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| Targets |
The primary target of Cholesterol beta-D-glucoside is heat shock transcription factor 1 (HSF1), which it activates under heat shock conditions. By activating HSF1, the compound induces the expression of heat shock proteins (HSPs), particularly Hsp70. This cytoprotective response helps cells withstand various stresses including heat, oxidative stress, and inflammation. Cholesterol beta-D-glucoside also exhibits anti-ulcer effects via its HSF1-activating properties.
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| ln Vitro |
Cholesterol beta-D-glucoside activates heat shock transcription factor 1 (HSF1) and increases Hsp70 expression and protein levels. In TIG-3 human fetal lung fibroblasts, it increases the expression of heat shock protein 70 (Hsp70) when used at a concentration of 10 uM. It also increases Hsf1 activity in rat gastric mucosa. As a lipid mediator in heat stress responses in animals, it shows anti-ulcer effects.
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| ln Vivo |
Cholesterol beta-D-glucoside (100 mg/kg) prevents ulcer formation following cold-restraint stress and increases Hsf1 activity, as well as Hsp70 expression and protein levels in rat gastric mucosa. This demonstrates its in vivo efficacy as a gastroprotective agent in an animal model of stress-induced ulcer formation. The compound is formed from cholesterol and glucosylceramide by beta-glucosidase 1.
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| Enzyme Assay |
Not applicable. Cholesterol beta-D-glucoside is a natural lipid mediator, not a compound typically used in non-cellular enzyme binding assays. A typical protocol for studying HSF1 activation: Cells are treated with compound for 1-2 hours, nuclei are extracted, and HSF1 binding to DNA is measured by electrophoretic mobility shift assay (EMSA) using an HSE (heat shock element) probe. Alternatively, Hsp70 promoter-driven luciferase reporter assays are used to quantify transactivation.
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| Cell Assay |
Standard cell-based assay for heat shock protein induction: TIG-3 human fetal lung fibroblasts or other cell lines are seeded in 6-well plates. Cells are treated with Cholesterol beta-D-glucoside at concentrations of 1, 10, and 50 uM for 2-4 hours at 37degC. For positive control, cells are heat-shocked at 42degC for 30 minutes. After treatment, cells are lysed, and Hsp70 protein levels are measured by Western blot. Hsp70 mRNA is quantified by qPCR. HSF1 activation can also be detected by immunofluorescence showing nuclear translocation.
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| Animal Protocol |
Rat cold-restraint stress model: Male Sprague-Dawley rats (200-250 g) are fasted for 24 hours. Cholesterol beta-D-glucoside is administered orally at 100 mg/kg 30 minutes before stress. Rats are then restrained in a cold environment (4degC) for 2-4 hours. At the end of the stress period, rats are euthanized, and stomachs are removed. Gastric mucosal lesions (ulcers) are scored visually. Stomach tissue is collected for Hsf1 activity and Hsp70 expression analysis.
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| ADME/Pharmacokinetics |
No specific PK data was found for Cholesterol beta-D-glucoside. As a natural steroid glycoside, it is expected to have moderate oral bioavailability. After absorption, it is likely distributed to various tissues, particularly the gastrointestinal tract. Metabolism may involve hydrolysis of the glucose moiety by beta-glucosidases, releasing free cholesterol. The compound may also be excreted in bile as glucuronidated metabolites.
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| Toxicity/Toxicokinetics |
Cholesterol beta-D-glucoside is a naturally occurring steryl glycoside with a generally favorable safety profile. At 100 mg/kg in rats, it prevents ulcer formation without apparent toxicity in acute dosing. No specific long-term toxicity or genotoxicity data is available, but as an endogenous compound, it is considered to have low toxicity. For research use only, not for human consumption.
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| References | |
| Additional Infomation |
Cholesteryl beta-D-glucoside is a sterol 3-β-D-glucoside and a monosaccharide derivative. Functionally, it is associated with cholesterol. Cholesteryl beta-D-glucoside has been reported to exist in Salvia deserti, Euglena gracilis, and Salvia deserta, and relevant data are available.
Cholesterol beta-D-glucoside (Cholesteryl beta-D-glucopyranoside) has molecular formula C33H56O6 and molecular weight 548.80. Purity ≥97% by TLC. It is a naturally occurring steryl glycoside and lipid mediator that activates HSF1, induces Hsp70 expression, and shows anti-ulcer effects in animal models. Soluble in ethanol (20 mg/ml). Store at -20degC. For research use only, not for human therapeutic applications. |
| Molecular Formula |
C33H56O6
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|---|---|
| Molecular Weight |
548.79
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| Exact Mass |
548.408
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| CAS # |
7073-61-2
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| PubChem CID |
440145
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| Appearance |
Typically exists as solids at room temperature
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| LogP |
5.213
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
39
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| Complexity |
874
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| Defined Atom Stereocenter Count |
13
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| SMILES |
O(C1CCC2(C)C(=CCC3C2CCC2(C)C3CCC2C(C)CCCC(C)C)C1)C1OC(CO)C(O)C(O)C1O
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| InChi Key |
FSMCJUNYLQOAIM-UQBZCTSOSA-N
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| InChi Code |
InChI=1S/C33H56O6/c1-19(2)7-6-8-20(3)24-11-12-25-23-10-9-21-17-22(13-15-32(21,4)26(23)14-16-33(24,25)5)38-31-30(37)29(36)28(35)27(18-34)39-31/h9,19-20,22-31,34-37H,6-8,10-18H2,1-5H3/t20-,22+,23+,24-,25+,26+,27-,28-,29+,30-,31-,32+,33-/m1/s1
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| Chemical Name |
(2R,3R,4S,5S,6R)-2-[[(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]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
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| Synonyms |
Cholesteryl glucoside
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| HS Tariff Code |
2934.99.9001
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| 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)
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| 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
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| 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 | 1.8222 mL | 9.1110 mL | 18.2219 mL | |
| 5 mM | 0.3644 mL | 1.8222 mL | 3.6444 mL | |
| 10 mM | 0.1822 mL | 0.9111 mL | 1.8222 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.
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