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Ginkgolic acid

Alias: AK46666 AK-46666 Ginkgoic acid
Cat No.:V21590 Purity: ≥98%
Ginkgolic Acid is a natural compound that can inhibit SUMOylation in in vitro experiments with IC50 of 3.0 μM.
Ginkgolic acid
Ginkgolic acid Chemical Structure CAS No.: 22910-60-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
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25mg
50mg
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Other Forms of Ginkgolic acid:

  • Ginkgoneolic acid
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Ginkgolic Acid is a natural compound that can inhibit SUMOylation in in vitro experiments with IC50 of 3.0 μM.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
In vitro, ginkgo acid has an IC50 value of 3.0 μM, which inhibits the SUMOylation of RanGAP1-C2. Treatment with ginkgo acid markedly lowered SUMOylated p53 levels. Crucially, ubiquitination of proteins in cells is unaffected by ginkgolic acid. In a dose-dependent way, ginkgo acid prevents E1 from binding to GA-BODIPY [1]. Concentration-dependently, ginkgolic acid (31.2 μg/mL) can inhibit HIV protease activity by 60% when compared to the negative control. Using 50 and 100 μg/mL of ginkgo acid can successfully prevent HIV infection in human peripheral blood monoclonal cells. At concentrations up to 150 μg/mL, ginkgo acid does not significantly harm Jurkat cells [2]. Only in a dose- and time-dependent manner did GA suppress the growth of tumorigenic cell lines. 70.53±4.54% of Hep-2 and 63.5±7.2% of Tca8113 cells were arrested in the GO/G1 phase after being treated with GA for 72 hours. The corresponding apoptosis percentages were 40.4±1.58 and 38.4±1.7%, respectively. The expression of anti-apoptotic Bcl-2 protein is downregulated and pro-apoptotic Bax protein is upregulated when activated caspase-3 is treated with GA. This ultimately results in a decrease in the Bcl-2/Bax ratio of tumor cells in human PBMC cells. At concentrations up to 150 μg/mL, ginkgo acid does not significantly harm Jurkat cells [3].
References

[1]. Ginkgolic acid inhibits protein SUMOylation by blocking formation of the E1-SUMO intermediate. Chem Biol. 2009 Feb 27;16(2):133-40.

[2]. Ginkgolic acid inhibits HIV protease activity and HIV infection in vitro. Med Sci Monit. 2012 Aug;18(8):BR293-298.

[3]. Antitumor effects of ginkgolic acid in human cancer cell occur via cell cycle arrest and decrease the Bcl-2/Bax ratio to induce apoptosis. Chemotherapy. 2010;56(5):393-402.

[4]. Pharmacological inhibition of SUMO-1 with ginkgolic acid alleviates cardiac fibrosis induced by myocardial infarction in mice. Toxicol Appl Pharmacol. 2018 Apr 15;345:1-9.

Additional Infomation
Ginkgoic acid is a hydroxybenzoic acid. It is functionally related to a salicylic acid.
Ginkgolic acid has been reported in Myrcia multiflora, Ozoroa insignis, and other organisms with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H34O3
Molecular Weight
346.51
Exact Mass
346.25
CAS #
22910-60-7
Related CAS #
Ginkgolic Acid (C13:0);20261-38-5
PubChem CID
5281858
Appearance
White to off-white solid powder
Density
1.0±0.1 g/cm3
Boiling Point
492.1±40.0 °C at 760 mmHg
Melting Point
136-137ºC
Flash Point
265.5±23.8 °C
Vapour Pressure
0.0±1.3 mmHg at 25°C
Index of Refraction
1.527
LogP
9.44
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
14
Heavy Atom Count
25
Complexity
364
Defined Atom Stereocenter Count
0
SMILES
CCCCCC/C=C\CCCCCCCC1=C(C(=CC=C1)O)C(=O)O
InChi Key
YXHVCZZLWZYHSA-FPLPWBNLSA-N
InChi Code
InChI=1S/C22H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h7-8,15,17-18,23H,2-6,9-14,16H2,1H3,(H,24,25)/b8-7-
Chemical Name
2-hydroxy-6-[(Z)-pentadec-8-enyl]benzoic acid
Synonyms
AK46666 AK-46666 Ginkgoic acid
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~288.60 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.75 mg/mL (7.94 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 27.5 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: ≥ 2.75 mg/mL (7.94 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 27.5 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 2.8859 mL 14.4296 mL 28.8592 mL
5 mM 0.5772 mL 2.8859 mL 5.7718 mL
10 mM 0.2886 mL 1.4430 mL 2.8859 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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