Cholicamideβ (GMP) , CAS No.C1417556

CAS: C1417556 Cat. No.: C1417556 Formula: C₅₅H₉₄N₂O₆ Molecular Weight: 879.34

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Cholicamideβ (GMP) is a GMP grade of Cholicamideβ. Cholicamideβ (compound 6) is a self-assembling, small molecule, cancer vaccine adjuvant. Cholicamideβ can form virus-like particles with low cytotoxicity. Cholicamideβ, upon binding to peptide antigens, enhances antigen presentation by dendritic cells and induces antigen-specific T cells. Cholicamideβ can induce apoptosis and necrosis.

Specifications

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

Molecular Weight

879.34

Application Protocols

No validated biological assay or analytical protocols are provided for this SKU. As a general guide for small-molecule handling in research:

• Stock preparation (general)

  • Prepare concentrated stocks in dry DMSO or ethanol (e.g., 10–50 mM), then dilute into assay media while maintaining final organic content below assay tolerance (commonly ≤0.5–1% v/v DMSO).

• Solubilization aids (general)

  • If needed, use gentle warming (≤40 °C) and sonication. Consider cyclodextrins or nonionic surfactants to enhance apparent aqueous solubility.

• Analytical QC (general)

  • Verify identity and purity on receipt using your in-house LC–MS/HPLC method aligned to your acceptance criteria. Compare to vendor CoA.

For any application-specific protocol (e.g., transporter uptake assays, micelle characterization), consult primary literature for cholicamide derivatives and adapt to your instrument and regulatory environment.

Biological Roles

No biological activity data specific to this SKU are provided. The following contextual information is general for bile-acid derivatives in research.

• Bile acid scaffold (literature/general)

  • Cholic acid derivatives participate in lipid solubilization and micelle formation in biological systems due to their amphiphilic steroidal framework.
  • Natural bile acids act as signaling molecules in metabolic pathways and can interact with nuclear (e.g., FXR) and membrane (e.g., TGR5) receptors; whether an amide derivative retains such interactions depends on structural details not specified here.

• Research relevance

  • Used as tools to study bile acid transporters (NTCP/SLC10A1, ASBT/SLC10A2) and enterohepatic circulation in in vitro systems.
  • Serve as carriers or targeting moieties in conjugates designed to probe hepatobiliary uptake in cell models.
  • Micelle formation can enhance the apparent solubility of hydrophobic analytes in enzymology or spectroscopy experiments.

• Biophysical properties (general)

  • Critical micelle concentration (CMC) and aggregation number vary widely with substitution pattern and medium; consult primary literature for the exact derivative when designing experiments.

Note: This product is for research use only. No claims are made regarding biological efficacy, safety, or suitability for diagnostic or therapeutic applications.

Buffer Applications

Cholicamideβ is not a classical buffering reagent. It does not constitute a defined acid–base conjugate pair with a narrow pKa window suited for pH control in typical biochemical buffers.

• Practical guidance
  • If aqueous use is required, prepare buffers with standard systems (e.g., phosphate, HEPES, Tris) and dissolve the compound using minimal co-solvent (DMSO or ethanol) or mild surfactants as needed.
  • Verify that the chosen buffer and co-solvent do not precipitate the compound upon dilution; add organic co-solvent slowly with mixing.

For pH control, use established buffers and consult the CoA/Spec Sheet for any item-specific solubility or compatibility notes.

Green Alternatives

When selecting solvation or processing conditions for cholicamide-class compounds, greener choices can reduce environmental and safety burdens. Item-specific constraints are not provided; the following are general, literature-based considerations.

• Solvent alternatives (general)

  • Replace DMF/NMP with safer polar aprotics where feasible: propylene carbonate (PC), dimethyl sulfone, or Cyrene (dihydrolevoglucosenone) depending on reaction compatibility.
  • Use bio-based alcohols (ethanol, isopropanol) instead of methanol or chlorinated solvents for extractions and crystallizations.
  • Favor aqueous systems aided by co-solvents (≤10% ethanol or DMSO) or benign surfactants for dissolution in assays.

• Purification

  • Minimize chlorinated solvent use (e.g., DCM) during workups; employ ethyl acetate/IPA/heptane systems or supercritical CO2 where compatible.

• Energy and waste

  • Employ room-temperature couplings (enzymatic or organocatalytic acylations) for hydroxyl derivatization to reduce heating and byproducts.

• Comparison snapshot (general)

  • DMF vs. Cyrene: Cyrene offers reduced reproductive toxicity concerns and is biodegradable; viscosity and basicity differ, so reaction rates/solubility may change.
  • DCM vs. EtOAc: EtOAc is less toxic and derived from ethanol/acetic acid; may require different chromatographic gradients.
  • Methanol vs. Ethanol: similar polarity; ethanol has lower chronic toxicity and can be bio-sourced.

