24(S)-hydroxycholesterol

Base Information

• Chemical Name: 24(S)-hydroxycholesterol
• CAS No.: 474-73-7
• Molecular Formula: C27H46 O2
• Molecular Weight: 402.661
• UNII: 47IMW63S3F
• DSSTox Substance ID: DTXSID101313419
• Nikkaji Number: J637.349F
• Wikipedia: 24S-Hydroxycholesterol
• Wikidata: Q27071873
• Pharos Ligand ID: 2HMFXFCTGQTD
• Metabolomics Workbench ID: 34379
• ChEMBL ID: CHEMBL171804
• Mol file: 474-73-7.mol

Synonyms:24-hydroxycholesterol;24S-hydroxycholesterol;cerebrosterol;cholest-5-ene-3,24-diol

Chemical Property of 24(S)-hydroxycholesterol

Chemical Property:

• Vapor Pressure: 1.13E-12mmHg at 25°C
• Melting Point: 174-176 °C
• Boiling Point: 513.1°C at 760 mmHg
• PKA: 15.03±0.70(Predicted)
• Flash Point: 213.5°C
• PSA: 40.46000
• Density: 1.03g/cm³
• LogP: 6.35950
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 10 mg/ml) or in Ethanol (up to 10 mg/ml).
• XLogP3: 7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 402.349780706
• Heavy Atom Count: 29
• Complexity: 624

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3β,24S)-Cholest-5-ene-3,24-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
• Isomeric SMILES: C[C@H](CC[C@@H](C(C)C)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
• 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.

Technology Process of 24(S)-hydroxycholesterol

There total 6 articles about 24(S)-hydroxycholesterol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

(24S)-24,25-epoxycholesterol (77058-74-3,72542-49-5) → 25-hydroxychlolesterol (2140-46-7) + 24(S)-hydroxycholesterol (474-73-7)

Guidance literature:

(24S)-24,25-epoxycholesterol; With hydrogen bromide; In chloroform; acetic acid; at 20 ℃; for 1.5h;

With azobisisobutyronitrile; tri-n-butyl-tin hydride; In benzene; for 1h; Heating;

DOI:10.1023/A:1015720707433

Reference yield:

→ 24(S)-hydroxycholesterol (474-73-7) + 24(R)-Hydroxycholesterol (27460-26-0)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol;

DOI:10.1021/ja01109a515 DOI:10.1021/ja01233a018

Reference yield:

propan-1-ol (71-23-8) → 24(S)-hydroxycholesterol (474-73-7) + 24(R)-Hydroxycholesterol (27460-26-0)

Guidance literature:

With sodium;

upstream raw materials:

3β-acetoxy-cholest-5-en-24-one

aluminum isopropoxide

isopropyl alcohol

propan-1-ol

Downstream raw materials:

(24S)-7-oxocholest-5-en-3β,24-diyl dibenzoate

(24S)-cholest-5-ene-3β,7α,24-triol 3β,24-dibenzoate

(24S)-cholest-5-ene-3β,24-diyl dibenzoate

Refernces

• 1、 Koizumi,Morisaki,Ikekawa,et al.. "Absolute configurations of 24 hydroxycholesterol and related compounds". . p. 2203 - 2206. Retrieved 2007/10/12.