Gal-C4-Chol , CAS No.219850-70-1

CAS: 219850-70-1 Cat. No.: G1439990 Fórmula: C₄₀H₆₉N₃O₇S Peso molecular: 736.06

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

Gal-C4-Chol is a glycosylated cholesterol derivative. Gal-C4-Chol can be used as a ligand for asialoglycoprotein receptors ( ASGPR ) to prepare Galactosylated (Gal) liposomes. Gal-C4-Chol can be used to prepare simple lipid-based nanoparticles.

Specifications

Condições de armazenamento de armazenamento

Store at -20°C

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Nomes e identificadores

Peso molecular

736.06

Application Protocols

Tested application details are not specified for this item; refer to the CoA/Spec Sheet and SDS. No manufacturer-validated protocols are provided in the Product Data for SKU G1439990.

Guidance: Consult peer-reviewed literature for protocols on incorporating galactose–cholesterol conjugates into liposomes, supported bilayers, or nanoparticle coatings appropriate to your research system.

Biological Roles

Context (general; not product-specific claims): Galactose–cholesterol conjugates are research tools that integrate a hydrophobic sterol anchor with a galactosyl headgroup to study carbohydrate–protein interactions and membrane biology.

Key biological concepts (literature):

• Lectin recognition: β-D-galactose residues are ligands for several lectins, including the hepatic asialoglycoprotein receptor (ASGPR) and galectins. Displaying galactose at membrane surfaces enables investigation of avidity, multivalency, and receptor-mediated endocytic pathways in cell models.
• Membrane partitioning: The cholesteryl moiety inserts into lipid bilayers, often localizing to ordered domains (raft-like regions), which can influence receptor clustering and signaling readouts.
• Glycocalyx mimicry: Galactosylated lipids emulate features of natural glycolipids/glycoproteins, facilitating studies of cell adhesion, pathogen–host interactions, and immune lectin binding.
• Nanocarrier targeting (research context): Inclusion in liposomes or nanoparticles can modulate uptake in galactose-receptor–expressing cells in vitro, supporting mechanistic research on carbohydrate-mediated delivery pathways without implying clinical use.

Experimental considerations:

• Ligand density is critical; systematic variation (e.g., 0.5–10 mol%) helps map binding thresholds.
• Competitive inhibition with free D-galactose can be used to confirm lectin-specific uptake/binding in assays.
• Orientation and spacer length (C4 here, generically) affect accessibility of the sugar and can tune binding kinetics.

Note: All uses are for research only; no medical or clinical claims are implied.

Buffer Applications

This item is not a buffering reagent. It does not form defined pH buffer systems on its own. For experiments, hydrate or disperse Gal-C4-Chol in preselected biological buffers (e.g., PBS, HEPES) appropriate to your model system, often alongside helper lipids or surfactants. Refer to Solvent Selection and Reaction & Applications for formulation-oriented guidance.

Green Alternatives

While Gal-C4-Chol itself is the functional material, greener choices focus on solvents and processes used to dissolve and formulate it. The following are general, literature-based considerations (not product specifications):

Greener solvent options compared to traditional chlorinated solvents:

• Traditional choice: chloroform and dichloromethane are effective but hazardous and high-impact.
• Alternatives:
  • 2-Methyltetrahydrofuran (2-MeTHF): bio-based, good sterol solubility; may require gentle warming.
  • Cyclopentyl methyl ether (CPME): hydrophobic, low peroxide formation rate relative to THF; useful for film casting with small alcohol admixtures.
  • Ethyl acetate or isopropanol/ethyl acetate mixtures: safer profiles; solubility may be lower and require optimization.

Comparison (literature; qualitative):

• Solubility: CHCl3 > DCM ≳ THF > 2-MeTHF ≳ CPME > EtOAc (varies with conjugate and hydration state).
• Toxicity/Environment: EtOAc, 2-MeTHF, CPME generally preferred over CHCl3/DCM.

Process considerations:

• Minimize solvent volumes via concentrated stocks and efficient film-casting techniques.
• Use closed systems with cold traps to reduce emissions.
• Choose energy-efficient hydration (e.g., vortex + bath sonication) before resorting to probe sonication.

Trade-offs:

• Greener ethers may need longer dissolution times and slightly elevated temperatures.
• Residual solvent removal must be validated regardless of solvent choice (e.g., GC headspace checks).

Pharmaceutical Uses

No pharmacopeial status or excipient designation is provided for this item. Not specified for this item; refer to CoA/Spec Sheet.

