Betulinic AcidA cytotoxic, cell apoptosis causing agent that upregulates caspase-8

Betulinic Acid (CAS 472-15-1)

Betulinic Acid | CAS 472-15-1 is rated 5.0 out of 5 by 1.
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Synonym: 3β-Hydroxy-20(29)-lupaene-28-oic acid
Application: A cytotoxic, cell apoptosis causing agent that upregulates caspase-8
CAS Number: 472-15-1
Molecular Weight: 456.70
Molecular Formula: C30H48O3
* Refer to Certificate of Analysis for lot specific data (including water content).
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Betulinic Acid is a cytotoxic agent isolated from Platanus acerifolia (plane) tree bark. Studies have shown Betulinic Acid, a pentacyclic lupane-type triterpene, to be cytotoxic to leukemia K562 cells. In vitro experiments have shown up-regulation of pro-apoptotic proteins Bax and caspase-3 in mixtures of Betulinic Acid and K562 cells, as well as an increase in NF-κB and reactive oxygen species (ROS). It has been noted that Bax induces cell death by acting on mitochondria via binding of the permeability transition pore complex (PTPC). PTPC is a channel that is involved in permeability regulation of the mitochondrial membrane and this induction of PTPC alone is sufficient to trigger the full apoptosis program of the cell. Additional research has shown that Betulinic Acid acts as a potent inhibitor of Hh/Gli signaling pathway. Betulinic Acid is an activator of Caspase and TGR5.


References

1. Fulda, S., et al. 1998. J. Biol. Chem. 273: 33942-33948. PMID: 9852046
2. Marzo, I., et al. 1998. Science. 281: 2027-2031. PMID: 9748162
3. Chowdhury, A.R., et al. 2002. Med. Sci. Monit. 8: BR254-BR265. PMID: 12118187
4. Qiuling, W., et al. 2010. J. Huazhong Univ. Sci. Technol. Med. Sci. 30: 453-457. PMID: 20714869

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in acetic acid, water (partly miscible), and DMSO.
Storage :
Store at -20° C
Melting Point :
295-298° C (dec.)
Boiling Point :
~550.0° C at 760 mmHg (Predicted)
Density :
~1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.53
Optical Activity :
α20/D +7.8°, c = 0.9 in pyridine
IC50 :
Hh/Gli signaling pathway : IC50 = 32 µM
Ki Data :
SARS coronavirus 3CL protease: Ki= 8200 nM; Clostridium BoNT/A protease light chain: Ki= 14300 nM
pK Values :
pKa: 4.61
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
64971
Merck Index :
14: 1190
MDL Number :
MFCD00009619
EC Number :
207-448-8
SMILES :
CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C(=O)O

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Certificate of Analysis

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Betulinic Acid  Product Citations

See how others have used Betulinic Acid. Click on the entry to view the PubMed entry .

Citations 1 to 1 of 1 total

PMID: # 22365411  Kim, Y. et al. 2012. Eur J Med Chem. 50: 311-8.

Citations 1 to 1 of 1 total

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. This chemical is supplied as a white or off-white powder. Please contact Technical Service if you have further questions concerning this product.
Answered by: Tech Service 9
Date published: 2017-01-18
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Rated 5 out of 5 by from Wu et al Wu et al. (PubMed ID 20714869) found that Betulinic Acid increased the expression of the pro-apoptotic proteins Bax and caspase-3 in K562 cells. -SCBT Publication Review
Date published: 2015-04-06
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