(3β,24S)-Cholest-5-ene-3,24-diol

Product Name: (3β,24S)-Cholest-5-ene-3,24-diol
CAS No.: 474-73-7
Chemical Name: (3β,24S)-Cholest-5-ene-3,24-diol
Synonyms: 24-hydroxycholesterol;24(S)-HYDROXYCHOLESTEROL;5-CHOLESTEN-3β, 24(S)-DIOL;cholest-5-ene-3β,24(S)-diol;(24S)-24-hydroxycholesterol;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);24(S)-Hydroxycholesterol, Endogenous LXR agonist
CBNumber: CB6498177
Molecular Formula: C27H46O2
Formula Weight: 402.65
MOL File: 474-73-7.mol

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

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.

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML1648
Product name: 24(S)-Hydroxycholesterol
Purity: ≥98% (HPLC)
Packaging: 1MG
Price: $124.45
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML1648
Product name: 24(S)-Hydroxycholesterol
Purity: ≥98% (HPLC)
Packaging: 5MG
Price: $505.4
Updated: 2025/07/31

Cayman Chemical

Product number: 10009931
Product name: 24(S)-hydroxy Cholesterol
Purity: ≥95%
Packaging: 1mg
Price: $68
Updated: 2024/03/01

Cayman Chemical

Product number: 10009931
Product name: 24(S)-hydroxy Cholesterol
Purity: ≥95%
Packaging: 5mg
Price: $319
Updated: 2024/03/01

Cayman Chemical

Product number: 10009931
Product name: 24(S)-hydroxy Cholesterol
Purity: ≥95%
Packaging: 10mg
Price: $601
Updated: 2024/03/01

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

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

(3β,24S)-Cholest-5-ene-3,24-diol Preparation Products And Raw materials

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View Lastest Price from (3β,24S)-Cholest-5-ene-3,24-diol manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: (3β,24S)-Cholest-5-ene-3,24-diol 474-73-7
Price: US $1.00-22.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100000KG
Release date: 2024-08-02

474-73-7, (3β,24S)-Cholest-5-ene-3,24-diolRelated Search:

Thapsigargin Endosidin 2 SALUBRINAL U 18666A 1-Hexene Sodium cholate Inositol Aminophylline 24(S),25-Epoxycholesterol (not deuterated) 24(S),25-EPOXYCHOLESTEROL (3β,24S)-Cholest-5-ene-3,24-diol HYDROXYCHOLESTEROL 24(S), [24-3H]

(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 (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

24(S)-HYDROXYCHOLESTEROL

(3β,24S)-Cholest-5-ene-3,24-diol

Cholest-5-ene-3,24-diol, (3β,24S)-

5-CHOLESTEN-3β, 24(S)-DIOL

24(S)-Hydroxycholesterol, Endogenous LXR agonist

474-73-7

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