Toosendanin
Chuanliansu · Toosendani · TOOSENDANIN · Toosendaninr · Toosendan extract · Toosendan Fructus。 · 28-Deacetylsendanin · Toosendanin USP/EP/BP
Identifikatoren & physikalische Daten
| CAS No. | 58812-37-6 |
|---|---|
| Summenformel | C30H38O11 |
| Durchschnittliche Molmasse | 574,6 g/mol |
| Monoisotopische Masse | 574,24141202 g/mol |
| SMILES | CC(=O)O[C@@H]1C[C@H](O)[C@@]23CO[C@@H](O)[C@]1(C)[C@@H]2C[C@@H](O)[C@]1(C)[C@@H]3C(=O)[C@H](OC(C)=O)[C@@]2(C)[C@H](c3ccoc3)C[C@H]3O[C@]321 |
| InChIKey | NAHTXVIXCMUDLF-RFNFAWMESA-N |
| PubChem CID | 9851101 |
| ChEMBL | CHEMBL503044 |
| ChEBI | CHEBI:192461 |
| EC No. | 683-199-2 |
| DTXSID | DTXSID00974333 |
Chemische & physikalische Eigenschaften
| XLogP | 0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 165 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 11 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 41 |
| Formalladung | 0 |
| Komplexität | 1.190 |
| Schmelzpunkt | 170-175°C |
| Siedepunkt | 555.97°C (rough estimate) |
| Dichte | 1.2084 (rough estimate) |
| Brechungsindex | 1.5970 (estimate) |
| Lagerbedingungen | Refrigerator |
| Löslichkeit | DMSO (Slightly), Methanol (Slightly) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 12.15±0.70(Predicted) |
| Farbe | White to Pale Beige |
| InChIKey | NAHTXVIXCMUDLF-VJLDGHPTNA-N |
| SMILES | C[C@@]1([C@H]2OC(C)=O)[C@]3([C@]([H])(O3)C[C@H]1C4=COC=C4)[C@]5(C)[C@H](O)C[C@@]6([H])[C@@](C)([C@@H]7O)[C@H](OC(C)=O)C[C@H](O)[C@]6(CO7)[C@@]5([H])C2=O |
| CAS Datenbank | 58812-37-6 |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Wassergefährdungsklasse (WGK) | WGK 3 |
| Zollcode | 29389090 |
| Sicherheitshinweise (S) | 24/25 |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrenklasse | Acute Tox. 3 Oral |
Anwendungen & Verwendung
Beschreibung
Fructus Meliae Toosendan (chuan lian zi), the fruit of Melia toosendan Sieb. Et Zucc, is mainly produced in Sichuan, Hubei, Henan, and Hunan province in China . Toosendanin is a tetracyclic triterpene compound extracted from fructus toosendan. It is an ascaridole agent and showed anti-botulinum, antibacterial, anticancer, and anti-inflammatory effects. It is also a neuromuscular blocking agent.
History
Toosendanin is the main chemical composition of the fructus toosendan. Researches on this compound could date back to 1953. Toosendanin has been named in 1955, while its structure was identified 20 years later by mass spectrometry. Toosendanin is a triterpenoid derivative containing a β-substituted furan ring . A new synthetic strategy is put forth allowing access to a 4-acetoxy CD fragment analogue of toosendanin, which was achieved from mesityl oxide and acetylacetone in 14 steps in 2009 . The anti-parasite of toosendanin was reported in 1971. In 1980, it was identified as a selective neuromuscular blocking agent that acts on neuromuscular junction . The anti-botulinum effect of toosendanin was discovered in 1982 . In recent years, it is also observed that toosendanin can induce differentiation and apoptosis . Toosendanin could inhibit the growth of feeding larvae and insects. It has been used as pollution-free, no residue of botanical insecticides for the production of fruits and vegetables in China .
Verwenden
Toosendanin is a triterpenoid derivative, acts as a novel agonist of L-type Ca2+ channels in neonatal rat ventricular cells.