| Identification | Back Directory | [Name]
(3β,24S)-Cholest-5-ene-3,24-diol | [CAS]
474-73-7 | [Synonyms]
24-hydroxycholesterol
24(S)-HYDROXYCHOLESTEROL
(24S)-24-hydroxycholesterol
cholest-5-ene-3β,24(S)-diol
cholest-5-ene-3-beta,24-diol
(3β,24S)-Cholest-5-ene-3,24-diol
Cholest-5-ene-3,24-diol, (3β,24S)-
24(S)-hydroxycholesterol (24(S)-HC)
CHOLEST-5-ENE-3Β,24(S)-DIOL;24(S)-HYDROXYCHOLESTEROL
(8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4S)-4-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-hydroxy-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | [Molecular Formula]
C27H46O2 | [MDL Number]
MFCD03695560 | [MOL File]
474-73-7.mol | [Molecular Weight]
402.65 |
| Chemical Properties | Back Directory | [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. |
| Hazard Information | Back Directory | [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.
| [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) Lujohann et al. (1996), Cholesterol homeostasis in human brain: evidence for an age-dependent flux of 24S-hydroxycholesterol from the brain into circulation; Proc. Natl. Acad. Sci. USA, 93 9799
2) Chawla et al. (2001), Nuclear receptors and lipid physiology:opening the X-files; Science, 294 1866
3) Kolsch et al. (1999), The neurotoxic effect of 24-hydroxycholesterol on SH-SY5Y human neuroblastoma cells; Brain Res., 818 171
4) Yamanaka et al. (2011), 24(S)-hydroxycholesterol induces neuronal cell death through necroptosis, a form of programmed necrosis; J. Biol. Chem., 286 24666
5) Wang et al. (2010), A second class of nuclear receptors for oxysterols: regulation of RORalpha and RORgamma activity by 24(S)-hydroxycholesteraol (cerebrosterol); Biochim. Biophys. Acta, 1801 917
6) Leoni and Caccia (2013), Potential diagnostic applications of side chain oxysterols analysis in plasma and cerebrospinal fluid; Biochem. Pharmacol., 86 26
7) Urano et al. (2013), Suppression of amyloid-β production by 24S-hydroxycholesterol via inhibition of intracellular amyloid precursor protein trafficking; FASEB J.,?27?4305 |
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