Campesterol - Moligand™, 10 mM in Ethanol , CAS No.474-62-4

CAS: 474-62-4 Cat. No.: C1499862 Formula: C₂₈H₄₈O Molecular Weight: 400.68 Beilstein Registry Number: 3216975 EC Number: 207-484-4

GRADE & PURITY Moligand™, 10 mM in Ethanol

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

Specifications

Specifications & Purity

Moligand™, 10 mM in Ethanol

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Grade

Moligand™

Names and Identifiers

Isomeric SMILES

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

WGK Germany

3

Molecular Weight

400.68

Beilstein

3216975

Reaxy-Rn

2061433

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2061433&ln=

Application Protocols

No application protocols are specified for this item; refer to CoA/Spec Sheet. This product is provided for research use only and has not been validated by the manufacturer for particular assay formats.

General guidance should be obtained from peer-reviewed literature and standard laboratory manuals for:

• Solubilization and delivery of hydrophobic sterols in biochemical assays.
• Derivatization workflows (e.g., silylation) for GC–MS analysis of sterols.

Note: The above are pointers only; no specific, validated protocols are provided by the manufacturer for this SKU.

Biological Roles

Biochemistry/literature overview (non-clinical):

• Campesterol is a major phytosterol in plants, structurally analogous to cholesterol but with a 24-methyl substituent in the side chain.
• Membrane function: Contributes to membrane order and permeability in plant cells; often studied alongside sitosterol and stigmasterol to probe phase behavior and lipid raft-like domains in model membranes.
• Biosynthesis: Derived from cycloartenol within the plant sterol pathway; serves as a metabolic intermediate toward brassinosteroids (plant steroid hormones) via hydroxylation/oxidation sequences in the C-22/C-23 region (literature).
• Metabolism in animals (research context): Absorption is limited compared to cholesterol; used as a dietary biomarker and internal standard in studies of sterol uptake and transport (non-clinical, analytical chemistry literature).
• Oxidative products: Like other Δ5-sterols, campesterol can form oxysterol derivatives under oxidative stress; these are relevant to lipid oxidation studies in food and biological systems (analytical focus).

Notes:

• The above describes general, literature-based biological roles and analytical contexts. No medical or clinical claims are made. For experimental design, consider solubilization strategies (e.g., cyclodextrins, liposomes, or low-% DMSO/cosolvent) to deliver this hydrophobic sterol to aqueous systems.

Buffer Applications

Campesterol is a highly hydrophobic neutral sterol and is not used as a buffering agent. It does not form conventional aqueous buffer systems.

• Practical note: For studies requiring campesterol in aqueous media (e.g., biophysical assays), incorporate it via carriers rather than buffers:
  • Cosolvent delivery (e.g., ≤1–2% v/v DMSO or ethanol final concentration).
  • Lipid vehicles (liposomes with phospholipids), cyclodextrin inclusion complexes, or protein carriers (e.g., BSA) prepared in the chosen buffer.

For pH control, employ standard buffer systems appropriate to the assay (e.g., phosphate, HEPES, Tris) independently of campesterol.

Green Alternatives

Greener handling of campesterol focuses on solvent choice and milder reagents for common derivatizations.

• Solvent substitutions (literature/general):
  • Replace chlorinated solvents (CHCl3, DCM) with ethyl acetate, 2-MeTHF, CPME, or heptane/IPA mixtures when feasible.
  • Use ethanol or isopropanol for preparing assay stocks instead of more hazardous solvents, provided downstream systems tolerate the cosolvent.
• Reagent choices for common transformations:
  • Acylation: Employ acyl anhydrides with catalytic DMAP in green solvents (EtOAc or 2-MeTHF) rather than acid chlorides in DCM/pyridine.
  • Oxidation: Prefer Dess–Martin periodinane under controlled conditions or catalytic TEMPO/bleach systems in biphasic media over chromium(VI) reagents; manage work-up to minimize waste.
  • Silylation for GC–MS is often necessary; minimize excess silylating reagent and quench/neutralize responsibly.
• Energy and waste:
  • Exploit room-temperature or microwave-accelerated reactions to reduce time/energy.
  • Consider enzymatic esterification (lipases) in solvent-free or green solvent systems for selective 3β-OH modification.

Example comparison (general):

• Traditional: Acylation in DCM/pyridine, stoichiometric reagents, chlorinated waste.
• Greener: Ac2O (1.1–1.5 eq) + catalytic DMAP in EtOAc or 2-MeTHF at rt–40 °C; simpler work-up and reduced toxicity.

Trade-offs:

• Solubility may be lower in some green solvents; mild heating or co-solvent strategies can compensate. Always validate target assay compatibility.