General information for research formulation contexts (not product-specific claims and not for clinical use):

• Glycolipid additives like galactose–cholesterol conjugates are frequently explored in preclinical research to modulate cell interactions, colloidal stability, and uptake pathways of lipid-based carriers.
• Roles may include surface ligand presentation, membrane rigidity modulation (via the sterol core), and tuning of zeta potential when combined with charged helper lipids.
• Manufacturing considerations at research scale: solvent casting followed by hydration and extrusion; rigorous removal of organic solvents; analytical verification of composition by lipidomics.

Regulatory note: This product is for research use only. No claims are made regarding suitability for human or veterinary drug products.

Physical Properties

Item-specific properties (from 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.

Literature/general expectations for galactose–cholesterol conjugates (informational only, not product specifications):

• Physical state: typically solid or waxy solid at ambient temperature due to the sterol core; may appear as amorphous film or powder depending on preparation (literature).
• Solubility: generally soluble in chlorinated solvents (e.g., CHCl3, CH2Cl2), THF, and in alcohol/CHCl3 mixtures; poorly soluble in water and most aqueous buffers unless formulated in micelles or liposomes (literature).
• LogP: high (driven by sterol), but effective amphiphilicity arises from the pendant sugar (literature).
• Melting behavior: broad softening range rather than sharp MP is common for amphiphilic conjugates; thermal transitions can depend on hydration and prior thermal history (literature).
• Optical activity: chiral due to multiple stereocenters in both cholesterol and D-galactose; specific rotation varies with linkage chemistry and solvent (literature).

Practical notes (general):

• Films cast from chloroform/methanol can be readily hydrated to form vesicles or mixed micelles with helper lipids (literature).
• For analytical characterization, HRMS, 1H/13C NMR (including HSQC/HMBC), and IR (ester/ether signatures) are commonly used; TLC often requires sugar-sensitive stains (e.g., anisaldehyde or sulfuric acid) (literature).

Quality and Grades

Item-specific quality information:

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

Guidance on interpreting grades for similar materials (general; not specific to this SKU):

• Research-grade glycolipids are typically supplied at high organic purity suitable for formulation, bioconjugation, or surface assembly. If stated, “HPLC grade” refers to solvent quality, not the solid; for solids, terms such as “>95% (HPLC)” indicate chromatographic purity by area percent (literature).
• Stabilizers: Glycolipids rarely require added stabilizers; if present, stabilizers are disclosed on the CoA. Absence of stabilizers facilitates downstream coupling and analytical work.
• Impurities relevant to use: residual inorganic salts, protecting-group remnants, or partially deprotected sugars can affect binding to lectins and membrane behavior. Review the CoA for purity mode (HPLC/UPLC, NMR integral) and moisture content when available.

Recommended quality control upon receipt (general best practices):

• Record lot number and request CoA if not provided.
• Check identity by 1H NMR in CDCl3/CD3OD or DMSO-d6 mixtures; verify sugar resonances and sterol methyl patterns.
• For formulation-critical work, verify purity by LC-MS and assess water content by Karl Fischer if your application is hydration-sensitive.

Note: All item-specific specifications should be confirmed on the CoA/Spec Sheet for SKU G1439990.

Reaction and Applications

Manufacturer Applications: Not specified in the Product Data. The following are general research uses for galactose–cholesterol conjugates (literature; not product-specific claims):

• Lectin-targeted assemblies: Incorporation into liposomes, lipid nanoparticles, or micelles to display galactose on the surface for interaction with galactose-binding lectins such as the hepatic asialoglycoprotein receptor (ASGPR) in cell-based research models.
• Membrane engineering: Doping into supported lipid bilayers or giant unilamellar vesicles to modulate adhesion, cell recognition, or glycan-density-dependent phenomena.
• Surface functionalization: Immobilization onto hydrophobic surfaces or nanoparticles where the cholesteryl anchor ensures robust adsorption and the galactose headgroup mediates specific carbohydrate–protein interactions.
• Affinity capture and sensing: Presentation of galactosyl epitopes for lectin binding studies, SPR/biolayer interferometry, or microarray-like glycan display when co-assembled with helper lipids.

Practical tips (general):

• Co-formulate at low to moderate mol% (e.g., 1–10 mol% of total lipid) to balance ligand density and membrane integrity; optimize per system.
• Ensure thorough solvent removal (rotary evaporation + high vacuum desiccation) before hydration to avoid solvent artifacts.
• Use extrusion or probe sonication to control vesicle size; validate ligand incorporation by colorimetric sugar assays or LC-MS of extracted lipids.
• Avoid prolonged exposure to strong base or acid during formulation to minimize hydrolysis of linker functionalities.

