Ginkgolide C (BN-52022) is a naturally occuring product isolated from Ginko and a GABA-A receptor, α-1 GlyR, and PAF receptor antagonist. It suppresses production of TxA2 to inhibit platelet aggregation and inhibits formation of superoxide and hydroxyl radicals.

Physicochemical Properties

Molecular Formula	C20H24O11
Molecular Weight	440.4
Exact Mass	440.131
CAS #	15291-76-6
Related CAS #	15291-76-6
PubChem CID	9867869
Appearance	White to off-white solid powder
Density	1.7±0.1 g/cm3
Boiling Point	813.8±65.0 °C at 760 mmHg
Melting Point	>3000ºC
Flash Point	291.4±27.8 °C
Vapour Pressure	0.0±6.6 mmHg at 25°C
Index of Refraction	1.671
LogP	0.16
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	1
Heavy Atom Count	31
Complexity	957
Defined Atom Stereocenter Count	12
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
InChi Key	AMOGMTLMADGEOQ-DTDWCABLSA-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: C[C@@H]1C(O[C@H]2[C@@H]([C@]34[C@@H]5OC([C@@]3([C@@]12O)O[C@@H]6OC([C@@H]([C@]46[C@H](C(C)(C)C)[C@H]5O)O)=O)=O)O)=O
Chemical Name	Ginkgolide A, 1,7-dihydroxy-, (1alpha,7beta)-
Synonyms	BN-52022; BN52022; BN 52022; Ginkgolide C
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	After a 24-hour treatment, 3T3-L1 cells' adipogenesis was inhibited by ginkgolide C (3-100 μM), but its viability was unaffected. When compared to the control group, ginkgolide C (10-100 μM) dramatically reduced lipid accumulation and increased glycerol release in 3T3-L1 adipocytes. In differentiated 3T3-L1 adipocytes, ginkgolide C inhibits the expression of PPAR-α and PPAR-γ and decreases the expression of C/EBPα, C/EBPβ, and SREBP-1c. Furthermore, in differentiated 3T3-L1 adipocytes, Ginkgolide C (3-100 μM) dose-dependently inhibits the expression of mRNA and adipogenesis-related proteins (FAS, LPL, and aP2). Additionally, in a concentration-dependent manner, ginkgolide C (3-100 μM) increases the phosphorylation of AMPKα and ACC-1 and significantly promotes the production of Sirt1 [1]. In a dose-dependent manner, ginkgolide C (1, 10, 50, 100, and 500 mM) dramatically inhibited the rat platelet aggregation induced by collagen (10 mg/mL). In collagen-stimulated platelets, ginkgolide C (50, 100 mM) induces the formation of activated MMP-9 (86 kDa) from MMP-9 precursor (92 kDa) [2].
References	[1]. Ginkgolide C Suppresses Adipogenesis in 3T3-L1 Adipocytes via the AMPK Signaling Pathway. Evid Based Complement Alternat Med. 2015;2015:298635. [2]. Ginkgolide C inhibits platelet aggregation in cAMP- and cGMP-dependent manner by activating MMP-9. Biol Pharm Bull. 2007 Dec;30(12):2340-4.
Additional Infomation	ginkgolide-C has been reported in Ginkgo biloba with data available. See also: Ginkgo (part of).

Solubility Data

Solubility (In Vitro)

DMSO : ~250 mg/mL (~567.67 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.68 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.68 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (5.68 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.2707 mL	11.3533 mL	22.7066 mL
	5 mM	0.4541 mL	2.2707 mL	4.5413 mL
	10 mM	0.2271 mL	1.1353 mL	2.2707 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.