Where any parameter is not specified above, refer to the product’s CoA/Spec Sheet and SDS for definitive guidance. This product is supplied for research use only.

Structure and Identity

Overview: HAPC-Chol is listed as a small molecule/compound library member. The exact structural identifiers were not provided in the Product Data.

Item-specific (from provided Product Data):

• Chemical name: Not specified for this item; refer to CoA/Spec Sheet.
• CAS: 1027801-73-5
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

General/literature context (not item-specific):

• The name “HAPC‑Chol” suggests a cholesterol-containing conjugate (e.g., a small-molecule warhead or linker appended to a cholesterol motif) commonly used to enhance membrane association and lipophilicity. Confirm actual structure on the CoA.
• If it is a cholesterol conjugate, typical structural features include: a sterol tetracyclic core (cholestane), one or more linkers (e.g., carbonate/ester/urethane/amide or triazole), and a terminal functional headgroup (the “HAPC” portion). Stereochemistry at C5, C10, C13, C17 in cholesterol core is usually defined, but must be verified on the specific certificate.

2D description (generic for cholesterol conjugates; verify for this item):

• Polycyclic hydrophobic sterol backbone with a single polar substituent at C3 and an alkyl side chain at C17; the conjugated “HAPC” moiety is typically attached at the 3-position through a carbonate/ester/ether/urethane or via a linker.

Synthetic Utility

Item-specific reactions are not provided for this SKU.

General synthetic context for cholesterol conjugates (literature; not item-specific):

• Common linkages: carbonate, ester, ether, amide, and urethane at the cholesterol 3‑position; alternative strategies exploit click chemistry (CuAAC) via azido/alkyne-functionalized linkers on either the sterol or the partner molecule.
• Protecting groups: If multiple nucleophiles are present on the “HAPC” headgroup, Boc/CBz or silyl protections may be used prior to coupling to the sterol.
• Activation methods: Use p‑nitrophenyl carbonate or NHS carbonate/ester derivatives of cholesterol for efficient coupling to amines or alcohols under mild conditions; DMAP/DIPEA often employed.
• Purification: Sterol conjugates frequently require normal-phase silica with gradients of hexanes/EtOAc/CH2Cl2 and small MeOH percentages; reversed-phase prep HPLC (C18) with ACN/H2O + 0.1% formic acid can also be effective for amphiphilic products.
• Characterization: 1H/13C NMR in CDCl3, CD2Cl2, or CD3OD; HRMS (ESI/APCI) depending on polarity; IR to confirm carbonate/ester/amide bands; optical rotation where stereochemistry is defined.

Use as a building block:

• The conjugate can act as a hydrophobic handle in further functionalization (e.g., appending fluorophores, peptides, or targeting ligands) when residual handles (azide/alkyne/amine) are present.

Target Specificity

Not applicable. This product is a small molecule and not an antibody or affinity reagent. No antigen, epitope, clone, isotype, or species reactivity information applies. If the conjugate is used to bias membrane localization in biological experiments, such effects are non-specific and depend on formulation and context.

よくある質問

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.

How should this product be stored?

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

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

The CAS Number is 1027801-73-5, the molecular formula is C33H58N2O3, and the molecular weight is 530.83 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.