OH-C-Chol , CAS No.496801-51-5

CAS: 496801-51-5 Cat. No.: O1439878 PubChem CID: 102032621

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

OH-C-Chol is a cationic liposome that serves as a siRNA delivery vehicle. OH-C-Chol (LP-C) and OH-NC-Chol (LP-NC)/siRNA complexes (lipoplexes) showed better performance than NP-C and NP-NC/siRNA complexes (nanocomplexes), respectively. ) greater gene silencing effect.

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

Canonical Smiles

CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)NCCNCCO)C)C

IUPAC Name

[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-(2-hydroxyethylamino)ethyl]carbamate

InChIKey

IVKGTZVIOSLOAM-PTHRTHQKSA-N

INCHI

1S/C32H56N2O3/c1-22(2)7-6-8-23(3)27-11-12-28-26-10-9-24-21-25(37-30(36)34-18-17-33-19-20-35)13-15-31(24,4)29(26)14-16-32(27,28)5/h9,22-23,25-29,33,35H,6-8,10-21H2,1-5H3,(H,34,36)/t23-,25+,26+,27-,28+,29+,31+,32-/m1/s1

Isomeric SMILES

C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OC(=O)NCCNCCO)C)C

PubChem CID

102032621

Application Protocols

No item-specific, validated protocols are provided. The following general procedures for sterol-like compounds are offered as practical starting points (research use only):

1. Stock solution preparation

• Dissolve the compound at 10–50 mM in anhydrous DMSO or ethanol.
• Vortex and, if needed, warm gently (≤40–50 °C) to aid dissolution.
• Filter through a 0.22 µm PTFE syringe filter for assay use.

2. Liposome incorporation (thin-film hydration)

• Co-dissolve phospholipids and the sterol derivative in CHCl3/MeOH (2:1 v/v).
• Evaporate to dryness on a rotary evaporator, then apply high vacuum ≥2 h.
• Hydrate with warm buffer (e.g., PBS, 50–60 °C) to desired lipid concentration.
• Vortex, then extrude through polycarbonate membranes (100–200 nm) for size control.

3. Cell culture dosing

• Prepare working solutions by adding the DMSO stock dropwise into serum-containing medium with rapid mixing.
• Keep final DMSO ≤0.5–1% v/v; inspect for precipitation.

4. Surface insertion on supported bilayers

• Flow a buffered solution containing the sterol derivative (delivered from ethanol stock at ≤1% final) over preformed bilayers; rinse to remove excess.

Always confirm compatibility and stability for OH-C-Chol from the CoA/SDS before adopting any protocol.

Biological Roles

No biological role is specified for this item. The following summarizes general, literature-level roles of cholesterol-based molecules in biology (not item-specific and not clinical claims).

• Membrane component: Cholesterol is a major eukaryotic membrane sterol, modulating bilayer order, thickness, and permeability. It promotes liquid-ordered domains (rafts) in combination with sphingolipids.
• Signal regulation: Oxysterols and other cholesterol metabolites can act as ligands for nuclear receptors (e.g., LXR) and influence cholesterol homeostasis. Substitutions on the sterol core can dramatically change receptor interactions.
• Transport and trafficking: Cellular uptake and efflux pathways (LDLR-mediated endocytosis, NPC1/2 transport, ABCA1-mediated efflux) manage sterol distribution. Derivatized sterols are often used as tracers in these pathways.
• Biosynthesis precursor: Cholesterol sits downstream of the mevalonate pathway; enzymatic transformations lead to bile acids, steroid hormones, and oxysterols.

Application relevance:

• Cholesterol-like probes can be used to study domain formation, membrane insertion, and interactions with cholesterol-binding proteins (e.g., caveolin, NPC1), provided the substituents preserve bilayer affinity.

Caveats:

• Structural modifications may alter membrane partitioning and protein affinity; validate each derivative’s behavior experimentally.
• Working concentrations should be optimized to avoid non-physiological aggregation or micelle formation in biological media.

Buffer Applications

This product is a hydrophobic sterol-like small molecule and is not a buffering agent. There are no item-specific buffer recipes or pH ranges.

