| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
|
||
| 100mg |
|
||
| Other Sizes |
Purity: ≥98%
| Targets |
5α-Cholestane itself does not have a defined direct pharmacological target. However, its derivatives (such as oxysterols bearing hydroxyl or keto groups) can influence key enzymes involved in cholesterol metabolism. For instance, studies have shown that amino analogs of 5α-cholestane-3β,5α,6β-triol can modulate enzymes responsible for cholesterol biosynthesis, with some derivatives exhibiting inhibitory activity and others showing activating effects. At the systemic metabolic level, the 5α-cholestane skeleton can be catalyzed and hydroxylated (e.g., 12α-hydroxylation) by cytochrome P450 enzymes in liver microsomes to form bile acids.
5α-Cholestane does not have a specific pharmacological target. It is a sterol produced endogenously from cholesterol and has been isolated from human feces. It is used as an internal standard for the quantification of phytosterols by HPLC-MS/MS and fecal sterols by GC-FID and GC-MS. |
|---|---|
| ln Vitro |
In standard cell-free or cellular systems, 5α-Cholestane (CAS: 481-21-0) itself is generally not considered to possess direct biological activity. Its scientific value lies primarily in its use as an analytical standard or a model compound for biochemical research. Studies regarding biological activity usually focus on its structural derivatives, such as polyhydroxylated sterol esters isolated from starfish containing the 5α-cholestane skeleton. These derivatives have demonstrated in vitro antiviral activity (with MIC values as low as 0.05 µM against Herpes Simplex Virus type 1, HSV-1) and cytotoxicity against human liver carcinoma HepG2 cells.
In vitro activity data for 5α-Cholestane are not applicable, as it is a chemical standard rather than a biologically active compound. Its primary use is as an analytical reference standard for sterol quantification. |
| ln Vivo |
The in vivo activity of 5α-Cholestane is primarily exemplified by its role as a metabolic intermediate. Studies have shown that after intraperitoneal injection of labeled 5α-cholestane-3β,7α-diol into rats, the compound is efficiently converted into bile acids (such as allochenodeoxycholic acid and allocholic acid) and excreted in the bile. This confirms that the 5α-cholestane skeleton can be recognized by metabolic enzymes and converted into physiologically functional bile acid molecules involved in lipid digestion and absorption. Furthermore, in vitro experiments using rabbit liver microsomes have also demonstrated that 5α-cholestane sterols can serve as substrates for 12α-hydroxylation reactions.
In vivo activity data for 5α-Cholestane are not applicable, as it is a chemical standard rather than a therapeutic agent. It is a sterol found in dust samples from various environments and is produced endogenously from cholesterol. |
| Enzyme Assay |
Although 5α-Cholestane itself is not commonly used in binding assays, cell-free enzymatic assays for its hydroxylation metabolism are standard. The typical procedure utilizes a liver microsome system: Microsomes (rich in CYP450 enzymes) are prepared from rat or rabbit livers via differential centrifugation. The microsomes are incubated with the substrate (e.g., 5α-cholestane-3α,7α-diol) in the presence of 0.1 mM NADPH at 37°C for 60 minutes. The reaction is terminated by organic solvent extraction, and the hydroxylated products (e.g., 12α-hydroxy derivatives) are separated and quantified using Thin-Layer Chromatography (TLC) or High-Performance Liquid Chromatography (HPLC).
The non-cellular assay for 5α-Cholestane involves its use as an analytical standard. Key analytical techniques include HPLC-MS/MS for phytosterol quantification and GC-FID and GC-MS for fecal sterol quantification. Its chemical properties are confirmed by NMR, HPLC, and GC. |
| Cell Assay |
5α-Cholestane itself, serving as a sterol nucleus, is often used as a negative control or as a basic model to assess cellular uptake and metabolism. In cellular assays, it is dissolved in an organic solvent (such as DMSO or ethanol) and then diluted with culture medium to working concentrations (typically in the low µM range) to treat cells (e.g., hepatocytes HepG2, neuronal cells SK-N-BE). The general procedure involves: seeding cells for overnight attachment, followed by treatment with the compound-containing medium for 24-72 hours. Detection endpoints may include: assessment of cytotoxicity via MTT assay, measurement of Reactive Oxygen Species (ROS) levels using fluorescent probes, or analysis of expression changes of related metabolic enzymes or receptors via qPCR/Western Blot. For instance, 6α-hydroxy-5α-cholestane has been shown to promote superoxide anion production in neuronal cells.
In vitro cell-based assays are not applicable for 5α-Cholestane, as it is an analytical standard rather than a biologically active compound. |
| Animal Protocol |
In vivo experiments involving 5α-Cholestane-related compounds are primarily used to study steroid metabolic kinetics and transformation pathways. A classic protocol uses the bile duct-cannulated rat model: Adult male rats receive an intraperitoneal injection of a labeled 5α-cholestane-3β,7α-diol (approximately 0.9 mg, dual-labeled with 14C and 3H). Bile is continuously collected for up to 11 days post-injection. The absorption and excretion of the drug are tracked by measuring radioactivity in the bile. Subsequently, bile acids are separated via chromatography, and metabolite structures are determined using isotope ratio analysis, typically finding the majority of radioactivity concentrated in allochenodeoxycholic and allocholic acids.
