474-73-7

Basic information

• Product Name: 24(S)-HYDROXYCHOLESTEROL
• Synonyms: 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;(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;cholest-5-ene-3β,24(S)-diol;(24S)-24-hydroxycholesterol;24(S)-hydroxycholesterol (24(S)-HC);(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 NO: 474-73-7
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 402.65294
• Product Categories: Pharmaceutical Raw Materials;Diagnostic
• Mol File: 474-73-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 174-176 °C
• Boiling Point: 513.1°C at 760 mmHg
• Flash Point: 213.5°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 1.13E-12mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (up to 10 mg/ml) or in Ethanol (up to 10 mg/ml).
• PKA: 15.03±0.70(Predicted)
• 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.
• CAS DataBase Reference: 24(S)-HYDROXYCHOLESTEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 24(S)-HYDROXYCHOLESTEROL(474-73-7)
• EPA Substance Registry System: 24(S)-HYDROXYCHOLESTEROL(474-73-7)

Safety Data

• Hazardous Substances Data: 474-73-7(Hazardous Substances Data)

Usage

Description

24(S)-HydroxycholeSTEROL is a side-chain substituted oxysterol that plays a crucial role in cholesterol homeostasis. It is produced by the action of CYP46 on cholesterol in the brain and can cross 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. This oxysterol potently activates LXRα and LXRβ nuclear receptors, leading to the upregulation of cholesterol-lowering genes. In the brain, it controls cholesterol processing to support neurological repair during Alzheimer's disease and other neuropathological conditions.

Uses

Used in Pharmaceutical Industry:
24(S)-HydroxycholeSTEROL is used as a therapeutic agent for modulating cholesterol homeostasis and activating LXRα and LXRβ nuclear receptors, which can help in the treatment of various cholesterol-related disorders.
Used in Neurological Research:
24(S)-HydroxycholeSTEROL is used as a research tool for studying the role of cholesterol processing in neurological repair during Alzheimer's disease and other neuropathological conditions.
Used as a Biomarker in Medical Analysis:
(3β,24S)-Cholest-5-ene-3,24-diol, also known as 24(S)-HydroxycholeSTEROL, is used as a biomarker in the analysis of diseases, particularly those related to cholesterol metabolism and neurological conditions.

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

InChI:InChI=1/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1

Upstream product

• 20981-59-3 3β-acetoxy-cholest-5-en-24-one 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 71-23-8 propan-1-ol 
• 77058-74-3 (24S)-24,25-epoxycholesterol 

Downstream Products

• 27460-29-3 (24S)-cholest-5-ene-3β,24-diyl dibenzoate 
• 306288-43-7 (24S)-7-oxocholest-5-en-3β,24-diyl dibenzoate 
• 306288-46-0 (24S)-cholest-5-ene-3β,7α,24-triol 3β,24-dibenzoate 

Relevant articles and documents

Synthesis of 24-functionalized oxysterols

The syntheses of (24S)-24,25-epoxycholesterol, (24S)-hydroxycholesterol, and 24-ketocholesterol are described. The compounds belong to oxysterols, which can be considered to be the modulators of cholesterol metabolism. The asymmetric hydroxylation of desmosterol acetate according to Sharpless was used as the key reaction in the stereoselective introduction of functionality in position 24.