Pharmaceutical Uses

Research/formulation context (non-clinical):

• Excipient analog: In pre-formulation and delivery research, campesterol can serve as a sterol component analogous to cholesterol to modulate membrane rigidity, bilayer packing, and permeability in liposomal or lipid nanoparticle model systems (literature/general). Its use is exploratory and assay-dependent.
• Reference standard: Utilized as an analytical reference in QC-method development for phytosterol-containing excipient blends and nutritional matrices.
• Compatibility considerations:
  • Solubility: Insoluble in water; dissolve in ethanol, isopropanol, DMSO, or chlorinated solvents before incorporation into lipid phases.
  • Processing: Can be co-dissolved with phospholipids in volatile solvents and film-cast prior to hydration to make sterol-containing vesicles (general formulation practice).
  • Stability: Protect from light, oxygen, and heat to minimize autoxidation of the Δ5 double bond.

No therapeutic or clinical claims are made. Confirm regulatory status and pharmacopeial requirements if using campesterol in any regulated development; this product is designated for research use only.

Physical Properties

• Physical state/appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Typically ~157–159 °C (literature, crystalline solid; reported ranges vary slightly with purity and polymorph).
• Boiling point: Not commonly reported; thermal decomposition occurs before distillation under ambient pressure (literature).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature):
  • Water: Practically insoluble.
  • Organic solvents: Soluble in chloroform, dichloromethane, and hot ethanol or isopropanol; soluble in ethers and hexanes to varying degrees; dissolves in DMSO upon gentle warming and sonication.
• LogP: High hydrophobicity expected for a C28 sterol; reported cLogP values are typically >7 (literature, method-dependent).
• pKa: Not applicable for the neutral secondary alcohol under aqueous conditions; the 3β-OH does not ionize appreciably in water (literature/general).
• UV/Vis: No strong chromophores; weak end absorption only (literature). For HPLC-UV detection, low-wavelength detection (e.g., 205–210 nm) or derivatization is often used (literature/practice).
• Refractive index: Not applicable to a solid; Not specified for this item.

Notes:

• Values above are literature/general properties for campesterol and are not item-specific specifications. Actual analytical specifications (e.g., polymorph, solvent content) are Not specified for this item; refer to CoA/Spec Sheet.

Quality & Grades

• Item grade: Moligand™ (from Product Data).
• Interpretation:
  • Moligand™ denotes inclusion in a curated small-molecule/compound library suitable for screening, ligand discovery, or chemical biology research. It emphasizes traceability, catalog consistency, and suitability for research workflows rather than analytical chromatography specifications.
• What this implies for users:
  • Material is intended for research use only (as stated). It is appropriate for biochemical assays, screening, and synthetic use where a well-characterized phytosterol standard is required.
  • UV cutoff, residual solvent limits, metal content, water content, and stabilizers are Not specified for this item; refer to CoA/Spec Sheet if these parameters are critical.
• Comparison to other common grades (general guidance):
  • Reagent/technical grade: adequate for many synthetic applications but may vary in assay and impurity profile.
  • Analytical reference grade: typically includes certified purity and identity suitable for quantitative calibration; if a reference standard is required, verify via the CoA.
  • HPLC grade (solvents) is not applicable here; for sterol solids, low-UV background is generally irrelevant, but impurity profile and isomeric purity can matter for bioassays.
• Stabilizers/antioxidants:
  • None specified for this item. If long-term storage is planned, users sometimes add inert-atmosphere protection or store as solutions under nitrogen to minimize slow oxidation (general practice; not item-specific).

Reaction & Applications

As a 5-ene sterol with a single secondary alcohol (3β-OH), campesterol participates in characteristic steroid transformations and serves as a useful analytical standard.

• Synthetic/derivatization applications (literature/general):
  • Esterification/acylation at 3β-OH: Ac2O or acyl chloride with base (or catalytic DMAP) affords steryl esters—relevant for lipid chemistry and solubility modulation.
  • Silylation for GC–MS: TMS or TBDMS ethers (e.g., BSTFA, MSTFA) increase volatility and thermal stability for gas-phase analysis.
  • Oxidation to 3-ketosteroids: PCC/PDC, Dess–Martin, or Jones (controlled) convert 3β-OH to a 3-one; subsequent Δ5→Δ4 isomerization and 1,2-shifts follow classic steroid chemistry.
  • Hydrogenation: Catalytic hydrogenation (e.g., Pd/C, H2) saturates the Δ5 double bond to give the corresponding stanol (campestanol).
  • Epoxidation/ozonolysis: The Δ5 alkene can undergo peracid epoxidation or oxidative cleavage under stronger conditions.
• Research uses (literature/general):
  • Phytosterol reference material for plant lipidomics and quantitation in food/feed matrices.
  • Model sterol in membrane biophysics (phase behavior, raft formation) alongside cholesterol and β-sitosterol.
  • Precursor/scaffold in brassinosteroid-related synthesis and sterol metabolism studies.
• Practical notes:
  • Control stereochemistry at C3 during protection/deprotection to maintain β-configuration.
  • For analytical workflows, include internal standards and, if using GC–MS, implement saponification and derivatization steps to liberate/convert steryl esters.
  • Dry, oxygen-limited conditions reduce slow autoxidation and preserves Δ5-ene integrity.