In vivo animal study protocols are not applicable for 5α-Cholestane, as it is not a therapeutic agent. |
| ADME/Pharmacokinetics |
Systemic pharmacokinetic data for 5α-Cholestane itself is very limited, as it is primarily a research tool rather than a drug candidate. However, studies on its metabolites (bile acids) indicate that these molecules primarily undergo enterohepatic circulation. From a physicochemical perspective, 5α-Cholestane (Molecular Formula: C27H48, Molecular Weight: 372.7) is a highly hydrophobic molecule. Available data indicates its melting point is approximately 80-82°C, and as a standard, it is typically stored dissolved in chloroform (10 mg/mL). In studies using secondary deuterated forms (5α-Cholestane-d6), stable isotope labeling is primarily used for quantitative tracking, suggesting that the concentration of the parent compound in vivo might be low, requiring sensitive detection methods.
Pharmacokinetic properties of 5α-Cholestane are not characterized, as it is not a therapeutic agent. It is a saturated hydrocarbon with a molecular weight of 372.67. It is used as an analytical standard. |
| Toxicity/Toxicokinetics |
According to the Material Safety Data Sheet (MSDS), 5α-Cholestane is classified as a Harmful substance (Xn). Specific risk codes include: R22 (Harmful if swallowed), R38 (Irritating to skin), R40 (Limited evidence of a carcinogenic effect), and R48/20/22 (Danger of serious damage to health by prolonged exposure). The UN number is 1888, packing group III, and it belongs to Class 6.1 (Toxic substances). Although its core structure exists in natural organisms, high concentrations of the pure chemical reagent pose certain health risks, necessitating the use of appropriate personal protective equipment and handling in a fume hood.
Toxicological data for 5α-Cholestane are limited. As a naturally occurring sterol, it is generally considered safe. Standard safety precautions should be observed during handling. |
| References |
[1]. https://pubchem.ncbi.nlm.nih.gov/compound/2723895
|
| Additional Infomation |
Structural Features: 5α-Cholestane is the 5α-stereoisomer of cholestane, characterized by a trans configuration of the A/B ring (5α-H), making its molecular skeleton more planar compared to its 5β-isomer (coprostane).Sources: Besides chemical synthesis, 5α-cholestane has been reported in natural sources, such as the plant Ornithogalum thyrsoides and the starfish Luidia maculata.Derivative Activity: Although the core structure lacks pharmacodynamic activity, its hydroxylated derivatives exhibit significant bioactivity. For instance, the isolate (25S)-5α-cholestane-3β,6α,7α,8,15α,16β-hexahydroxyl-26-O-14'Z-eicosenoate from starfish shows potent inhibitory activity against HSV-1 virus (MIC 0.05 μM).Chromatographic Applications: Due to its stable chemical properties and defined retention time, 5α-Cholestane is often used as an internal standard in Gas Chromatography-Mass Spectrometry (GC-MS) analysis for quantifying sterols in environmental or biological samples.Melting Point and Thermodynamics: The NIST database records thermodynamic data for hydrogenation reactions involving 5α-Cholestane, with enthalpy changes (ΔrH°) for hydrogenation reactions ranging approximately from -108 to -117 kJ/mol.
5α-Cholestane (α-cholestane) is a naturally occurring triterpene and sterol precursor. It is used as an internal standard for sterol quantification by HPLC-MS/MS, GC-FID, and GC-MS. It is not a therapeutic drug and has no clinical trial or marketing authorization status. |
| Molecular Formula |
C27H48
|
|---|---|
| Molecular Weight |
372.67
|
| Exact Mass |
372.376
|
| CAS # |
481-21-0
|
| PubChem CID |
2723895
|
| Appearance |
White to off-white solid powder
|
| Density |
0.9±0.1 g/cm3
|
| Boiling Point |
440.9±12.0 °C at 760 mmHg
|
| Melting Point |
80 - 80.5 °C
|
| Flash Point |
210.3±13.1 °C
|
| Vapour Pressure |
0.0±0.5 mmHg at 25°C
|
| Index of Refraction |
1.492
|
| LogP |
12.26
|
| Hydrogen Bond Donor Count |
0
|
| Rotatable Bond Count |
5
|
| Heavy Atom Count |
27
|
| Complexity |
506
|
| Defined Atom Stereocenter Count |
8
|
| SMILES |
[C@]12(C([H])([H])[H])C([H])([H])C([H])([H])[C@]3([H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]4([H])C([H])([H])C([H])([H])[C@@]3([H])[C@]1([H])C([H])([H])C([H])([H])[C@]2([H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]
|
| InChi Key |
XIIAYQZJNBULGD-XWLABEFZSA-N
|
| InChi Code |
InChI=1S/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21-,22+,23-,24+,25+,26+,27-/m1/s1
|
| Chemical Name |
(5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
|
| Synonyms |
5-alpha-Cholestane; 5alpha-Cholestane; 481-21-0; alpha-Cholestane; (5alpha)-Cholestane; 5-alpha-Cholestane;
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6833 mL | 13.4167 mL | 26.8334 mL | |
| 5 mM | 0.5367 mL | 2.6833 mL | 5.3667 mL | |
| 10 mM | 0.2683 mL | 1.3417 mL | 2.6833 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
COA