Reaction Conditions

There are no item-specific reaction conditions provided in the Product Data. The following general conditions relate to formulating and assembling amphiphilic glycolipids (literature; not specifications):

• Thin-film hydration: Dissolve Gal-C4-Chol together with helper lipids (e.g., phosphatidylcholine, cholesterol, PEG-lipids as desired) in CHCl3:MeOH (2:1). Evaporate under reduced pressure to a dry film, apply high vacuum ≥2 h, then hydrate with buffered saline at 37–60°C while vortexing. Optional freeze–thaw cycles (5–10) improve lamellarity.
• Sonication/extrusion: Probe or bath sonication can reduce vesicle size; polycarbonate extrusion (50–200 nm pore sizes) yields monodisperse liposomes. Work cold for heat-sensitive cargo.
• Micelle assembly: For surfactant-assisted incorporation, dissolve in a minimal amount of DMSO or ethanol, inject into warm buffer with stirring above CMC of the co-surfactant, then dialyze to remove solvent.
• Surface assembly: For supported lipid bilayers, deposit small unilamellar vesicles on cleaned substrates (e.g., SiO2) and incubate to form continuous bilayers; verify by FRAP.

Analytical controls:

• Determine incorporation via phenol–sulfuric acid carbohydrate assay or LC-MS of extracted lipids.
• Assess size and PDI by DLS; zeta potential for surface charge; confirm galactose accessibility by lectin binding assays.

Adjust temperatures and times according to your lipid matrix; avoid extremes of pH that could hydrolyze linker chemistry.

Safety and Handling

Item-specific hazard information from Product Data:

• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• GHS Classification: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance for amphiphilic lipids/glycolipids (informational only; defer to SDS for this item):

• PPE: wear lab coat, safety glasses, and appropriate chemically resistant gloves when handling solids and organic solvent solutions.
• Handling: avoid dust generation; weigh in a fume hood. Prepare solutions in compatible organic solvents (e.g., CHCl3, MeOH, THF) with adequate ventilation.
• Incompatibilities: strong oxidizers and strong acids/bases may degrade the sugar or cleave linkages. Prolonged exposure to moisture can promote hydrolysis for ester/carbonate linkages (literature).
• Thermal sensitivity: minimize prolonged heating; use gentle warming (<50–60°C) only as needed to dissolve or cast films (literature).
• First aid (general): in case of skin/eye contact, rinse with water for at least 15 minutes and remove contaminated clothing; if inhaled, move to fresh air; if ingested, rinse mouth—seek medical attention in all cases. Always consult the SDS for authoritative instructions.
• Waste: dispose according to institutional guidelines for organic chemical waste; avoid release to drains.

Note: No peroxide-forming risk is typically associated with the solid itself, but many handling solvents (ethers, THF) can form peroxides—manage those solvents appropriately (literature).

Solvent Selection

Applicability: As an amphiphilic galactose–cholesterol conjugate, solvent choice strongly influences handling, film formation, and formulation.

General solvent behavior for this class (literature; not product specifications):

• Nonpolar/halogenated: high solubility in chloroform and dichloromethane; useful for thin-film casting and chromatography.
• Polar aprotic: moderate solubility in THF, dioxane; sometimes in DMF/DMSO depending on linkage and hydration state.
• Alcohols: MeOH/EtOH co-solvents enhance dissolution with CHCl3 for stock solutions (e.g., 2:1 CHCl3:MeOH).
• Water/buffers: typically insoluble; disperses upon co-formulation with helper lipids and surfactants to form liposomes or micelles.

Selection guidance (general):

• For stock preparation: use CHCl3 or CH2Cl2, optionally with MeOH. Filter through PTFE syringes if needed.
• For lipid film hydration: cast from CHCl3:MeOH, evaporate under reduced pressure, desiccate, then hydrate with buffer above the lipid transition temperature.
• For analytical HPLC: normal-phase methods (hexanes/IPA/EtOAc) or reversed-phase (ACN/H2O with MeOH modifiers) may be used with ELSD/charged aerosol detection.

Comparison (literature):

• CHCl3 vs THF: CHCl3 often dissolves sterols more readily; THF is more polar and can better co-dissolve sugars, aiding homogeneous films.
• DMSO/DMF: enable aqueous injection as DMSO/DMF stocks but may affect downstream bioassays; dilute thoroughly.

Always verify solvent compatibility with your application and remove residual solvent rigorously for biological studies.

