24(S),25-Epoxycholesterol (not deuterated) Chemical Properties

Melting point:

156-157 °C

Boiling point:

496.4±18.0 °C(predicted)

Density 

1.05

storage temp. 

-20°C

solubility 

Soluble in DMSO (up to 30 mg/ml).

pka

15.03±0.70(predicted)

form 

White solid.

color 

White

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.

24(S),25-Epoxycholesterol (not deuterated) Usage And Synthesis

Description

24(S),25-epoxy Cholesterol is an oxysterol and the most abundant oxysterol in mouse ventral midbrain. It activates liver X receptors (LXRs) in the developing ventral midbrain to induce stem cell differentiation into dopaminergic neurons. 24(S),25-epoxy Cholesterol inhibits IL-6 production and degranulation of bone marrow-derived murine mast cells that express LXRβ. It inhibits the conversion of desmosterol to cholesterol by 3β-hydroxysterol Δ²⁴-reductase (DHCR24/Seladin-1) in CHO-7 and SRD-1 cells when used at a concentration of 2.5 μM.

Uses

(24S)-24,25-Epoxycholesterol is a derivative of 4β-Hydroxy Cholesterol (H917980), a metabolite of Cholesterol. It is formed from Cholesterol by the drug-metabolizing enzyme cytochrome P 450 3A4. A potential ligand for the nuclear receptor LXR and also a new endogenous CYP3A marker.

Definition

ChEBI: A 3beta-hydroxy 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.

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

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