Betulinic acid, CAS No. 472-15-1

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472-15-1

Catalog No. EBD2184748

CAS 472-15-1

Name Betulinic acid

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Basic Information

Synonyms: Betulinicacid CCRIS6748 Mairin NSC113090 NSC677578 3-Hydroxylup-20(29)-en-28-oicacid Lup-20(29)-en-28-oicacid,3-hydroxy-,(3beta)- Lup-20(29)-en-28-oicacid,3beta-hydroxy- (3beta)-3-hydroxylup-20(29)-en-28-oicacid (3beta,5xi,9xi,13xi,18xi)-3-hydroxylup-20(29)-en-28-oicacid (1R,3aS,5bS,9R,11aR,13aS)-9-hydroxy-5b,8,8,11a-tetramethyl-1-(1-methylethenyl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylicacid

Molecular Formula: C30H48O3

Molecular Weight: 456.7

MDL Number: MFCD00009619

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Phytochemicals and Natural Products Medicinal Chemistry > APIs and Their Salts > Antineoplastic Agents

Product Description:

Betulinic acid is a pentacyclic lupane-type triterpenoid naturally found in the bark of white birch trees (*Betula* species) and other plants. It is structurally characterized by a lupane skeleton with a carboxylic acid group at the C-17 position. This compound is a white to off-white crystalline powder with limited solubility in water but good solubility in organic solvents like DMSO and ethanol. Its primary and most extensively researched application is in the field of oncology. Betulinic acid exhibits selective cytotoxicity against a variety of human cancer cell lines, including melanoma, neuroblastoma, glioblastoma, and leukemia, while showing relatively low toxicity to normal cells. The proposed mechanisms of action include the induction of apoptosis through the mitochondrial pathway, inhibition of topoisomerase I, and anti-angiogenic effects. Due to its potent and selective antitumor activity, it is widely studied as a promising natural product-derived lead compound for the development of novel anticancer drugs (APIs). Beyond its direct anticancer potential, betulinic acid also demonstrates significant anti-inflammatory, anti-HIV, and hepatoprotective properties. It serves as a crucial reference standard and a key starting material for the semi-synthesis of more potent derivatives. Its safety profile is generally favorable, though comprehensive toxicological data for human use are still under investigation in clinical trials.

Physical Properties

Melting Point: 295-298 °C (dec.)(lit.)

Boiling Point: 550 °C at 760 mmHg

Flash Point: 300.5 °C

Density: 1.065 g/cm3

Refractivity: 7.8 ° (C=0.9, Pyridine)

Storage: 2-8°C

Analytical Data

Appearance: powder