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Submit ReviewBetulinic acid
Description: Antitumor and anti-HIV agent; activates NF-κB. Also TGR5 agonist
Chemical Name: (+)-(3β)-3-Hydroxylup-20(29)-en-28-oic acid
Biological Activity for Betulinic acid
Betulinic acid is a natural triterpenoid that displays anti-HIV and antitumor activity. Induces the production of reactive oxygen species (ROS) and activates NF-κB. Also a GPBA receptor partial agonist (EC50 = 1.04 μM, efficacy 83%). Betulinic acid suppresses areobic glycolysis by regulating the Cav-1/NF-κB/c-Myc pathway in and inhibits growth in breast cancer cells.
Technical Data for Betulinic acid
| M. Wt | 456.7 |
| Formula | C30H48O3 |
| Storage | Store at +4°C |
| CAS Number | 472-15-1 |
| PubChem ID | 64971 |
| InChI Key | QGJZLNKBHJESQX-FZFNOLFKSA-N |
| Smiles | O[C@H]1CC[C@@]2(C)[C@](CC[C@]3(C)[C@@]([H])2CC[C@@]4([H])[C@](C)3CC[C@]5([C@](O)=O)[C@@]([H])4[C@H]([C@@](C)=C)CC5)([H])C(C)1C |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Betulinic acid
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 22.84 | 50 |
Preparing Stock Solutions for Betulinic acid
The following data is based on the product molecular weight 456.7. 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.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.5 mM | 4.38 mL | 21.9 mL | 43.79 mL |
| 2.5 mM | 0.88 mL | 4.38 mL | 8.76 mL |
| 5 mM | 0.44 mL | 2.19 mL | 4.38 mL |
| 25 mM | 0.09 mL | 0.44 mL | 0.88 mL |
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Product Datasheets for Betulinic acid
References for Betulinic acid
References are publications that support the biological activity of the product.
Kashiwada et al (1996) Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents. J.Med.Chem. 39 1016 PMID: 8676334
Fulda (2008) Betulinic acid for cancer treatment and prevention. Int.J.Mol.Sci. 9 1096 PMID: 19325847
Genet et al (2010) Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: potential impact in diabetes. J.Med.Chem. 53 178 PMID: 19911773
Jiao et al (2019) Betulinic acid suppresses breast cancer aerobic glycolysis via caveolin-1/NF-?B/c-Myc pathway. Biochem.Pharmacol. 161 149 PMID: 30684465
If you know of a relevant reference for Betulinic acid, please let us know.
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Keywords: Betulinic acid, Betulinic acid supplier, antitumor, anti-HIV, NFkappaB, NF-kB, NFκB, TGR5, receptors, activators, activates, apoptosis, inducers, partial, agonists, agonism, Cav-1, c-Myc, Apoptosis, Inducers, NF-kB/IkB, GPBA, Receptors, 3906, Tocris Bioscience
2 Citations for Betulinic acid
Citations are publications that use Tocris products. Selected citations for Betulinic acid include:
Qing et al (2022) MTAP loss correlates with an immunosuppressive profile in GBM and its substrate MTA stimulates alternative macrophage polarization. Sci Rep 12 4183 PMID: 35264604
Inoue et al (2012) Dipeptidyl peptidase IV inhibition potentiates amino acid- and bile acid-induced bicarbonate secretion in rat duodenum. Neurotox Res 303 G810 PMID: 22821947
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Programmed Cell Death Poster
There are two currently recognized forms of programmed cell death: apoptosis and necroptosis. This poster summarizes the signaling pathways involved in apoptosis, necroptosis and cell survival following death receptor activation, and highlights the influence of the molecular switch, cFLIP, on cell fate.
Pathways for Betulinic acid