• Not typically used to set or maintain pH.
• For biological assays, stocks are commonly prepared in DMSO or ethanol and then diluted into aqueous buffers (PBS, HEPES, Tris) with vigorous mixing to avoid precipitation.
• When incorporating into liposomes or supported bilayers, hydrate dried lipid films with the desired buffer (e.g., PBS, HEPES), then extrude/sonicate to achieve the target size distribution.

For pH control, use established buffer systems (e.g., HEPES pH 7.2–7.6, phosphate pH 6–8, Tris pH 7–9) appropriate to your assay—this compound does not substitute for those reagents.

Green Alternatives

While sterol derivatives often require strong organic solvents for dissolution and processing, greener choices can be adopted where compatible with the chemistry.

Comparison (general guidance):

• Chlorinated solvents (CHCl3, DCM)

  • Pros: Excellent solvency for sterols; rapid evaporation; common in lipid film formation.
  • Cons: Toxicity, environmental and regulatory burdens.
  • Greener alternatives: Ethyl acetate (EtOAc), cyclopentyl methyl ether (CPME), dimethyl carbonate (DMC) when solubility allows.

• Aromatics (toluene)

  • Pros: Good solvency; thermal stability for some reactions.
  • Cons: VOC concerns; worker exposure limits.
  • Alternative: p-cymene or anisole for high-temp needs; still assess solvency.

• Polar aprotics (DMF, NMP)

  • Pros: Strong solvency; useful for coupling reactions or stock solutions.
  • Cons: Reprotoxic concerns (NMP), difficult removal.
  • Alternative: Cyrene or GBL (with caution), or DMSO (less hazardous but may affect bioassays).

• Ethers (THF)

  • Pros: Versatile, good solvency.
  • Cons: Peroxide formation; flammability.
  • Alternative: 2-MeTHF or CPME, offering better safety and biorenewable sourcing.

Best practices:

• Use the minimal effective solvent volume; recover and recycle where possible.
• Favor ethanol or isopropanol for preparing biological working stocks when solubility permits.
• For chromatographic purification, consider heptane/EtOAc or heptane/IPA systems over chlorinated eluents.

Note: Verify actual solubility/compatibility for OH-C-Chol before adopting alternatives.

Pharmaceutical Uses

No pharmacopeial status or item-specific excipient role is provided. The following are general, non-clinical notes on the role of cholesterol-type compounds in formulation science (research/manufacturing context only, no therapeutic claims).

• Liposomes and LNPs: Cholesterol is a standard component that increases bilayer rigidity, reduces permeability, and improves colloidal stability. Derivatives can fine-tune membrane properties or provide attachment points for targeting ligands.
• Solid dispersions and nanoparticles: Hydrophobic sterols may be used to adjust matrix hydrophobicity or as stabilizing co-components in experimental delivery systems.
• Topical/dermal bases (R&D): Sterol derivatives contribute to barrier properties and consistency; exact suitability depends on substitution and purity.

Formulation considerations (general):

• Confirm compatibility with other lipids (PC, PE, PEG-lipids) and the process (ethanol injection, microfluidics, thin-film hydration).
• Validate residual solvent limits if chlorinated solvents are used in film formation.
• Assess oxidative stability; include antioxidants if appropriate and permissible for the intended research use.

Note: Any use is for research and development only, as stated: For research use only.

Physical Properties

Item-specific physico-chemical specifications are not provided and should be confirmed on the CoA.

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

General/literature guidance for cholesterol-type derivatives (not item-specific):

• Physical state: Typically crystalline solid or waxy solid at room temperature, hydrophobic.
• Solubility profile: Very low in water; soluble in many organic solvents (e.g., chloroform, dichloromethane, THF, toluene) and often in alcohols (EtOH, i-PrOH) or polar aprotic media (DMSO, DMF), depending on substitution.
• Partitioning: High lipophilicity (positive logP) common to sterols; exact logP depends on substituents.
• Melting/boiling: Cholesterol melts ~148–150 °C (literature). Derivatives vary widely by functional group.
• Spectral characteristics: Sterol alkene typically shows UV absorption in the deep UV; derivatives may have altered UV due to conjugation—confirm before HPLC/UV.