Reaction Conditions

General, literature-based conditions commonly applied to campesterol and related Δ5-sterols (guide values; optimize per laboratory conditions):

• Esterification (3β-OH):
  • Reagents: Ac2O (1.1–1.5 eq) + catalytic DMAP (5–10 mol%) or acyl chloride (1.1 eq) + Et3N.
  • Solvents: DCM, EtOAc, or 2-MeTHF.
  • Temperature/time: 20–40 °C, 1–6 h.
  • Work-up: Aqueous quench, wash, silica purification.
• Silylation (GC–MS derivatization):
  • Reagents: BSTFA or MSTFA (with 1% TMCS if needed).
  • Solvent: Anhydrous acetonitrile or pyridine.
  • Conditions: 60–70 °C, 20–60 min; cool, inject.
• Oxidation to 3-ketone:
  • PCC (1.5 eq) in DCM at 0–25 °C, 1–3 h; or Dess–Martin periodinane (1.3 eq) in DCM at 0–25 °C, 0.5–2 h.
  • Notes: Monitor to limit over-oxidation and Δ5→Δ4 isomerization unless desired.
• Hydrogenation of Δ5-alkene:
  • Catalyst: 5–10 wt% Pd/C (5–10 mol% Pd rel.).
  • Solvent: EtOAc, ethanol, or ethyl acetate/EtOH.
  • Conditions: H2 (1–3 atm), 20–25 °C, 1–6 h; filter over celite.
• Epoxidation:
  • Reagent: mCPBA (1.1 eq) in DCM at 0–5 °C to rt, 1–3 h; wash with Na2SO3/NaHCO3.

Expected isolated yields for these transformations are often 70–95% under optimized conditions (literature). Always confirm identity/purity by NMR (noting characteristic 3β-H and Δ5 signals), MS, and, if needed, chiral/stereochemical assays.

Safety & Handling

• GHS classification, signal word, pictograms, and hazard statements: Not specified for this item; refer to the SDS for authoritative safety information.
• General hazards (literature/practice for sterol solids):
  • Low acute toxicity expected; may cause mechanical irritation to eyes, skin, or respiratory tract as dust.
  • Combustible organic solid; avoid dust formation and ignition sources.
• Recommended PPE and hygiene:
  • Wear lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Handle in a fume hood when weighing or dissolving to minimize dust and solvent exposure.
  • Avoid inhalation of dust; use local exhaust or handle in a glovebox/hood if finely powdered.
• Incompatibilities (general):
  • Strong oxidizers (can oxidize the 3β-alcohol and the Δ5 double bond).
  • Strong acids/bases under forcing conditions may cause dehydration/isomerization.
• First-aid overview (general, defer to SDS):
  • Inhalation: Move to fresh air. Seek medical attention if symptoms persist.
  • Skin contact: Wash with soap and water. Remove contaminated clothing.
  • Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice if unwell.
• Fire-fighting (general):
  • Use CO2, dry chemical, or foam. Fine dust can be explosible; avoid creating dust clouds.

Always consult the product-specific SDS and institutional safety procedures before use.

Solvent Selection

Campesterol is a highly hydrophobic sterol. Selecting an appropriate solvent is crucial for accurate dosing and assay performance.

• Polarity profile (literature/general):
  • Nonpolar to weakly polar neutral alcohol; miscible with many nonpolar and moderately polar organic solvents.
• Recommended solvents and use cases:
  • Chloroform or dichloromethane: Rapid dissolution at room temperature; useful for preparative work and TLC. Note environmental/health considerations.
  • Ethyl acetate, toluene, or hexanes: Suitable for chromatography and recrystallization; solubility moderate in hexanes, higher in ethyl acetate.
  • Alcohols (ethanol, isopropanol): Solubility improves on heating; common for preparing stock solutions for biochemical use when aqueous compatibility is needed after cosolvent dilution.
  • DMSO: Forms concentrated stock solutions with gentle warming and sonication; compatible with many screening assays at low final % DMSO.
  • THF, tert-butyl methyl ether (TBME), 2-MeTHF, CPME: Good solubility; consider peroxide formation risks for ethers (general solvent safety).
• Aqueous systems:
  • Insoluble in water; for biological assays, deliver via cosolvent (e.g., DMSO ≤1–2% v/v final) or use cyclodextrin/lipid carriers (general practice).
• Practical tips:
  • Warm and sonicate viscous or saturated solutions; filter through PTFE if particulates remain.
  • For quantitative dosing, prepare a concentrated anhydrous stock (e.g., 10–50 mM in DMSO or ethanol) and store aliquots at low temperature under inert gas (general practice).

