| Betulinic acid Basic information |
| Product Name: |
Betulinic acid |
| Synonyms: |
Betulinic acid technical grade, 90%;3BETA-HYDROXY-20(29)-LUPENE-28-OIC ACID;3BETA-HYDROXY-20(29)-LUPAENE-28-OIC ACID;3B-HYDROXY-20(29)-LUPENE-28-OIC ACID;(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentaMethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid;Birch bark extract/β-Amyrin/betulinic acid;3-B-HYDROXY-LUPA-20(30)-ENE 28-OIC ACID;BETULINIC ACID |
| CAS: |
472-15-1 |
| MF: |
C30H48O3 |
| MW: |
456.71 |
| EINECS: |
207-448-8 |
| Product Categories: |
Tri-Terpenoids;sy;Pentacyclic Triterpenes;chemical reagent;Inhibitors;Triterpenoids;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Antineoplastic;natural product |
| Mol File: |
472-15-1.mol |
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| 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). |
| pka |
4.61±0.70(Predicted) |
| form |
neat |
| 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 |
| CAS DataBase Reference |
472-15-1(CAS DataBase Reference) |
| Hazard Codes |
Xi |
| Safety Statements |
24/25 |
| WGK Germany |
3 |
| HS Code |
29181985 |
| Provider |
Language |
| SigmaAldrich |
English |
| |
| 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 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 |
| 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
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| 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.
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| 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). |
| 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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| Betulinic acid Preparation Products And Raw materials |
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