Practical notes:

• Prepare stock solutions in a compatible organic solvent and quantify gravimetrically.
• If forming films (e.g., for liposome prep), use azeotrope-compatible solvents (CHCl3/MeOH) and evaporate under reduced pressure, then high vacuum to remove residuals.
• Always verify specific handling parameters (e.g., solubility limits, refractive index) for this SKU from the CoA.

Quality & Grades

Item-specific grade, purity, and stabilizer information were not provided in the product data.

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

General guidance on grades (context for cholesterol-type compounds):

• Research grade: Common for screening libraries and biochemical studies; suitable for most synthetic and discovery workflows.
• Analytical/HPLC grade solvents (context): If this compound will be analyzed by HPLC/UPLC, use low-UV-absorbance mobile phases and high-purity solvents to minimize baseline noise.
• Chromatographic suitability: For compounds with strong hydrophobicity, gradient RP-HPLC with higher organic content or normal-phase systems may be preferable; purity assessment often benefits from ELSD/charged aerosol detection in addition to UV.

What to check on the CoA for this SKU:

• Verified structure (NMR, HRMS), % purity and assay method, water content (Karl Fischer) if applicable, residual solvent levels, and any stated limits on peroxides/oxidative impurities.
• Recommended storage conditions and retest/expiry dating.

If a stabilizer is listed on the CoA (e.g., BHT for unsaturated lipids), consider its impact on downstream assays and remove if necessary by preparative chromatography or repeated co-evaporation.

Reaction & Applications

Manufacturer application specifics were not provided. Below are common research applications for cholesterol-type small molecules (general literature guidance; verify suitability for this specific SKU).

• Membrane and lipid research: Cholesterol derivatives are used to modulate membrane fluidity, raft formation, and order parameters in model membranes and liposomes. They can serve as anchors for functional moieties (fluorophores, peptides, PEG) to localize payloads to membranes.
• Formulation excipient: Cholesterol is a canonical component of liposomes and lipid nanoparticles (LNPs), improving membrane rigidity and stability.
• Surface chemistry: Cholesterol groups can drive insertion into lipid bilayers on supported membranes or living cells, enabling temporary display of ligands.
• Chemical biology probes: When bearing reporter or bioorthogonal groups, sterol derivatives can be used for trafficking studies, click labeling, or cholesterol uptake assays.

Practical tips:

• For vesicle prep, co-dissolve lipids and this sterol derivative in CHCl3/MeOH, dry thoroughly (rotary evaporation + high vacuum), then hydrate and extrude.
• For cell studies, pre-dilute DMSO stocks into serum-containing medium to minimize precipitation; titrate to find the maximal soluble concentration without micelle formation.
• For solid-state uses (films, coatings), warm gently (≤50 °C) to assist dissolution in nonpolar solvents; avoid prolonged heating to limit oxidation of unsaturated sites.

Note: The exact activities or use cases depend on the specific substituents present in OH-C-Chol; confirm with the CoA/SDS.

Reaction Conditions

General literature-level conditions for common transformations on cholesterol-type scaffolds (not item-specific; verify compatibility with the actual OH-C-Chol structure and functional groups).

• Esterification/carbonate formation (at 3-OH):

  • Solvents: DCM, THF, pyridine or DMAP catalysis.
  • Reagents: Acyl chlorides/anhydrides or chloroformates; DMAP (5–20 mol%).
  • Temp: 0 °C to rt; times 1–16 h; typical yields 70–95% (literature).

• Carbamate linkage to amines (via 3-OH):

  • Using CDI or p-nitrophenyl chloroformate; DMF/DCM; base (Et3N).
  • Temp: 0 °C to rt; 2–12 h; yields 60–90%.

• Epoxidation of Δ5-alkene:

  • m-CPBA in DCM (0 °C to rt), 1–4 h; diastereoselective epoxides; 60–85%.

