MedKoo Cat#: 540163 | Name: Ginkgolide C
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ginkgolide C is a GABA-A receptor, α-1 GlyR, and PAF receptor antagonist found in Ginkgo. It suppresses production of TxA2 to inhibit platelet aggregation and inhibits formation of superoxide and hydroxyl radicals.

Chemical Structure

Ginkgolide C
Ginkgolide C
CAS#15291-76-6

Theoretical Analysis

MedKoo Cat#: 540163

Name: Ginkgolide C

CAS#: 15291-76-6

Chemical Formula: C20H24O11

Exact Mass: 440.1319

Molecular Weight: 440.40

Elemental Analysis: C, 54.55; H, 5.49; O, 39.96

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
25mg USD 950.00 2 Weeks
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Synonym
Ginkgolide C; Ginkgolide-C; 1,7-dihydroxy Ginkgolide A; BN-52022; BN52022; BN 52022;
IUPAC/Chemical Name
(1R,3R,6R,7S,8S,9R,10S,11R,12R,13S,16S,17R)-8-tert-butyl-6,9,12,17-tetrahydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione
InChi Key
AMOGMTLMADGEOQ-BLHJUYJRSA-N
InChi Code
InChI=1S/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
SMILES Code
O=C(O1)[C@@H](C)[C@@]2(O)[C@]1([H])[C@H](O)C34[C@@]25O[C@@]6([H])C3([C@@H](O)C(O6)=O)[C@H](C(C)(C)C)[C@@H](O)[C@H]4OC5=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 440.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Liou CJ, Lai XY, Chen YL, Wang CL, Wei CH, Huang WC. Ginkgolide C Suppresses Adipogenesis in 3T3-L1 Adipocytes via the AMPK Signaling Pathway. Evid Based Complement Alternat Med. 2015;2015:298635. doi: 10.1155/2015/298635. Epub 2015 Aug 30. PubMed PMID: 26413119; PubMed Central PMCID: PMC4568043. 2: Li J, Li D, Hu J, Bi Y, Xiao W, Wang Z. Simultaneous determination of ginkgolides A, B, C and bilobalide by LC-MS/MS and its application to a pharmacokinetic study in rats. Biomed Chromatogr. 2015 Dec;29(12):1907-12. doi: 10.1002/bmc.3515. Epub 2015 Jul 23. PubMed PMID: 26010697. 3: Huang P, Zhang L, Chai C, Qian XC, Li W, Li JS, Di LQ, Cai BC. Effects of food and gender on the pharmacokinetics of ginkgolides A, B, C and bilobalide in rats after oral dosing with ginkgo terpene lactones extract. J Pharm Biomed Anal. 2014 Nov;100:138-44. doi: 10.1016/j.jpba.2014.07.030. Epub 2014 Aug 2. PubMed PMID: 25165009. 4: Ma S, Liu X, Xu Q, Zhang X. Transport of ginkgolides with different lipophilicities based on an hCMEC/D3 cell monolayer as a blood-brain barrier cell model. Life Sci. 2014 Oct 2;114(2):93-101. doi: 10.1016/j.lfs.2014.08.006. Epub 2014 Aug 17. PubMed PMID: 25139831. 5: Lau AJ, Yang G, Yap CW, Chang TK. Selective agonism of human pregnane X receptor by individual ginkgolides. Drug Metab Dispos. 2012 Jun;40(6):1113-21. doi: 10.1124/dmd.112.045013. Epub 2012 Mar 5. PubMed PMID: 22393123. 6: Zhao J, Muhammad I, Dunbar DC, Khan IA, Fischer NH, Fronczek FR. Three ginkgolide hydrates from Ginkgo biloba L.: ginkgolide A monohydrate, ginkgolide C sesquihydrate and ginkgolide J dihydrate, all determined at 120 K. Acta Crystallogr C. 2002 Mar;58(Pt 3):o195-8. Epub 2002 Feb 28. PubMed PMID: 11870327. 7: Jaracz S, Malik S, Nakanishi K. Isolation of ginkgolides A, B, C, J and bilobalide from G. biloba extracts. Phytochemistry. 2004 Nov;65(21):2897-902. PubMed PMID: 15501258. 