Always confirm that greener substitutes meet your process performance and quality requirements for this GMP-designated material.

Pharmaceutical Uses

No pharmacopeial status or formulation role is provided for this SKU. The following points are general, literature-based considerations for bile-acid derivatives in formulation science. This product is for research use only and not for clinical use.

• Potential roles (general)

  • Solubilization/dispersion aid: amphiphilic steroidal frameworks can assist in dissolving hydrophobic actives in pre-formulation studies.
  • Permeation/absorption enhancement studies: bile-acid derivatives are researched as excipient candidates or targeting ligands for hepatobiliary delivery in in vitro models.
  • Conjugation handle: amide- or hydroxyl-bearing scaffolds enable pro-moiety or polymer conjugation to modulate disposition in research settings.

• Considerations

  • Excipient compatibility, impurity profiles, endotoxin/bioburden, and elemental impurities must be established for regulated uses; these are Not specified for this item; refer to CoA/Spec Sheet.
  • Stability across pH and temperature, as well as interaction with common excipients (polymers, surfactants), should be characterized in your formulation screen.

• Documentation

  • If considering this GMP-designated material for process development, request detailed CoA, stability data, and supply chain traceability. Establish incoming QC methods (e.g., HPLC purity, water content) aligned to your internal specifications.

Physical Properties

Item-specific physicochemical data are not provided in the Product Data.

• Item-specific values

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting point: Not specified for this item; refer to CoA/Spec Sheet.
  • Boiling point: Not applicable (decomposes before boiling; literature expectation for steroidal amides).
  • Density: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • LogP/logD: Not specified for this item; refer to CoA/Spec Sheet.
  • pKa(s): Not specified for this item; refer to CoA/Spec Sheet.
  • Refractive index: Not applicable (solid expected; literature for class).

• Literature/general expectations for bile-acid amides (not item-specific)

  • Physical state: typically solid powders.
  • Solubility profile: often sparingly soluble in water at neutral pH; improved solubility in polar organics (DMSO, DMF, methanol, ethanol). Micelle formation or inclusion with cyclodextrins can enhance apparent aqueous solubility.
  • Amphiphilicity: multiple hydroxyls and an amide confer H-bonding; steroid core drives hydrophobic interactions.
  • Thermal behavior: steroidal amides typically exhibit high melting points with broad thermal transitions and can char/decompose rather than distill.

Always verify item-specific data (solubility, MP, water/metal limits, UV cutoff) on the CoA/Spec Sheet for this SKU.

Quality & Grades

• Grade designation (from Product Data)

  • Listing: “Cholicamideβ (GMP)”. While detailed grade specifications are not provided, the GMP tag indicates manufacture under Good Manufacturing Practice controls appropriate for non-clinical/industrial processes. No medical or clinical claims are made; for research use only.

• What GMP generally implies (literature/general)

  • Documented batch records, change control, and traceability of raw materials.
  • Qualified equipment and validated/qualified processes where applicable.
  • Defined specifications with in-process/finished product testing (identity, purity, residual solvents/impurities as applicable).
  • Robust QA/QC release and retention sample program.

• What is NOT specified for this item (do not assume)

  • Purity assay, residual solvent limits, water/peroxide/metal limits, microbial/bioburden, endotoxin, or specific stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
  • Exact regulatory scope (e.g., GMP for API vs. excipient vs. ancillary material): Not specified; confirm intended use with QA and the CoA.

• Practical considerations for users

  • If this material supports regulated workflows (e.g., manufacturing intermediates, assay reagents), request the Quality Agreement/Questionnaire and current CoA.
  • For analytical methods, obtain the vendor’s release methods or typical chromatographic conditions to harmonize your incoming QC (identity/purity).
  • If you need low-UV, low-fluorescence, bioburden control, or elemental impurity limits, specify these at PO and confirm on the CoA.

Reaction & Applications

• Research applications (general for cholic acid amide derivatives)

  • Amphiphile/micelle former for solubilizing hydrophobic analytes in analytical or biophysical studies.
  • Probe scaffold: bile-acid amides can be conjugated to fluorophores, affinity tags, or linkers for transporter/receptor studies (e.g., bile acid transporters, FXR/TGR5 pathway investigations) in a research setting.
  • Supramolecular chemistry: template for host–guest assemblies, mixed micelles with nonionic surfactants, and chiral microenvironments.
  • Materials/colloid science: modifier for nanoparticle surfaces to tune hydrophobicity and interfacial behavior.

• Synthetic/derivatization use (general)

  • Hydroxyl-selective transformations: acylation (Ac2O, acyl chlorides), silylation (TBDMS-Cl, TMS-Cl), carbonate formation, and selective oxidation to carbonyls (Swern, Dess–Martin) to build libraries.
  • Side-chain chemistry: if the amide is primary (–CONH2), N-acylation, N-alkylation (via activated derivatives), or conversion to ureas/carbamates is feasible; confirm amide substitution on the CoA.
  • Conjugation: NHS-ester, CDI, or EDC/NHS strategies on partner molecules to attach via the amide nitrogen or remaining hydroxyls (indirectly, through carbonate/carbamate linkers).