• Hydrogenation of Δ5-alkene:

  • H2, Pd/C (5–10%), EtOH/EtOAc, rt to 40 °C; 2–8 h; near-quantitative under optimized conditions.

• Click conjugation (if alkyne/azide present):

  • CuAAC: CuSO4/sodium ascorbate, t-BuOH/H2O or DMF, rt; 1–6 h; 70–95%.
  • SPAAC (strain-promoted): aqueous/organic mixtures, rt; slower kinetics; metal-free.

• Protection of 3-OH:

  • TBSCl/imidazole in DMF, rt to 50 °C; 2–6 h; 80–95%. Deprotect with TBAF in THF.

Notes:

• Dry, oxygen-minimized conditions help limit oxidation of unsaturated sites.
• Monitor reactions by TLC with neutral alumina or buffered silica to prevent acid-catalyzed rearrangements.
• Actual conditions must be tailored to the specific OH-C-Chol substituents—consult CoA/SDS.

Safety & Handling

Safety data specific to this item are not provided here. Always consult the product SDS for authoritative hazard classification and response procedures.

• GHS classification, Signal word, H-Statements, Pictograms: Not specified for this item; refer to SDS.

General sterol-derivative safety guidance (literature/practice):

• Hazards: Typically low volatility; dust from finely powdered solids may cause mechanical irritation. Hydrophobic organics can cause irritation on skin/eyes with prolonged contact. Avoid ingestion and inhalation of dust/aerosols.

• PPE: Lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood when weighing/dissolving in volatile organic solvents.

• Handling: Avoid dust generation. When dissolving in solvents (CHCl3, DCM, THF, methanol, DMSO), follow solvent-specific precautions (flammability, toxicity). Prevent static accumulation with organics.

• Incompatibilities: Strong oxidizers may react with unsaturated sterols; avoid strong acids/bases for prolonged periods unless intended for reaction. Store away from oxidants and sources of ignition.

• First aid (overview):

  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

• Waste: Collect solutions and contaminated disposables as organic chemical waste; follow institutional and local regulations.

• Storage per product data: Store at −20 °C. Shipments are sent cold (ice chest + ice pads). Minimize freeze–thaw by aliquoting.

Solvent Selection

This product is a hydrophobic, sterol-like small molecule; water solubility is expected to be poor. Item-specific solubility is not provided—verify on the CoA. The following is general guidance for cholesterol-type derivatives.

• Polarity/Miscibility: Highly nonpolar to amphiphilic depending on headgroup. Typically insoluble in water, miscible with many organic solvents.
• Common good solvents:
  • Chlorinated: chloroform, dichloromethane
  • Ethers/aprotic: THF, dioxane, MTBE (variable)
  • Aromatics: toluene
  • Polar aprotic: DMSO, DMF (often good for stock solutions)
  • Alcohols: ethanol, isopropanol (solubility varies with substitution)
• Poor solvents: Alkanes may dissolve slowly unless warmed; water generally unsuitable unless aided by surfactants or cyclodextrins.

Selection tips:

• For film hydration/liposome work: Use CHCl3/MeOH mixtures to co-dissolve components, evaporate, then hydrate.
• For biochemical assays: Prepare concentrated stocks in DMSO or ethanol, then dilute into buffer with vigorous mixing; keep final DMSO ≤1–2% v/v as assay permits.
• For synthetic transformations: Choose dry, anhydrous solvents compatible with planned reagents (e.g., DCM for acylations/carbonates; THF for organometallic steps).

Small comparison (general):

• DMSO: Excellent solvency; easy for stocks; may affect biological assays.
• Ethanol: Good compromise for many sterols; lower assay interference; limited solubility ceiling.
• Chloroform/DCM: Strong solvents for film prep and chromatography; handle with care due to toxicity/volatility.

Storage & Reconstitution

Item-specific storage conditions are provided; other details should be confirmed on the CoA.

