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

Product Name24(S),25-Epoxycholesterol (not deuterated)
CAS77058-74-3
MFC27H44O2
MW400.64
EINECS
MOL File77058-74-3.mol

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).
form	White solid.
pka	15.03±0.70(predicted)
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.
InChIKey	OSENKJZWYQXHBN-XVYZBDJZSA-N
SMILES	O1[C@H](C1(C)C)CC[C@H]([C@@H]2[C@@]3([C@H]([C@H]4[C@@H]([C@]5(CC[C@@H](CC5=CC4)O)C)CC3)CC2)C)C

Safety Information

Storage Class

11 - Combustible Solids

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.

in vivo

24S,25-Epoxycholesterol (5 mM, icv) enhances the mDA neurogenesis, limits the neurodegeneration in CYP46A1-overexpressing mice midbrain^[4].

Animal Model:	GGPP induced mDA neurogenesis defect in CYP46A1 overexpressing CD-1 mice^[4]
Dosage:	5 mM
Administration:	icv, 1 μL, single dosage
Result:	Increased levels of mDA neurons, blocked the GGPP induced decrease of double EdU and TH cells.

References

[1] AJAY CHAWLA. Nuclear Receptors and Lipid Physiology: Opening the X-Files[J]. Science, 2001, 294 5548. DOI:10.1126/science.294.5548.1866
[2] BROWN A J. 24(S),25-Epoxycholesterol: A messenger for cholesterol homeostasis[J]. International Journal of Biochemistry & Cell Biology, 2009, 41 4: Pages 744-747. DOI:10.1016/j.biocel.2008.05.029
[3] SPYRIDON THEOFILOPOULOS. Brain endogenous liver X receptor ligands selectively promote midbrain neurogenesis[J]. Nature chemical biology, 2012, 9 2: 126-133. DOI:10.1038/nchembio.1156

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