502421-88-7

Basic information

• Product Name: 10-benzyloxy-ginkgolide C
• Synonyms: 10-benzyloxy-ginkgolide C
• CAS NO: 502421-88-7
• Molecular Weight: 530.529
• Mol File: 502421-88-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 10-benzyloxy-ginkgolide C(CAS DataBase Reference)
• NIST Chemistry Reference: 10-benzyloxy-ginkgolide C(502421-88-7)
• EPA Substance Registry System: 10-benzyloxy-ginkgolide C(502421-88-7)

Safety Data

• Hazardous Substances Data: 502421-88-7(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 15291-76-6 1,3,7,10-Tetrahydroxyginkgolid 
• 100-44-7 benzyl chloride 

Downstream Products

• 15291-76-6 1,3,7,10-Tetrahydroxyginkgolid 
• 693259-91-5 7-(4-nitro-phenoxycarbonyloxy)-10-benzyloxy-glinkgolide C 

Relevant articles and documents

Preparation of 7-substituted ginkgolide derivatives: Potent platelet activating factor (PAF) receptor antagonists

Ginkgolides are structurally unique constituents of Ginkgo biloba extracts and are known antagonists of the platelet-activating factor (PAF) receptor. Ginkgolide C is 25-fold less potent than ginkgolide B as a PAF receptor antagonist, due to the presence of the 7fi-OH. Recently, we found that 7α-fluoro ginkgolide B was equipotent to ginkgolide B underlining the critical importance of the 7-position of ginkgolides for PAF receptor activity. Herein we describe the synthesis of a series of ginkgolide B derivatives with modifications at the 7-position and the pharmacological evaluation of these derivatives as assayed by cloned PAF receptors. In two cases nucleophilic attack on a 7β-O-triflate ginkgolide B did not lead to the expected products, but gave rise to two unprecedented ginkgolide derivatives, one with a novel rearranged skeleton. Furthermore, standard reduction of 7α-azido ginkgolide B did not give the expected primary amine, but instead yielded alkylated amines depending on the solvent employed. Pharmacological testing with cloned PAF receptors showed that ginkgolides with 7α-substitutents had increased affinity compared to 7β-substituents, in particular 7α-chloro ginkgolide B, the most potent nonaromatic ginkgolide derivative described to date with a Ki value of 110 nM.

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.