Storage and Reconstitution

Item-specific instructions (from Product Data):

• Storage Conditions: Store at -20°C.
• Shipped In: Ice chest + Ice pads.

General guidance for this class of materials (informational; not product specifications):

• Protect from light and moisture. Store tightly capped under inert gas or in a desiccator to minimize hydrolysis of labile linkages.
• For long-term storage, keep as a dry solid or as a thin film rather than in solution. Avoid repeated warming/cooling cycles.
• If preparing stock solutions, use dry, oxygen-free solvents (e.g., CHCl3, CH2Cl2, or CHCl3:MeOH). Aliquot and store frozen to limit freeze–thaw; verify stability periodically by TLC or LC-MS.
• Reconstitution for formulation: Dissolve the weighed amount in suitable organic solvent, cast a thin film, remove solvent thoroughly (rotavap + high vacuum), then hydrate with buffer prewarmed to the desired temperature while vortexing. Optional sonication/extrusion to achieve target size.
• Working dispersions: Use promptly or store at 2–8°C for short periods; monitor for aggregation. For longer storage, freezing of liposomes is generally discouraged unless cryoprotectants and validated protocols are used.

Always follow the SDS and the lot-specific CoA for definitive instructions for SKU G1439990.

Structure and Identity

Overview: Gal-C4-Chol is commonly understood in research as a galactose–cholesterol conjugate linked through a short C4 (butyl) spacer, yielding an amphiphilic glycolipid useful for lectin-directed delivery and membrane engineering.

Item-specific identifiers (from Product Data):

• CAS: 219850-70-1
• 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.

Structural features (general/literature description of class):

• Contains a sterol core (cholesterol scaffold: tetracyclic fused ring system with a 3β-substituent and an aliphatic side chain) providing a hydrophobic anchor into lipid phases (literature).
• Incorporates a D-galactose headgroup (polyhydroxylated pyranose) conferring hydrophilicity and lectin-recognition capability (literature).
• Spacer: C4 aliphatic linker between sugar and sterol to reduce steric hindrance and enhance presentation of the galactosyl epitope at interfaces (literature).

2D structure described in words (literature-type depiction):

• Left side: tetracyclic cholestane rings (A–D) with the isooctyl side chain at C17; typical 3β-substitution point used for conjugation.
• Linker: a four-carbon aliphatic chain joining the 3β-position of cholesterol to the sugar moiety via an ester or ether/urethane-type bond depending on synthesis (exact connectivity for this catalog item is not specified here).
• Right side: a six-membered galactopyranose ring with equatorial hydroxyls characteristic of β-D-galactose presentation.

Synthetic Utility

Although typically used as a functional amphiphile rather than as a reactive intermediate, galactose–cholesterol conjugates offer utility in assembling complex biomimetic systems and surfaces.

Utility themes (general; literature):

• Modular glycan display: Serves as a ready-to-use galactosyl presenting unit with a built-in hydrophobic anchor, obviating on-surface glycosylation chemistry.
• Mixed monolayers and bilayers: Co-assembles with phospholipids, sphingolipids, and sterols to build glycolipid-rich membranes for biophysical studies (e.g., fluorescence recovery, SPR).
• Nanoparticle functionalization: Adsorption onto hydrophobic nanoparticles (e.g., polystyrene, some inorganic cores with hydrophobic coatings) to introduce galactose at the interface.
• Immobilization scaffolds: The sterol core’s strong membrane affinity enables stable insertion into living cell membranes for transient surface modification in cell-based assays.

Retrosynthetic and derivatization considerations (general):

• Linkage chemistry (ester, carbonate, carbamate, ether) affects stability to hydrolysis and enzymatic cleavage; choice is application-driven.
• The C4 spacer is a compromise between accessibility and membrane perturbation; longer spacers increase reach but may reduce packing order.
• Post-assembly conjugation: If free hydroxyls on the sugar are available, further derivatization (e.g., boronate affinity tagging) can be conducted at the formulation stage, mindful of selectivity and stability.

Note: No item-specific reactive handles are specified; consult the CoA/Spec Sheet for functional group details.

Target Specificity

Item-specific target information (antibody/bioreagent context) is not applicable. No antigen, clone, isotype, or species reactivity data are provided in the Product Data for SKU G1439990.

General note (informational only): In research, galactose-displaying surfaces can interact with galactose-binding lectins (e.g., ASGPR, certain galectins). However, such interactions are assay- and context-dependent and are not guaranteed specifications of this item.

Perguntas frequentes

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 219850-70-1, the molecular formula is C40H69N3O7S, and the molecular weight is 736.06 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.