• Practical tips

  • Rigorous drying of polar aprotic solvents (DMF/DMSO) is beneficial for reproducible coupling.
  • Use stoichiometric bases with care to avoid undesired transacylation or elimination on the steroid core; mild conditions (DMAP, pyridine) often suffice for acylations.
  • Monitor reactions by LC–MS with ESI positive mode; bile-acid derivatives ionize well under soft conditions.

Note: No item-specific application data were provided. The above reflects general literature practices for bile-acid amide scaffolds.

Reaction Conditions

No item-specific reactivity data are provided. The following literature-based conditions are commonly used for derivatizing bile-acid amide scaffolds and are offered as general guidance only.

• Hydroxyl acylation/etherification (general)

  • Solvent: dry dichloromethane, pyridine, or DMF.
  • Reagents: acyl chlorides/anhydrides with catalytic DMAP; for etherification, alkyl halides with mild base (K2CO3, Cs2CO3) in DMF.
  • Temperature: 0 °C to room temperature; warm as needed to drive sluggish reactions.
  • Workup: aqueous quench, extraction with EtOAc, silica chromatography with hexane/EtOAc gradients.

• Carbamate/carbonate formation (general)

  • CDI or triphosgene for activation; alcohol/amine nucleophiles appended under mild base.
  • Solvent: dry THF, DCM, or DMF; 0–25 °C.

• Amide N-functionalization (if –CONH2 is present; confirm on CoA)

  • N-acylation with anhydrides or activated esters in pyridine or DCM (DMAP-catalyzed); avoid strong bases that may cause elimination.
  • Urea formation via isocyanates in DCM or THF at 0–25 °C.

• Oxidation of secondary alcohols (general)

  • Dess–Martin periodinane (DCM, rt) or TEMPO/bleach (biphasic, pH-controlled) to introduce ketones for further elaboration.

• Analytical monitoring

  • LC–MS (ESI+) and TLC with anisaldehyde/sulfuric stains help visualize steroidal products.

These conditions are illustrative. Optimize stoichiometry, temperature, and time based on small-scale trials and the specific substitution pattern of your material.

Safety & Handling

Safety details specific to this SKU are not listed in the Product Data.

• GHS information (item-specific)

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements (H-codes): Not specified for this item; refer to SDS.
  • Pictograms and classification: Not specified for this item; refer to SDS.

• General safety guidance for bile-acid derivatives (literature/general)

  • Avoid generation of dust/aerosols; handle in a chemical fume hood.
  • Recommended PPE: lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Consider respiratory protection if dust is unavoidable and ventilation is inadequate.
  • First aid overview: if inhaled, move to fresh air; for skin/eye contact, rinse with water for ≥15 minutes and remove contaminated clothing; if ingested, rinse mouth and seek medical attention. Always follow institutional procedures.
  • Incompatibilities: strong oxidizers; strong acids/bases may promote degradation (hydrolysis/oxidation). Avoid prolonged exposure to elevated temperatures.

• Storage and transport (from Product Data)

  • Storage: Store at −20°C.
  • Shipping: Shipped in an ice chest with ice pads to maintain a cold chain.

• Waste disposal

  • Dispose of in accordance with local, regional, and national regulations for organic laboratory chemicals. Do not release to the environment.

Authoritative safety information resides in the product SDS. Always consult the SDS before use.

Solvent Selection

This compound class (bile-acid amides) is amphiphilic. Item-specific solubility data are not provided, so the following are general, literature-based considerations to guide solvent choice.

• Polarity and miscibility (literature/general)

  • Frequently soluble in polar aprotic solvents: DMSO, DMF, NMP.
  • Often soluble to moderately soluble in polar protic solvents: methanol, ethanol, isopropanol.
  • Aqueous media: intrinsic solubility at neutral pH can be low to moderate; apparent solubility can be enhanced by co-solvents (≤10–20% v/v alcohols or DMSO), complexation (cyclodextrins), or formation of mixed micelles with nonionic surfactants.
  • Nonpolar solvents (hexanes, toluene) generally poor due to multiple hydroxyls and amide functionality.

• Practical selection tips (general)

  • For stock solutions in screening libraries, DMSO (anhydrous) at 10–50 mM is commonly used; filter-sterilize if required by workflow.
  • For biophysical assays, consider ethanol or ethanol/water to minimize DMSO content; titrate in slowly to avoid local supersaturation.
  • For synthetic derivatization, use dry DMF/DMSO with appropriate bases/coupling reagents; for protection/deprotection steps, choose solvents compatible with acid- or base-labile groups on the steroid scaffold.

