Betulinic acid Chemical Properties

Melting point:

295-298 °C (dec.) (lit.)

alpha 

D25 +7.5° (c = 0.37 in pyridine)

Boiling point:

550.0±33.0 °C(Predicted)

Density 

1.065±0.06 g/cm3(Predicted)

refractive index 

7.8 ° (C=0.9, Pyridine)

storage temp. 

2-8°C

solubility 

Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).

form 

Solid

pka

4.61±0.70(Predicted)

color 

White or off-white

optical activity

[α]20/D +7.8°, c = 0.9 in pyridine

Merck 

14,1190

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.

InChIKey

QGJZLNKBHJESQX-FZFNOLFKSA-N

LogP

7.653 (est)

CAS DataBase Reference

472-15-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29181985

MSDS

• Language:English Provider:SigmaAldrich

Betulinic acid Usage And Synthesis

Description

Betulinic acid (472-15-1) is a natural Lupane triterpenoid from white birch tree (Betula pubescens). Induces apoptosis in a variety of cell lines.1 Induces mitochondrial permeability transition pore opening.2 ?Acts as a chemosensitizer for anticancer drug treatment in chemoresistant colon cancer cell lines.3 Cell permeable.

Chemical Properties

colorless Needles

Uses

antineoplastic

Uses

Betulinic acid (BetA) has been used:

• to test its effects as an antiviral agent against Dengue virus (DENV)
• as a sterol regulatory element-binding protein (SREBP) inhibitor to repress the lipid metabolism and proliferation of clear cell renal cell carcinoma (ccRCC) cells
• as a treatment to test its anti-tumor properties for cell viability and apoptotic cell death assays in multiple myeloma models

Uses

Betulinic Acid is a natural pentacyclic triterpenoid. Betulinic Acid displays anti-inflammatory and anti-HIV activity. Betulinic Acid selectively induces apoptosis in tumor cells by directly activati ng the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism. Betulinic Acid also exhibits TGR5 agonist activity

Definition

ChEBI: A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium cla iflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties.

General Description

Betulinic acid is a lupane-type triterpene, which can be prepared from betulin via oxidation using chromium oxide (VI). Along with anti-HIV-1 and anti-tumor activity, it also shows other bioactivities such as anti-inflammatory, antibacterial, in vitro antimalarial, anthelmintic and antioxidant activities.

Biological Activity

Natural triterpenoid that displays anti-HIV and antitumor activity. Induces the production of reactive oxygen species (ROS) and activates NF- κ B. Exhibits TRG5 agonist activity (EC 50 = 1.04 μ M).

Biochem/physiol Actions

Betulinic acid, a pentacyclic triterpene, selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism.

Anticancer Research

This compound is a pentacyclic triterpene obtained from Betula and Zizyphus species,which shows selective cytotoxicity against human melanoma cells (Shoeb2006). It generates reactive oxygen species, activates MAPK cascade, inhibitstopoisomerase I, inhibits angiogenesis, modulates pro-growth transcriptionalactivators, modulates the activity of aminopeptidase-N, and thereby inducesapoptosis in cancer cells (Desai et al. 2008; Fulda 2008).

storage

+4°C

References

1) Ehrhardt et al. (2004) Betulinic acid-induced apoptosis in leukemia cells; Leukemia, 18 1406 2) Mullauer et al. (2009) Betulinic acid induces cytochrome c release and apoptosis in Bax/Bak-independent, permeability transition pore dependent fashion.; Apoptosis, 14 191 3) Jung et al. (2007) Effect of betulinic acid on anticancer drug-resistant colon cancer cells; Basic Clin. Pharmacol. Toxicol., 101 277

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