Ginkgolide C

Base Information

• Chemical Name: Ginkgolide C
• CAS No.: 15291-76-6
• Molecular Formula: C20H24O11
• Molecular Weight: 440.404
• Hs Code.: 29322090
• European Community (EC) Number: 604-875-5
• UNII: 32ZQ957R4A
• Wikidata: Q104914776
• Metabolomics Workbench ID: 149952
• ChEMBL ID: CHEMBL4765159
• Mol file: 15291-76-6.mol

Synonyms:BN 52022;BN-52022;ginkgolide C

Chemical Property of Ginkgolide C

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 1.15E-30mmHg at 25°C
• Melting Point: >3000 °C
• Refractive Index: 1.671
• Boiling Point: 813.8 °C at 760 mmHg
• PKA: 10.88±0.70(Predicted)
• Flash Point: 291.4 °C
• PSA: 169.05000
• Density: 1.72 g/cm³
• LogP: -2.39870
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly, Heated)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 1
• Exact Mass: 440.13186158
• Heavy Atom Count: 31
• Complexity: 957

Purity/Quality:

more than 98% ^*data from raw suppliers

Ginkgolide C ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)OC2C1(C34C(=O)OC5C3(C2O)C6(C(C5O)C(C)(C)C)C(C(=O)OC6O4)O)O
• Isomeric SMILES: C[C@@H]1C(=O)O[C@@H]2[C@]1([C@@]34C(=O)O[C@H]5[C@]3([C@H]2O)[C@@]6([C@@H]([C@H]5O)C(C)(C)C)[C@H](C(=O)O[C@H]6O4)O)O
• Description: Ginkgolide C is a flavone first extracted from G. biloba leaves with multiple reported biological functions. It has been identified as a selective platelet activating factor receptor antagonist (IC50 = 37.6 μM). Ginkgolide C has also been shown to increase lipolysis and to inhibit adipogenesis in adipocytes via the activated AMPK pathway.
• Uses: Reference compound for PAF receptors in biological systems. Family of bioactive terpenes treating cardiovascular and cerebrovascular diseases. Specific platelet activating factor (PAF) antagonists.

Technology Process of Ginkgolide C

There total 1 articles about Ginkgolide C which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

10-benzyloxy-ginkgolide C (502421-88-7) → 1,3,7,10-Tetrahydroxyginkgolid (15291-76-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 20h; under 2888 Torr;

DOI:10.1016/j.phytochem.2004.08.026

Reference yield: 97.0%

2-chloromethylpyridine (4377-33-7) + 1,3,7,10-Tetrahydroxyginkgolid (15291-76-6) → 10-(2-pyridinyl-methoxy)-ginkgolide C

Guidance literature:

With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20 - 60 ℃; for 15h;

Reference yield: 95.0%

Ginkgolide C (15291-76-6) + tert-butylchlorodiphenylsilane (58479-61-1) → 1-O-(tert-Butyldiphenylsilyl)ginkgolid C (130523-04-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 48h;

upstream raw materials:

10-benzyloxy-ginkgolide C

Downstream raw materials:

C₂₈H₃₂O₁₂

C₂₈H₃₂O₁₂

1-O-(tert-Butyldiphenylsilyl)ginkgolid C

1-(tert-butyldiphenylsilyloxy)-3,7,10-trihydroxyginkgolid

Refernces