Lup-20(29)-en-3,28-diol, (3β)-
TROCHOL · Betuline · Birch bark extract · BETULINOL · betula camphor · Betulinic alcohol · (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol · BetuL
Identifikatoren & physikalische Daten
| CAS No. | 473-98-3 |
|---|---|
| Summenformel | C30H50O2 |
| Durchschnittliche Molmasse | 442,7 g/mol |
| Monoisotopische Masse | 442,38108083 g/mol |
| SMILES | C=C(C)[C@@H]1CC[C@]2(CO)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12 |
| InChIKey | FVWJYYTZTCVBKE-ROUWMTJPSA-N |
| PubChem CID | 72326 |
| ChEMBL | CHEMBL23236 |
| ChEBI | CHEBI:3086 |
| EC No. | 207-475-5 |
| DTXSID | DTXSID101019934 |
| Lokaler Name | Lup-20(29)-en-3,28-diol, (3β)- |
Chemische & physikalische Eigenschaften
| XLogP | 8,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 32 |
| Formalladung | 0 |
| Komplexität | 786 |
| Siedepunkt | 284.00 to 288.00 °C. @ 743.00 mm Hg493.26°C (rough estimate) |
| Schmelzpunkt | 251 - 252 °C256-257 °C(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 193.57 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]208.3 Ų [M+Na]+ [CCS Type: TW |
| Dichte | 0.9882 (rough estimate) |
| Brechungsindex | 1.5045 (estimate) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Chloroform (Slightly), Methanol (Slightly, Heated) |
| Aggregatzustand | Off-white powder |
| pKa (Säurekonstante) | 15.10±0.10(Predicted) |
| Farbe | Pale Brown to Beige |
| Merck | 14,1189 |
| Stabilität | Hygroscopic |
| Hauptanwendungen | food and beverages |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING |
| InChIKey | FVWJYYTZTCVBKE-ROUWMTJPSA-N |
| SMILES | [H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@@]5(CO)CC[C@@H](C(C)=C)[C@]25[H] |
| LogP (Verteilungskoeffizient) | 8.607 (est) |
| CAS Datenbank | 473-98-3(CAS DataBase Reference) |
| NIST chemische Informationen | Betulin(473-98-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | Not ClassifiedReported as not meeting GHS hazard criteria by 27 of 31 companiesAggregated GHS information provided per 31 reports by companies from 4 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 27 of 31 reports by companies.There are 3 notifications provided by 4 of 31 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Not Classified |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29181985 |
| RTECS-Nr. | OK5755000 |
| R-Sätze (R) | 36/37/38-20/21/22-68/20/21/22-68 |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 36/37-36-26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | STOT SE 2 |
Anwendungen & Verwendung
Beschreibung
Sterol regulatory element binding protein 2 (SREBP-2) regulates cholesterol synthesis by activating the transcription of genes for HMG-CoA reductase and other enzymes of the cholesterol synthetic pathway. When cellular sterol levels are high, SREBP is bound by SCAP and Insig to ER membranes as a glycosylated precursor protein. Upon cholesterol depletion, the protein is cleaved to its active form and translocated into the nucleus to stimulate transcription of genes involved in the uptake and synthesis of cholesterol. Betulin, the precursor of betulinic acid, is a pentacyclic triterpene found in the bark of birch trees. Betulin inhibits the SREBP-driven pathway of cholesterol and fatty acid biosynthesis by promoting SCAP–Insig binding which prevents the activation and release of SREBP-2 from the ER. At 15-30 mg/kg/day, betulin has been shown to decrease lipid levels and increase insulin sensitivity in mice fed a western-type diet. In an atherosclerosis disease model, 30 mg/kg/day betulin can reduce the size and improve the stability of atherosclerotic plaques in LDLR-knockout mice. At 2.5-5 μg/ml betulin, in combination with cholesterol, demonstrates anticancer effects by inducing apoptosis in Jurkat cells, A549 lung carcinoma cells, and HeLa cervical carcinoma cells.
Verwenden
Betulin may be used in the preparation of betulinic acid, which shows anti-HIV, antimalarial and anti-inflammatory activities.