| Identification | More | [Name]
Betulinic acid | [CAS]
472-15-1 | [Synonyms]
AIRIN
ALS-357
Platanol
Betulinic
Gratiolone
Melaleucin
Ccris 6748
Nsc 113090
Nsc 677578
Lupatic Acid
BETULIC ACID
BETULINIC ACID
Platanolic acid
Einecs 207-448-8
BETULINIC ACID(P)
BETULINIC ACID hplc
Betulinic Acid(98%)
BETULINIC ACID WITH HPLC
BETULINIC ACID, TECH., 90%
Betulinic acid technical grade, 90%
3β-hydroxy-lup-20(29)-ene-28-oicacid
3B-HYDROXY-20(29)-LUPENE-28-OIC ACID
3β-hydroxy-20(29)-lupaene-28-oic acid
3-B-HYDROXY-LUPA-20(30)-ENE 28-OIC ACID
3BETA-HYDROXY-20(29)-LUPENE-28-OIC ACID
3BETA-HYDROXY-20(29)-LUPAENE-28-OIC ACID
(+)-(3β)-3-Hydroxylup-20(29)-en-28-oicacid
LUP-20(29)-EN-28-OIC ACID, 3-HYDROXY-, (3B)-
Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3β)-
Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)-
Lup-20(29)-en-28-oic acid, 3beta-hydroxy-(8ci)
BETULICACID: LUP-20(29)-EN-28-OICACID, 3-HYDROXY-, (3B)-,
(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 | [EINECS(EC#)]
207-448-8 | [Molecular Formula]
C30H48O3 | [MDL Number]
MFCD00009619 | [Molecular Weight]
456.7 | [MOL File]
472-15-1.mol |
| Chemical Properties | Back Directory | [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 ]
neat | [pka]
4.61±0.70(Predicted) | [color ]
White or off-white | [optical activity]
[α]20/D +7.8°, c = 0.9 in pyridine | [Merck ]
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 Information | Back Directory | [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 | [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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