15291-76-6

Basic information

• Product Name: Ginkgolide C
• Synonyms: GINKGOLIDE C;1,7-DIHYDROXY-GINKGOLIDE A;bn52022;(1S,2R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11R,11aR)-3-(1,1-Dimethylethyl)hexahydro-2,4,7b,11-tetrahydroxy-8-methyl-9H-1,7a-(epoxymethano)-1H,6aH-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-5,9,12(4H)-trione;Gingkolide C;GinkgolideA,1,7-dihydroxy-, (1α,7β)-;Ginkgolide C,1,7-Dihydroxy-ginkgolide A;CGinkgolid
• CAS NO: 15291-76-6
• Molecular Formula: C₂₀H₂₄O₁₁
• Molecular Weight: 440.4
• Product Categories: Saponins;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 15291-76-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: >3000 (dec)
• Boiling Point: 813.8 °C at 760 mmHg
• Flash Point: 291.4 °C
• Appearance: crystalline solid
• Density: 1.72 g/cm³
• Vapor Pressure: 1.15E-30mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly, Heated)
• PKA: 10.88±0.70(Predicted)
• CAS DataBase Reference: Ginkgolide C(CAS DataBase Reference)
• NIST Chemistry Reference: Ginkgolide C(15291-76-6)
• EPA Substance Registry System: Ginkgolide C(15291-76-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 15291-76-6(Hazardous Substances Data)

Usage

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. It is a crystalline solid.

Uses

Used in Pharmaceutical Industry:
Ginkgolide C is used as a reference compound for PAF receptors in biological systems, making it a valuable tool for research and development in the pharmaceutical industry.
Used in Cardiovascular and Cerebrovascular Treatments:
Ginkgolide C is used as a family of bioactive terpenes for treating cardiovascular and cerebrovascular diseases. It acts as a specific platelet activating factor (PAF) antagonist, which can help in the treatment and management of these conditions.

InChI:InChI=1/C20H24O11/c1-5-12(24)28-11-8(22)18-10-6(21)7(16(2,3)4)17(18)9(23)13(25)30-15(17)31-20(18,14(26)29-10)19(5,11)27/h5-11,15,21-23,27H,1-4H3/t5-,6-,7+,8?,9?,10-,11+,15+,17?,18?,19-,20+/m1/s1

Upstream product

• 502421-88-7 10-benzyloxy-ginkgolide C 

Downstream Products

• 502421-88-7 10-benzyloxy-ginkgolide C 
• 693259-76-6 10-(4-methoxy-benzyloxy)-ginkgolide C 
• 153355-67-0 7-Acetoxy-1-(tert-butyldiphenylsilyloxy)-10-hydroxy-3,14-didehydroginkgolid 
• 153355-66-9 7-Acetoxy-1-(tert-butyldiphenylsilyloxy)-3,10-dihydroxyginkgolid 
• 15291-78-8 ginkgolide M 
• 153541-09-4 1,7,10-Trihydroxy-14-epiginkgolid 
• 15291-77-7 ginkgolide B 
• 130523-05-6 1-O-(tert-Butyldiphenylsilyl)-7-O-(phenyloxythiocarbonyl)ginkgolid C 
• 130523-06-7 1-O-(tert-Butyldiphenylsilyl)ginkgolid B 
• 145497-38-7 C₃₅H₃₁F₅O₁₃S 
• 145473-36-5 C₂₈H₃₂O₁₁ 
• 693260-01-4 7-(4-nitro-phenoxycarbonyloxy)-10-(4-methoxy-benzyloxy)-ginkgolide C 
• 693260-12-7 1-(piperidine-carbonyloxy)-10-(4-methoxy-benzyloxy)-GC 

Relevant articles and documents

Isolation of ginkgolides A, B, C, J and bilobalide from G. biloba extracts

Ginkgolides A, B, C and J, together with bilobalide, are unique terpenoid components of the Ginkgo biloba tree. Due to similar chemical properties, their separation is quite tedious. We have developed an efficient and rapid protocol for separation of individual ginkgolides and bilobalide from G. biloba extracts. The procedure takes advantage of enhanced susceptibility of ginkgolides B and C to benzylation and the ease of separation of these products from ginkgolides A and J which do not react. The protocol is applicable to the previously reported enriched extracts prepared from G. biloba leaves. A single chromatographic step prior to benzylation provides bilobalide and mixture of ginkgolides A, B, C, and J. After benzylation, the individual ginkgolides are separated by chromatography.