77058-74-3

Basic information

• Product Name: 24(S),25-Epoxycholesterol (not deuterated)
• Synonyms: 24(S),25-Epoxycholesterol (not deuterated);(24S)-24,25-Epoxycholest-5-en-3β-ol;(24S)-24,25-Epoxycholesterol;24S,25-EpoxyC;(24S)-24,25-Epoxycholestero;24(S);25-epoxycholesterol
• CAS NO: 77058-74-3
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.63706
• Mol File: 77058-74-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 496.4°C at 760 mmHg
• Flash Point: 201.2°C
• Appearance: /
• Density: 1.05
• Vapor Pressure: 6.18E-12mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (up to 30 mg/ml).
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.
• CAS DataBase Reference: 24(S),25-Epoxycholesterol (not deuterated)(CAS DataBase Reference)
• NIST Chemistry Reference: 24(S),25-Epoxycholesterol (not deuterated)(77058-74-3)
• EPA Substance Registry System: 24(S),25-Epoxycholesterol (not deuterated)(77058-74-3)

Safety Data

• Hazardous Substances Data: 77058-74-3(Hazardous Substances Data)

Usage

Description

24(S),25-Epoxycholesterol (not deuterated) is an oxysterol, a derivative of 4β-Hydroxy Cholesterol, which is a metabolite of Cholesterol. It is formed from Cholesterol by the drug-metabolizing enzyme cytochrome P 450 3A4. 24(S),25-Epoxycholesterol (not deuterated) is the most abundant oxysterol in mouse ventral midbrain and acts as a potential ligand for the nuclear receptor LXR. It is also recognized as a new endogenous CYP3A marker.

Uses

Used in Pharmaceutical Industry:
24(S),25-Epoxycholesterol (not deuterated) is used as a research compound for studying its role in activating liver X receptors (LXRs) in the developing ventral midbrain, which induces stem cell differentiation into dopaminergic neurons. This application is crucial for understanding the underlying mechanisms of neurodegenerative diseases and potential therapeutic interventions.
Used in Immunology Research:
In the field of immunology, 24(S),25-Epoxycholesterol (not deuterated) is used as an inhibitor for studying its effects on IL-6 production and degranulation of bone marrow-derived murine mast cells that express LXRβ. This helps researchers understand the compound's role in immune response regulation and its potential applications in treating immune-related disorders.
Used in Cell Biology and Biochemistry:
24(S),25-Epoxycholesterol (not deuterated) is used as a biochemical tool for investigating its inhibitory effects on the conversion of desmosterol to cholesterol by 3β-hydroxysterol Δ24-reductase (DHCR24/Seladin-1) in CHO-7 and SRD-1 cells. This application aids in understanding the compound's role in cellular cholesterol metabolism and its potential implications in various diseases associated with cholesterol imbalance.
Used in Drug Metabolism Studies:
As a ligand for the nuclear receptor LXR and an endogenous CYP3A marker, 24(S),25-Epoxycholesterol (not deuterated) is used in drug metabolism research to study the enzyme cytochrome P 450 3A4's role in the metabolism of various drugs and compounds. This application is essential for understanding drug-drug interactions and the development of more effective and safer pharmaceuticals.

References

1) Chawla et al. (2001), Nuclear receptors and lipid physiology: opening the X-files; Science, 294 1866 2) Brown et al. (2009), 24(S),25-epoxycholesterol: a messenger for cholesterol homeostasis; Int. J. Biochem. Cell Biol., 41 744 3) Theofilopoulos et al. (2013), Brain endogenous liver X receptor ligands selectively promote midbrain neurogenesis; Nature Chem. Biol., 9 126

InChI:InChI=1/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

Upstream product

• 64727-04-4 Δ⁵-3β,24(R),25-trihydroxycholestene-3-acetate 
• 313-04-2 demosterol 
• 5255-17-4 3β-hydroxy-5-cholenoic acid 
• 20231-57-6 methyl 5-cholenoate 
• 2665-04-5 demosterol acetate 
• 66414-43-5 3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol 
• 66414-44-6 3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-al 
• 51231-31-3 cholesta-5,24-diene-3β-ol 3-tetrahydropyran-2-yl ether 
• 66414-42-4 3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-oic acid methyl ester 
• 27460-33-9 3β-hydroxychol-5-en-24-al 
• 86476-29-1 3β-acetoxy-Δ⁵-cholenic aldehyde 
• 32345-19-0 24-ethylcholesta-5,22-dien-3β-ol 
• 51231-23-3 3α,5-cyclo-22-hydroxy-5α-23,24-bisnorcholan-6β-ol 6-methyl ether 
• 51231-25-5 3α,5-cyclo-22-iodo-5α-23,24-bisnorcholan-6β-ol 6-methyl ether 

Downstream Products

• 55651-21-3 Benzoic acid (3S,8S,9S,10R,13R,14S,17R)-17-[(R)-3-((S)-3,3-dimethyl-oxiranyl)-1-methyl-propyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 2140-46-7 25-hydroxychlolesterol 
• 474-73-7 24(S)-hydroxycholesterol 

Relevant articles and documents

Synthesis of 24-functionalized oxysterols

The syntheses of (24S)-24,25-epoxycholesterol, (24S)-hydroxycholesterol, and 24-ketocholesterol are described. The compounds belong to oxysterols, which can be considered to be the modulators of cholesterol metabolism. The asymmetric hydroxylation of desmosterol acetate according to Sharpless was used as the key reaction in the stereoselective introduction of functionality in position 24.

Efficient, stereoselective synthesis of 24(s), 25-epoxycholesterol

Efficient, stereoselective syntheses of 24(S), 25-epoxycholesterol (1) have been developed starting from cholenic acid (4) or stigmasterol (8), both featuring as the key step Sharpless asymmetric dihydroxylation of desmosterol acetate (2). This work permits preparation of gram quantities of 1 for further evaluation as a natural regulator of cholesterol metabolism, specifically, e.g., as a ligand for the LXRα. nuclear receptor.