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Ursonic acid

Cat No.:V29870 Purity: ≥98%
Ursonic acid is a naturally occurring triterpene acid that can cause apoptosis in human cancer/tumor cells through multiple signaling pathways.
Ursonic acid
Ursonic acid Chemical Structure CAS No.: 6246-46-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Ursonic acid is a naturally occurring triterpene acid that can cause apoptosis in human cancer/tumor cells through multiple signaling pathways.
Ursonic acid (CAS#: 6246-46-4), also known as 3-ketoursolic acid, is a pentacyclic triterpenoid with pharmacological activities including anti-inflammatory, antioxidant, and anticancer properties. It is a naturally occurring triterpenoid that induces apoptosis of human cancer cells through multiple signaling pathways. The compound has potential applications in the treatment of inflammatory diseases, metabolic disorders, and cancer. Its molecular formula is C30H46O3 with a molecular weight of 454.68 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Ursonic acid targets multiple pathways involved in inflammation, cancer, and metabolism. It inhibits migration and invasion of human osteosarcoma cells through suppression of mitogen-activated protein kinases and matrix metalloproteinases. The compound exerts anti-diabetic effects through anti-glycating properties and by inhibiting PTP1B and activating the PI3K/Akt signaling pathway in insulin-resistant cells. It is a potential HIV-1 protease inhibitor.
ln Vitro
In vitro, Ursonic acid inhibits migration and invasion of human osteosarcoma cells through suppression of MAPKs and MMPs. It exerts anti-diabetic effects by inhibiting PTP1B and activating PI3K/Akt signaling in insulin-resistant C2C12 cells. The compound induces apoptosis of human cancer cells through multiple signaling pathways. It shows antiviral activity against Herpes simplex virus types I and II in vitro.
ln Vivo
In vivo, Ursonic acid has potential applications in the treatment of inflammatory diseases, metabolic disorders, and cancer. It can be used in depression treatment medicine. The compound induces apoptosis of human cancer cells through multiple signaling pathways. Its anti-diabetic, anti-inflammatory, and anticancer effects have been demonstrated in preclinical studies. Further in vivo studies are ongoing to fully characterize its therapeutic potential.
Enzyme Assay
In vitro enzyme assays for Ursonic acid involve measuring PTP1B inhibition. PTP1B activity is assessed using suitable substrates, and the compound is added at varying concentrations. IC50 values are calculated from dose-response curves. PI3K/Akt pathway activation is assessed by measuring phosphorylation of Akt. MMP activity is measured using gelatin zymography. MAPK activity is assessed by Western blot. Anti-HIV activity is assessed by measuring HIV-1 protease inhibition.
Cell Assay
In vitro cell-based assays for Ursonic acid are conducted in cancer cell lines, osteosarcoma cells, and insulin-resistant C2C12 cells. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with the compound at varying concentrations. Cell viability is assessed by MTT or CCK-8 assays. Apoptosis is evaluated by Annexin V/PI staining. Migration and invasion are assessed using Transwell assays. PTP1B activity and PI3K/Akt signaling are assessed by Western blot. Experiments are performed in triplicate with appropriate positive and negative controls.
Animal Protocol
Ursonic acid in vivo studies are conducted in animal models of cancer, inflammation, and diabetes. Animals are treated with Ursonic acid via oral administration or injection. Tumor growth is monitored by caliper measurements. For anti-inflammatory studies, inflammatory markers are measured. For anti-diabetic studies, blood glucose and insulin levels are measured. Animals are monitored for clinical signs. Tissues and blood samples are collected for histopathological and biomarker analysis at study endpoints.
ADME/Pharmacokinetics
Ursonic acid (MW 454.68 g/mol, C30H46O3) is a pentacyclic triterpenoid. It is also known as 3-ketoursolic acid. The compound is soluble in chloroform, dichloromethane, ethyl acetate, DMSO, and acetone. It is stable under recommended storage conditions. Pharmacokinetic parameters such as half-life, bioavailability, and tissue distribution would be determined in species-specific studies. Ursonic acid is used in anti-inflammatory, anticancer, and anti-diabetic research.
Toxicity/Toxicokinetics
Ursonic acid is generally well-tolerated in preclinical studies. The compound is a natural triterpenoid with established safety profiles. Its anti-inflammatory, antioxidant, anticancer, and anti-diabetic activities have been demonstrated with acceptable safety profiles. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard safety precautions should be followed when handling. Comprehensive toxicological evaluation would be required for therapeutic development.
References

[1]. Gai, L., Cai, N., Wang, L., Xu, X. & Kong, X. Ursolic acid induces apoptosis via Akt/NF-kappaB signaling suppression in T24 human bladder cancer cells. Molecular medicine reports 7, 1673-1677, doi:10.3892/mmr.2013.1364 (2013).

[2]. Manu, K. A. & Kuttan, G. Ursolic acid induces apoptosis by activating p53 and caspase-3 gene expressions and suppressing NF-kappaB mediated activation of bcl-2 in B16F-10 melanoma cells. International immunopharmacology 8, 974-981, doi:10.1016/j.intimp.2008.02.013 (2008).

[3]. Protective effect of ursolic acid on ethanol-mediated experimental liver damage in rats. Life Sci. 2006 Jan 11;78(7):713-8.

Additional Infomation
Ursonic acid is a triterpenoid compound. It has been reported to be found in Salvia splendens, Olex arvensis, and other organisms with relevant data.
Ursonic acid (3-Ketoursolic acid) is a pentacyclic triterpenoid with anti-inflammatory, antioxidant, and anticancer properties. It inhibits osteosarcoma cell migration/invasion via MAPK and MMP suppression, exerts anti-diabetic effects via PTP1B inhibition and PI3K/Akt activation, and is a potential HIV-1 protease inhibitor. Its molecular formula is C30H46O3 with a molecular weight of 454.68 g/mol. All applications are limited to non-human research use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H46O3
Molecular Weight
454.6844
Exact Mass
454.344
CAS #
6246-46-4
PubChem CID
9890209
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
555.1±50.0 °C at 760 mmHg
Melting Point
283 °C(dec.)
Flash Point
303.6±26.6 °C
Vapour Pressure
0.0±3.2 mmHg at 25°C
Index of Refraction
1.550
LogP
8.43
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Heavy Atom Count
33
Complexity
916
Defined Atom Stereocenter Count
9
SMILES
C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCC(=O)C5(C)C)C)C)[C@@H]2[C@H]1C)C)C(=O)O
InChi Key
MUCRYNWJQNHDJH-OADIDDRXSA-N
InChi Code
InChI=1S/C30H46O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-22,24H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,24+,27+,28-,29-,30+/m1/s1
Chemical Name
(1S,2R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,5,6,6a,7,8,8a,11,12,13,14b-tetradecahydropicene-4a-carboxylic 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 : ~50 mg/mL (~109.97 mM)
H2O : ~1 mg/mL (~2.20 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.50 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 (5.50 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 2.1993 mL 10.9967 mL 21.9935 mL
5 mM 0.4399 mL 2.1993 mL 4.3987 mL
10 mM 0.2199 mL 1.0997 mL 2.1993 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

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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?
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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:
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  • 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
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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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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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