5-α-Cholestan-3-β-ol
CHOLESTANOL · β-Cholestanol · BETA-CHOLESTANOL · 5alpha-Cholestanol · 5A-CHOLESTAN-3B-OL · 5α-Cholestan-3β-ol · Cholestan-3beta-ol · 5ALPHA-CHOLESTAN-3BETA-OL
Identifikatoren & physikalische Daten
| CAS No. | 80-97-7 |
|---|---|
| Summenformel | C27H48O |
| Durchschnittliche Molmasse | 388,7 g/mol |
| Monoisotopische Masse | 388,37051616 g/mol |
| SMILES | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C |
| InChIKey | QYIXCDOBOSTCEI-QCYZZNICSA-N |
| PubChem CID | 6665 |
| ChEMBL | CHEMBL1289436 |
| ChEBI | CHEBI:86570 |
| EC No. | 201-315-8 |
| DTXSID | DTXSID40883258 |
| Lokaler Name | 5-α-Cholestan-3-β-ol |
Chemische & physikalische Eigenschaften
| XLogP | 9,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 28 |
| Formalladung | 0 |
| Komplexität | 540 |
| Lipide | Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101] |
| Kosmetika | Emollient |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 140.0 - 142.0 °C138-142 °C |
| Physical Description | Solid |
| Ionization Efficiency | Positive0.042.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Collision Cross Section | 209 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 454.32°C (rough estimate) |
| Dichte | 0.9506 (rough estimate) |
| Brechungsindex | 1.5250 (estimate) |
| Lagerbedingungen | -20°C |
| Löslichkeit | chloroform: 0.1 g/mL, clear, colorlessInsoluble in water. |
| pKa (Säurekonstante) | 15.14±0.70(Predicted) |
| Aggregatzustand | A solid |
| Farbe | White to off-white |
| Biologische Quelle | synthetic (organic) |
| Merck | 14,2200 |
| BRN | 2418594 |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING - EMOLLIENTSKIN CONDITIONING |
| InChIKey | QYIXCDOBOSTCEI-QCYZZNICSA-N |
| SMILES | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C |
| LogP (Verteilungskoeffizient) | 10.065 (est) |
| CAS Datenbank | 80-97-7(CAS DataBase Reference) |
| NIST chemische Informationen | Cholestanol(80-97-7) |
| EPA chemische Informationen | Dihydrocholesterol (80-97-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | Not Classified |
|---|---|
| Hazard Classes and Categories | Not Classified |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1888 6.1/PG 3 |
| Zollcode | 2906 13 10 |
| RTECS-Nr. | FZ6350000 |
| R-Sätze (R) | 22-38-40-48/20/22-67-36/38-20-63 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 24/25-36/37-22-26 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Dihydrocholesterol (cholestanol; 5α-cholestan-3β-ol) is a cholesterol metabolite formed by oxidation and an intermediate in the biosynthesis of chenodeoxycholic acid . Cholestanol (10 μg/ml) induces apoptosis in cornea and lens epithelial cells and increases the activity of IL-1β converting enzyme (ICE) and CPP32 proteases. Dietary administration of 1% cholestanol to mice increases serum and liver cholestanol levels and leads to corneal opacities and gallstones and in rats it leads to cholestanol deposition in the cerebellum. Cholestanol levels are increased in plasma of patients with cerebrotendinous xanthomatosis (CTX), a disease characterized by a deficiency in the mitochondrial enzyme sterol 27-hydrolylase (CYP27A1) that leads to progressive neurological symptoms.
Verwenden
5α-Cholestan-3β-ol is a carbon stanol formed from biohydrogenation of Cholesterol (C432501) in the gut. Studies have also examined the conversion of 5α-Cholestan-3β-ol catalyzed by 3-β-hydroxysteroid dehydrogenase of rat liver.