-Epoxycholesterol Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C27H44O2 |
| Molecular Weight | 400.64 |
| Exact Mass | 400.334 |
| CAS # | 77058-74-3 |
| PubChem CID | 3247059 |
| Appearance | White to off-white solid powder |
| Density | 1.05 |
| Boiling Point | 496.4ºC at 760 mmHg |
| Flash Point | 201.2ºC |
| Index of Refraction | 1.544 |
| LogP | 6.52 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 29 |
| Complexity | 680 |
| Defined Atom Stereocenter Count | 9 |
| SMILES | C[C@H](CC[C@H]1C(O1)(C)C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O)C)C |
| InChi Key | OSENKJZWYQXHBN-XVYZBDJZSA-N |
| InChi Code | InChI=1S/C27H44O2/c1-17(6-11-24-25(2,3)29-24)21-9-10-22-20-8-7-18-16-19(28)12-14-26(18,4)23(20)13-15-27(21,22)5/h7,17,19-24,28H,6,8-16H2,1-5H3/t17-,19+,20+,21-,22+,23+,24+,26+,27-/m1/s1 |
| Chemical Name | (3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-[(2S)-3,3-dimethyloxiran-2-yl]butan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol |
| 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) |
Biological Activity
| ln Vitro | 24S,25-Epoxycholesterol (1-10 μM) upregulates LXR-related genes ABCA1, ABCG1, and APOE, promotes cholesterol efflux, thereby preventing foam cell formation, and blocks the proliferation of mouse and human glioma stem cells by eliminating cellular cholesterol[1][3]. 24S,25-Epoxycholesterol inhibits the proliferation and migration of HGC27, which is enhanced by knockout of LXRβ[2]. 24S,25-Epoxycholesterol (40 μM) inhibits HMG-CoA reductase and activates LXR, thereby inhibiting mevalonate-dependent isoprenoid production and enhancing ATP-binding cassette transporter G1 expression, inducing apoptosis of bone marrow-derived mouse mast cells (BMMC)[5]. |
| ln Vivo | 24S,25-Epoxycholesterol (5 mM, intracerebroventricular injection) can enhance neurogenesis and limit neurodegeneration in midbrain dopamine neurons (mDA) in CYP46A1-overexpressing mice [4]. |
| Cell Assay |
Cell Proliferation Assay[2] Cell Types: HGC27 Concentration: 1 μM Incubation Duration: 18 h Experimental Results: Inhibited proliferation of HGC27 Cell Migration Assay [2] Cell Types: HGC27 Concentration: 1 μM Incubation Duration: 18 h Experimental Results: Reduced HGC27 migration. |
| Animal Protocol |
Animal/Disease Models:GGPP induced mDA neurogenesis defect in CYP46A1 overexpressing CD-1 mice[4] Doses: 5 mM Route of Administration: icv, 1 μL, single dosage Experimental Results: Increased levels of mDA neurons, blocked the GGPP induced decrease of double EdU and TH cells. |
| References |
[1]. Selective up-regulation of LXR-regulated genes ABCA1, ABCG1, and APOE in macrophages through increased endogenous synthesis of 24(S),25-epoxycholesterol. J Biol Chem. 2007 Feb 23;282(8):5207-16. [2]. , Upregulation of 24(R/S),25-epoxycholesterol and 27-hydroxycholesterol suppresses the proliferation and migration of gastric cancer cells. Biochem Biophys Res Commun. 2018 Oct 12;504(4):892-898. [3]. , Selective and brain-penetrant lanosterol synthase inhibitors target glioma stem-like cells by inducing 24(S),25-epoxycholesterol production. Cell Chem Biol. 2023 Feb 16;30(2):214-229.e18. [4]. , 24(S),25-Epoxycholesterol and cholesterol 24S-hydroxylase (CYP46A1) overexpression promote midbrain dopaminergic neurogenesis in vivo. J Biol Chem. 2019 Mar 15;294(11):4169-4176. [5]. , Mast cell death induced by 24(S),25-epoxycholesterol. Exp Cell Res. 2010 Nov 15;316(19):3272-81. |
| Additional Infomation | 24(S),25-epoxycholesterol is a 3beta-hydroxy-Delta(5)-steroid that is desmosterol in which the double bond at position 24-25 has been oxidised to the corresponding epoxide (the 24S diastereoisomer). It is an oxysterol agonist of the liver X receptor. It has a role as a liver X receptor agonist. It is a cholestanoid, a 3beta-hydroxy-Delta(5)-steroid and an epoxy steroid. It is functionally related to a desmosterol. |
Solubility Data
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4960 mL | 12.4800 mL | 24.9601 mL | |
| 5 mM | 0.4992 mL | 2.4960 mL | 4.9920 mL | |
| 10 mM | 0.2496 mL | 1.2480 mL | 2.4960 mL |