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| | 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;472-15-1 | | Mol File: | 472-15-1.mol |  |
| | 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 | | LogP | 7.653 (est) | | CAS DataBase Reference | 472-15-1(CAS DataBase Reference) |
| Hazard Codes | Xi | | Safety Statements | 24/25 | | WGK Germany | 3 | | HS Code | 29181985 |
| | 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
| | 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 |
| | Betulinic acid Preparation Products And Raw materials |
| Raw materials | betulonic aldehyde | | Preparation Products | Betulin-->(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((tert-butoxycarbonyl)amino)-5 a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate |
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