• Comparison (general)

  • DMSO: highest solvating power; can affect bioassays at >1% v/v.
  • Methanol/ethanol: greener and volatile; may need warming/sonication.
  • Aqueous buffers with co-solvent/surfactant: enable biological testing while keeping organic content low.

Verify exact solubility and compatibility for this SKU on the CoA/Spec Sheet before finalizing solvent systems.

Storage & Reconstitution

• Storage (from Product Data)

  • Store at −20 °C. Keep container tightly closed. Protect from moisture and prolonged exposure to light and elevated temperatures.
  • Shipping: supplied in an ice chest with ice pads to maintain a cold chain.

• Stability considerations (general)

  • Bile-acid amide scaffolds are generally stable solids when dry and cold. Hydrolysis/oxidation may occur under strongly acidic/basic or oxidative conditions; minimize freeze–thaw and exposure to humid air.

• Reconstitution (general guidance; not item-specific)

  • Solvents: DMSO, DMF, ethanol, or methanol are typical starting points. Begin with small volumes and increase gradually with vortex/sonication.
  • Suggested stock concentrations for screening libraries: 10–50 mM in dry DMSO. Filter through 0.22 µm if particulate persists and sterility is required.
  • For aqueous use: dilute DMSO/ethanol stocks into buffered media slowly with vigorous mixing; consider co-solvent limits of your system (e.g., keep DMSO ≤1% v/v).

• Packaging and aliquoting (general)

  • Upon first opening, aliquot under dry inert gas if possible and re-freeze at −20 °C to reduce headspace moisture and repeated freeze–thaw.

Item-specific solubility, stability, and re-test dates are Not specified for this item; refer to CoA/Spec Sheet for definitive guidance.

Structure & Identity

Brief overview: Cholicamideβ (GMP) is supplied as a research-grade bile-acid amide derivative. Item-specific structural identifiers are not provided in the Product Data.

• Item-specific identifiers (from Product Data)

  • CAS: C1417556 (catalog/placeholder identifier as provided)
  • 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 (literature/general for “cholicamide” class)

  • Cholicamide is commonly understood as the primary carboxamide of cholic acid, retaining the steroidal cholane core (tetracyclic fused cyclopentanophenanthrene) and multiple hydroxyl groups on the A/B rings while converting the terminal C-24 carboxyl of the side chain to an amide.
  • The scaffold is amphiphilic: hydrophobic steroid nucleus + polar hydroxyls and an amide at the side chain.
  • Cholic acid in nature bears 3α,7α,12α-hydroxyls; specific stereochemistry and any “β” designation for this catalog item are not specified in the Product Data and should be confirmed on the CoA.

• 2D structure description (literature/general)

  • Four fused rings (A–D), typically trans-fused steroid framework; three hydroxyl substituents on the ring system; side chain terminating in –CONH2 (amide). The amphiphilic topology enables self-assembly/micellization in suitable media.

Note: For the exact identity parameters applicable to this SKU (isomer designation, stereochemistry, counter-ions, and any protecting groups), consult the item’s CoA/Spec Sheet.

Synthetic Utility

Cholicamide-class compounds serve as versatile scaffolds in synthesis due to their dense, stereochemically rich steroid core and multiple functional handles.

• Functional handles (general)

  • Hydroxyl groups (typically three on cholic acid derivatives): enable selective acylation, etherification, carbonate/carbamate formation, and oxidation/reduction sequences.
  • Amide at C-24 side chain: can participate in N-acylation, urea/carbamate formation, or be leveraged for hydrogen bonding in supramolecular design. If the amide is substituted, scope may differ—confirm on the CoA.

• Library generation

  • Positional selectivity can be controlled using protecting groups (TBDMS, TBS, TMS, benzyl) and acylation catalysts (DMAP, pyridine) to access mono-, di-, or tri-substituted derivatives.
  • Late-stage diversification via carbonate/carbamate linkers allows installation of dyes, affinity tags, or PEGs for bioconjugation studies.

• Retrosynthetic value

  • The bile-acid framework offers a chiral, rigid hydrophobic surface; appending polar groups creates amphiphiles with tunable CMC and aggregation behavior—useful in materials chemistry and delivery research.

• Analytical considerations

  • LC–MS (ESI+) and HRMS readily confirm modifications; 1H/13C NMR shows characteristic steroidal patterns (multiplicity-rich A/B ring region) and amide carbonyl around 170–175 ppm (13C, literature/general).

Note: No item-specific reactivity or impurity profile is provided. Verify compatibility with planned reagents/conditions on small scale first.

Target Specificity

Not applicable. This product is a small-molecule bile-acid amide derivative, not an antibody or affinity reagent. No antigen/epitope, clone, isotype, or species-reactivity information applies.