(24R)-Ergost-5-en-3β-ol
Campesterin · Ergost-5-en-3-ol · 24α-methyl Cholesterol · (24R)-Ergost-5-en-3β-ol · C01789 · CAMPESTROL · Campasterol · Campesterol
Identifikatoren & physikalische Daten
| CAS No. | 474-62-4 |
|---|---|
| Summenformel | C28H48O |
| Durchschnittliche Molmasse | 400,7 g/mol |
| Monoisotopische Masse | 400,37051615 g/mol |
| SMILES | CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C |
| InChIKey | SGNBVLSWZMBQTH-PODYLUTMSA-N |
| PubChem CID | 173183 |
| ChEMBL | CHEMBL520535 |
| ChEBI | CHEBI:28623 |
| EC No. | 207-484-4 |
| DTXSID | DTXSID801009891 |
| Lokaler Name | (24R)-Ergost-5-en-3β-ol |
Chemische & physikalische Eigenschaften
| XLogP | 8,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 29 |
| Formalladung | 0 |
| Komplexität | 620 |
| Stoffklassen | Biological Agents -> Plant Oils and Extracts |
| Lipide | Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Ergosterols and C24-methyl derivatives [ST0103] |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 157.5 °C156-160 °C |
| Physical Description | Solid[Merck Index] White crystalline solid[Sigma-Aldrich MSDS] |
| Siedepunkt | 463.29°C (rough estimate) |
| Dichte | 0.98±0.1 g/cm3 (20 ºC 760 Torr) |
| Brechungsindex | 1.5100 (estimate) |
| Lagerbedingungen | -20°C |
| Löslichkeit | Chloroform (Sparingly), Methanol (Slightly, Sonicated) |
| pKa (Säurekonstante) | 15.03±0.70(Predicted) |
| Aggregatzustand | crystalline |
| Farbe | white |
| Biologische Quelle | Glycine max (soybean) |
| Merck | 13,1736 |
| BRN | 3216975 |
| InChIKey | SGNBVLSWZMBQTH-ZRUUVFCLSA-N |
| SMILES | [H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])[C@H](C)CC[C@H](C)C(C)C |
| LogP (Verteilungskoeffizient) | 9.972 (est) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Ergost-5-en-3-ol, (3.beta.,24R)- |
| Gefahrenübersicht | Phytosterol esters containing 26-29% campesterol demonstrate no significant adverse effects in a 90-day oral study of ratsPhytosterol esters containing 27.9% campesterol produced decreased body weights, increased frequency of cardiomyopathy (males), and changes in hematology parameters in a 13-week oral study of rats at the highest tested dose (9,000 mg/kg/day)Phytosterol esters show no evidence of reproductive or developmental toxicity in rats[JECFA] A moderate irritantHarmful by ingestion, inhalation, and skin absorptionTargets the eyes, kidney, liver, and heart[Sigma-Aldrich MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 1888 6.1/PG 3 |
| Zollcode | 29061990 |
| R-Sätze (R) | 20/21/22-36/37/38-48/20/22-40-38-22 |
| Gefahrensymbole | Xn,T |
| Sicherheitshinweise (S) | 26-36-45-36/37/39-23 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
24α-methyl Cholesterol is a phytosterol found in vegetables, fruits, nuts, and seeds that competitively inhibits the absorption of intestinal cholesterol and decreases the transcription of genes important for cholesterol metabolism. The cholesterol lowering effects of phytosterols, such as 24α-methyl cholesterol, have been reported to be beneficial for lowering the incidence of atherosclerotic plaques. 24α-methyl Cholesterol can also act as an agonist at liver X receptors (LXR) and, through activation of LXR signaling, has been shown to suppress the proliferation of prostate and breast cancer cells.
Verwenden
Campesterol may be used as a plant sterol to test its effect on the transcriptional activation of liver X receptor α (LXRA) in breast cancer cells. It may also be used as a sterol standard for calibration curve generation in liquid chromatography multiple reaction monitoring (LC-MRM) analysis.