• Storage (as provided): Store at −20 °C.
• Shipping: Ice chest + ice pads.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution solvent: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for cholesterol-type derivatives:

• Aliquoting: Upon receipt, allow to equilibrate to room temperature in a desiccator before opening to prevent condensation. Immediately re-seal under dry inert gas if possible.
• Stock solutions: Prepare concentrated stocks in anhydrous DMSO, ethanol, or chloroform depending on intended use. Record exact mass and volume for accurate concentration.
• Stability: Unsaturated sterols can be sensitive to oxidation; store solutions under inert gas (N2/Ar), protected from light, at −20 °C. Avoid repeated freeze–thaw cycles by making small aliquots.
• Solid storage: Keep tightly closed in a dry, inert atmosphere. Include desiccant. Avoid prolonged exposure to ambient light/heat.
• Working solutions: Use freshly prepared solutions for biological assays; discard if turbidity or precipitation occurs after dilution.

For any missing specification (e.g., exact solvent compatibility, shelf life, stabilizers), consult the product’s CoA or SDS. Research Use Note: For research use only.

Structure & Identity

Brief overview: OH-C-Chol appears to be a cholesterol-based small molecule (sterol-derived) supplied for research use. Item-specific identifiers are limited in the provided data; verify exact structure on the CoA/Spec Sheet.

• SKU: O1439878
• Product Name: OH-C-Chol
• CAS: 496801-51-5 (as provided)
• CID: 102032621 (as provided)
• InChIKey: 151543 (as provided; note: format atypical—confirm on CoA)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general, literature-level for cholesterol derivatives):

• Core scaffold: Tetracyclic cyclopentanoperhydrophenanthrene (sterol) nucleus with multiple stereocenters.
• Typical functionality: A secondary alcohol at C3 (often 3β-OH), an alkene at Δ5 (C5–C6), and an isooctyl-like aliphatic side chain at C17.
• 2D description (generic sterol): Three fused cyclohexane rings (A/B/C) and one fused cyclopentane ring (D), with angular methyls at C10 and C13 and a branched C17 side chain; one polar head group (OH) on ring A.

Important: The exact substitution pattern signified by “OH-C-” is not specified in the product data. Users should consult the specific CoA/SDS to confirm stereochemistry, substitution, and any special functional handles present in this item.

Synthetic Utility

Without a confirmed structure for OH-C-Chol, synthetic guidance is provided at the level of typical sterol chemistry (literature, not item-specific).

Key functional elements in sterol scaffolds:

• 3β-Hydroxyl group: Amenable to acylation (esters, carbonates), carbamate formation, silylation for protection, and activation (e.g., tosylation) to enable substitution.
• Δ5 double bond: Subject to epoxidation (m-CPBA), hydroboration–oxidation, halogenation, or oxidative cleavage; selectivity often controlled by sterics.
• Alkyl side chain: Oxidation at C20–C27 region or radical functionalization strategies can introduce handles.

Utility in synthesis:

• Membrane anchors: Conjugation via carbonate/ester/carbamate linkers to attach dyes, peptides, or PEG chains.
• Bioorthogonal handles: Installation of azide/alkyne groups (on side chain or at C3 via linkers) to facilitate click chemistry in membranes.
• Chiral pool: Multiple stereocenters allow derivation of complex stereodefined scaffolds for SAR studies.

Protecting-group strategy:

• Use TBS/TBDPS for the 3-OH when manipulating the ring system; remove under fluoride or acid as needed. For Δ5-sensitive routes, consider hydrogenation to cholestane followed by selective reoxidation if necessary.

Analytical:

• Characterize by 1H/13C NMR (diagnostic 3β-OH proton, olefinic signals), HRMS, and, if needed, 2D NMR to confirm substitution regiochemistry.

Target Specificity

This product is not an antibody or biologic, and no target-binding specificity is provided in the item data.

• No antigen/epitope, clone, isotype, or species reactivity is applicable.
• If the compound carries a known binding motif (e.g., for cholesterol-binding proteins), such information is not specified here and should be verified in the product CoA or associated technical notes.

Frequently Asked Questions

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 496801-51-5. InChIKey IVKGTZVIOSLOAM-PTHRTHQKSA-N.

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.