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Product Name:(3S,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
CAS:474-73-7
Purity:95% Package:100g; 1kg Remarks:LN01265570
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| | (3β,24S)-Cholest-5-ene-3,24-diol Basic information |
| Product Name: | (3β,24S)-Cholest-5-ene-3,24-diol | | Synonyms: | (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;24-hydroxycholesterol;cholest-5-ene-3-beta,24-diol;(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;cholest-5-ene-3β,24(S)-diol;CHOLEST-5-ENE-3Β,24(S)-DIOL;24(S)-HYDROXYCHOLESTEROL;(24S)-24-hydroxycholesterol;24(S)-HYDROXYCHOLESTEROL | | CAS: | 474-73-7 | | MF: | C27H46O2 | | MW: | 402.65 | | EINECS: | | | Product Categories: | Pharmaceutical Raw Materials;Diagnostic | | Mol File: | 474-73-7.mol |  |
| | (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) 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 |
| | (3β,24S)-Cholest-5-ene-3,24-diol Preparation Products And Raw materials |
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