Storage & Reconstitution

• Storage conditions (from Product Data): Store at -80 °C.
• Shipping (from Product Data): Shipped on dry ice packs + cold packs.
• Container and atmosphere (general good practice):
  • Keep tightly sealed in an inert container under dry, inert gas (e.g., nitrogen or argon) to minimize moisture and oxygen exposure.
  • Protect from light to reduce photo-oxidation of the Δ5 double bond.
• Reconstitution/dissolution (general guidance; not item-specific):
  • To prepare stock solutions, dissolve in anhydrous solvents such as DMSO, ethanol, isopropanol, chloroform, or dichloromethane. Gentle warming (30–40 °C) and sonication can aid dissolution.
  • For aqueous applications, deliver via low-percentage cosolvent or incorporate into lipid carriers (e.g., film hydration with phospholipids to form liposomes).
  • Filter through PTFE (0.2–0.45 µm) if particulate matter is present.
• Aliquoting:
  • Prepare single-use aliquots of solid or concentrated stock solutions to avoid repeated freeze–thaw cycles. Store aliquots at -80 °C per Product Data.
• Stability monitoring:
  • Inspect periodically by TLC or HPLC for signs of oxidation (new polar spots/peaks). If degradation is observed, prepare fresh solutions and enhance oxygen exclusion.

All handling should follow institutional SOPs. For definitive shelf-life and retest information, refer to the item’s CoA/Spec Sheet.

Structure & Identity

Campesterol is a plant-derived sterol (phytosterol) structurally related to cholesterol, featuring the steroid tetracyclic core and a 3β-hydroxyl group.

• Item-specific registry identifiers:
  • CAS: 474-62-4 (from Product Data)
  • SKU: C1499862 (Aladdin Scientific)
• Structure identifiers:
  • Molecular formula: C28H48O (literature)
  • Molecular weight: ~400.68 g/mol (literature)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Stereochemistry and ring system (literature/general description):
  • Core: Perhydrocyclopenta[a]phenanthrene (steroid nucleus: fused A/B/C/D rings)
  • Functional groups: One secondary alcohol at C3 (3β-OH); one C=C double bond typically at Δ5 (between C5–C6) in the B-ring; saturated side chain bearing a 24-methyl substituent (i.e., 24-methylcholesterol).
  • Chiral centers: Multiple defined stereocenters at the steroid framework (including C3 β-configuration), consistent with natural 5-ene sterol topology.
• 2D structure in words (literature/general):
  • Four fused rings (three six-membered and one five-membered) with a single endocyclic double bond in ring B; a β-oriented hydroxyl at C3 on ring A; an aliphatic side chain at C17 extending from ring D that contains a methyl substituent at C24 (total side chain length analogous to cholesterol but 24-methyl substituted).

Synthetic Utility

Campesterol provides a chiral, polyfunctional steroid framework valuable in synthesis and method development.

• Functional group handles (literature/general):
  • 3β-Hydroxyl: amenable to protection (silyl/benzyl/acetyl), oxidation to ketone, or activation for glycosylation/esterification.
  • Δ5-Alkene: platform for epoxidation, hydroboration–oxidation, halogenation, or hydrogenation to the corresponding stanol.
  • Side chain (C17–C24 methylated): can undergo oxidative cleavage or chain extension/modification for analog generation.
• Chiral pool advantages:
  • Pre-installed stereochemistry across the steroid nucleus reduces the need for de novo asymmetric induction when targeting steroidal frameworks or brassinosteroid-like molecules.
• Applications:
  • Preparation of steryl esters and ethers as lipid probes.
  • Synthesis of 3-keto-Δ4 derivatives and further elaboration via Robinson annulation analogs and Wagner–Meerwein rearrangements typical of steroid chemistry.
  • Late-stage diversification via C–H oxidation strategies at allylic positions.
• Analytical utility:
  • Serves as a standard for validating saponification/derivatization workflows in GC–MS and LC–MS lipidomics.

Practical considerations:

• Maintain anhydrous, oxygen-reduced conditions during transformations to limit side oxidation.
• Control of Δ5↔Δ4 isomerization during oxidation is key to product selectivity in steroid series.

Target Specificity

Not applicable. This product is a small-molecule phytosterol, not an antibody or targeted biological reagent. No antigen/epitope or species reactivity applies. For biochemical interactions of sterols with proteins or membranes, refer to the scientific literature rather than product-specific target data.