(3β,24S)-Cholest-5-ene-3,24-diol Chemical Properties

Melting point:

174-176 °C

Boiling point:

513.1±23.0 °C(Predicted)

Density 

1.03±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in DMSO (up to 10 mg/ml) or in Ethanol (up to 10 mg/ml).

form 

powder

pka

15.03±0.70(Predicted)

color 

white to beige

optical activity

[α]/D -45 to -52°, c = 1 in chloroform-d

Stability:

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

(3β,24S)-Cholest-5-ene-3,24-diol Usage And Synthesis

Description

24(S)-hydroxy Cholesterol is a side-chain substituted oxysterol that has important roles in cholesterol homeostasis. It is generated by the action of CYP46 on cholesterol in the brain and diffuses across the blood-brain barrier to the systemic circulation where it can modulate cell signaling, be used for further sterol biosynthesis, or be metabolized in the liver. 24(S)-hydroxy cholesterol potently activates LXRα and LXRβ nuclear receptors (EC₅₀ = 4 and 3 μM, respectively), causing upregulation of cholesterol-lowering genes. In the brain, this oxysterol controls cholesterol processing to facilitate neurological repair during Alzheimer’s disease and other neuropathological conditions.

Uses

(3β,24S)-Cholest-5-ene-3,24-diol is used as a biomarker in the analysis of disease.

Uses

(3β,24S)-Cholest-5-ene-3,24-diol is used as a biomarker in the analysis of disease.

Definition

ChEBI: (24S)-24-hydroxycholesterol is a 24-hydroxycholesterol that has S configuration at position 24. It is the major metabolic breakdown product of cholesterol in the brain. It has a role as a mouse metabolite, a biomarker and a human blood serum metabolite.

General Description

24(S)-hydroxycholesterol (24HC) is synthesized from cholesterol in brain dendrites by the action of enzyme cholesterol 24-hydroxylase (CYP46A1). It is catabolized to bile acids in the liver.

Biochem/physiol Actions

24(S)-hydroxycholesterol (24HC) elevated levels are reported in liver inflammation and fibrosis. It is a N-methyl-D-aspartate receptor (NMDAR) modulator. The levels of 24HC are potential indicators of brain development as well as pathology including Alzheimer′s disease (AD) and multiple sclerosis. Polymorphism in the cholesterol 24-hydroxylase (CYP46A1) gene leads to elevated 24HC levels and toxicity. 24HC is a mediator of apoptosis and necroptosis. Elevated levels of 24HC are reported in liver inflammation and fibrosis.

References

[1] D LÜTJOHANN. Cholesterol homeostasis in human brain: evidence for an age-dependent flux of 24S-hydroxycholesterol from the brain into the circulation.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1996, 93 18: 9799-9804. DOI:10.1073/pnas.93.18.9799
[2] AJAY CHAWLA. Nuclear Receptors and Lipid Physiology: Opening the X-Files[J]. Science, 2001, 294 5548. DOI:10.1126/science.294.5548.1866
[3] HEIKE KÖLSCH . The neurotoxic effect of 24-hydroxycholesterol on SH-SY5Y human neuroblastoma cells[J]. Brain Research, 1999, 818 1: Pages 171-175. DOI:10.1016/s0006-8993(98)01274-8
[4] KAZUNORI YAMANAKA. 24(S)-hydroxycholesterol induces neuronal cell death through necroptosis, a form of programmed necrosis.[J]. The Journal of Biological Chemistry, 2011: 24666-24673. DOI:10.1074/jbc.m111.236273
[5] A second class of nuclear receptors for oxysterols: regulation of RORalpha and RORgamma activity by 24(S)-hydroxycholesteraol (cerebrosterol)
[6] VALERIO LEONI  Claudio C. Potential diagnostic applications of side chain oxysterols analysis in plasma and cerebrospinal fluid[J]. Biochemical pharmacology, 2013, 86 1: Pages 26-36. DOI:10.1016/j.bcp.2013.03.015
[7] YASUOMI URANO  Noriko N  Sachika Ochiai. Suppression of amyloid-β production by 24S-hydroxycholesterol via inhibition of intracellular amyloid precursor protein trafficking[J]. FASEB Journal, 2013, 27 10: 4305-4315. DOI:10.1096/fj.13-231456

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