(1R,3aR,4bR,5S,7aS,8R,9R,11S)-11-tert-Butyl-1,4b,8-trihydroxy-5-methyltetrahydro-3aH,4bH,9H-9,4a-(epoxymethano)cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-2,6,13(1H,5H)-trione
Grundinformationen
- CAS
15291-77-7- Standard-SMILES
C[C@@H]1C(=O)O[C@H]2[C@H](O)C34[C@H]5C[C@@H](C(C)(C)C)C36[C@@H](OC(=O)[C@@H]6O)OC4(C(=O)O5)[C@@]12O- InChIKey
SQOJOAFXDQDRGF-MAGGBRLHSA-N- Summenformel
- C20H24O10
- Durchschnittliche Molmasse
- 424,4 g/mol
- Monoisotopische Masse
- 424,13694696
Namen und Bezeichner
- Bevorzugter Name
- (1R,3aR,4bR,5S,7aS,8R,9R,11S)-11-tert-Butyl-1,4b,8-trihydroxy-5-methyltetrahydro-3aH,4bH,9H-9,4a-(epoxymethano)cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-2,6,13(1H,5H)-trione
- IUPAC
- (3R,6R,8S,10R,12R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione
- Englischer Name
- Ginkgolide B
- Summenformel
- C20H24O10
- Molmasse
- 424.4
Namen und Synonyme
EX-A6801HY-N0784CS-3724(1R,3aR,4bR,5S,7aS,8R,9R,11S)-11-tert-Butyl-1,4b,8-trihydroxy-5-methyltetrahydro-3aH,4bH,9H-9,4a-(epoxymethano)cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-2,6,13(1H,5H)-trioneBN 52021BGinkgolidGINKGOLIDE BGINKGOLIDE B(SH)7-DEOXYGINKGOLIDE CGINKOLIDE BBN 52021Ginkgolide B (BN-52021)
Weitere Namen anzeigen
Ginkgolide B (Standard)Ginkgolide B, 10 mM in DMSOGinkgolideA,1-hydroxy-, (1β)-
Datenbank-Bezeichner
- CAS
15291-77-7- PubChem CID
- 92044465
- DTXSID
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,4
- Polarare Oberfläche (TPSA)
- 149 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 10
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 30
- Formalladung
- 0
- Komplexität
- 925
Physikochemische Eigenschaften
- Schmelzpunkt
- 280 °C · 280°C (dec.)
- Siedepunkt
- 762.4 · 762.4±60.0 °C(Predicted)
- Dichte
- 1 · 1+-.0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 10 mg/ml).
- Aggregatzustand
- Solid
- pka
- 1 · pKa1 7.14; pKa2 8.60; pKa3 11.89(at 25℃)
- Farbe
- White
- Wasserlöslichkeit
- Soluble in DMSO. Slightly soluble in water and ethanol
- BRN
- 4727611 · 4727611
- Stabilität
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months
- InChIKey
- SQOJOAFXDQDRGF-MMQTXUMRSA-N
- SMILES
- [C@@]12(O)[C@]34C(=O)O[C@@H]5C[C@@H](C(C)(C)C)C6([C@@H](O)C(=O)O[C@@]6([H])O3)C45[C@H](O)[C@]1([H])OC(=O)[C@H]2C
- LogP
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- F
- 10-21
- wgk
- 3
- hs_code
- 29322090
- safety_code
- 24/25
Chemie und Industrie
Anwendungen
BeschreibungGinkgolide B is an important active ingredient derived from the leaf extract of Ginkgo biloba (Ginkgo biloba leaf extract, GBLPE), a member of the Ginkgoaceae family. It belongs to the class of terpenoid ketones and is a diterpene trilactone containing six five-membered rings in its molecular structure. The molecule comprises a spiro[4.4]nonane skeleton and a tetrahydrofuran ring, and is readily soluble in solvents such as ethyl acetate, methanol, ethanol, and dimethyl sulfoxide.
HistoryThe leaf of Ginkgo biloba is sweet, bitter, astringent, and mild. With activating blood circulation to remove blood stasis, dredging collaterals, relieving pain, and asthma, it is applied for treating blood stasis, chest pain, stroke, lung deficiency cough, and hyperlipidemia.As early as in the 1930s, scientists began to study ginkgo and harvest a variety of ginkgolide . Ginkgolide B was isolated and its structure illustrated by Wan Shan etal. in 1967. Subsequently, it was synthesized by Corey etal. in 1988. The preparation of effective components of Ginkgo biloba has been listed at home and abroad with development.The Ginkgo biloba extract consisting of ticlopidine is widely used in overseas market for the treatment of cerebral infarction. Intravenous injection of ginkgolide B is applied for the treatment of inflammation, but the project has been in the state, and there is no progress in it for many years. In addition, whether other extract of Ginkgo biloba can be used for the treatment of stable angina, cognitive impairment is still in preclinical research status.
VerwendenGinkgolide B is used as a potent PAF-R antagonist. Ginkgolide B speeds up PAF hydrolysis by promoting PAF-AH I α2 homodimer activity. Additionally, this compound has been reported to inhibit neutrophil degranulation in vitro. Inhibits superoxide production in vitro and inhibits bronchoconstriction and is neuroprotective following oral administration in vivo.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Zugehörige Reaktionen
0
Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.
Notizen zur Verbindung
Wird geladen…