8: Ng CC, Duke RK, Hinton T, Johnston GA. GABAA receptor cysteinyl mutants and the ginkgo terpenoid lactones bilobalide and ginkgolides. Eur J Pharmacol. 2016 Apr 15;777:136-46. doi: 10.1016/j.ejphar.2016.03.007. Epub 2016 Mar 4. PubMed PMID: 26953225. 9: Krzek J, Czekaj JS, Rzeszutko W, Ekiert RJ. Validation of capillary gas chromatographic method for determination of bilobalide and ginkgolides A, B, C in Ginkgo biloba dry and liquid extracts. Acta Pol Pharm. 2007 Jul-Aug;64(4):303-10. PubMed PMID: 18536155. 10: Jaracz S, Strømgaard K, Nakanishi K. Ginkgolides: selective acetylations, translactonization, and biological evaluation. J Org Chem. 2002 Jun 28;67(13):4623-6. PubMed PMID: 12076171. 11: Lau AJ, Yang G, Rajaraman G, Baucom CC, Chang TK. Human pregnane X receptor agonism by Ginkgo biloba extract: assessment of the role of individual ginkgolides. J Pharmacol Exp Ther. 2010 Dec;335(3):771-80. doi: 10.1124/jpet.110.172338. Epub 2010 Aug 25. PubMed PMID: 20739453. 12: Scholtyssek H, Damerau W, Wessel R, Schimke I. Antioxidative activity of ginkgolides against superoxide in an aprotic environment. Chem Biol Interact. 1997 Oct 24;106(3):183-90. PubMed PMID: 9413545. 13: Xie J, Ding C, Ge Q, Zhou Z, Zhi X. Simultaneous determination of ginkgolides A, B, C and bilobalide in plasma by LC-MS/MS and its application to the pharmacokinetic study of Ginkgo biloba extract in rats. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Mar 15;864(1-2):87-94. doi: 10.1016/j.jchromb.2008.01.045. Epub 2008 Feb 7. PubMed PMID: 18295555. 14: Jaracz S, Nakanishi K, Jensen AA, Strømgaard K. Ginkgolides and glycine receptors: a structure-activity relationship study. Chemistry. 2004 Mar 19;10(6):1507-18. PubMed PMID: 15034895. 15: Cho HJ, Shon YH, Nam KS. Ginkgolide C inhibits platelet aggregation in cAMP- and cGMP-dependent manner by activating MMP-9. Biol Pharm Bull. 2007 Dec;30(12):2340-4. PubMed PMID: 18057723. 16: Gogös E. Identification and the retention index of bilobalide and ginkgolides using capillary gas chromatography. J Chromatogr Sci. 2002 Oct;40(9):519-22. PubMed PMID: 12433115. 17: Huang SH, Duke RK, Chebib M, Sasaki K, Wada K, Johnston GA. Ginkgolides, diterpene trilactones of Ginkgo biloba, as antagonists at recombinant alpha1beta2gamma2L GABAA receptors. Eur J Pharmacol. 2004 Jun 28;494(2-3):131-8. PubMed PMID: 15212966. 18: Wang Y, Sheng LS, Lou FC. [Analysis and structure identification of trace constituent in the total ginkgolide by using LC/DAD/ESI/MS]. Yao Xue Xue Bao. 2001 Aug;36(8):606-8. Chinese. PubMed PMID: 12579939. 19: Vogensen SB, Strømgaard K, Shindou H, Jaracz S, Suehiro M, Ishii S, Shimizu T, Nakanishi K. Preparation of 7-substituted ginkgolide derivatives: potent platelet activating factor (PAF) receptor antagonists. J Med Chem. 2003 Feb 13;46(4):601-8. PubMed PMID: 12570381. 20: Rui TQ, Zhang L, Qiao HZ, Huang P, Qian S, Li JS, Chen ZP, Fu TM, Di LQ, Cai B. Preparation and Physicochemical and Pharmacokinetic Characterization of Ginkgo Lactone Nanosuspensions for Antiplatelet Aggregation. J Pharm Sci. 2016 Jan;105(1):242-9. doi: 10.1016/j.xphs.2015.10.002. Epub 2015 Dec 22. PubMed PMID: 26852855.