B8936

Betulinic acid

≥98% (HPLC)

• Synonym(s): 3β-Hydroxy-20(29)-lupaene-28-oic acid, Lupatic acid, Mairin
• Empirical Formula (Hill Notation): C₃₀H₄₈O₃
• CAS Number: 472-15-1
• Molecular Weight: 456.70
• NACRES: NA.25
• PubChem Substance ID: 329773146
• UNSPSC Code: 12352205
• EC Number: 207-448-8
• MDL number: MFCD00009619

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• mp: 295-298 °C (dec.) (lit.)
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: 2-8°C
• SMILES string: CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O
• InChI: 1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
• InChI key: QGJZLNKBHJESQX-FZFNOLFKSA-N

Description

General description

Betulinic acid (BetA) is a natural product mostly sourced from the birch tree (Betula spp.). This pentacyclic lupanetype triterpenoid is also associated with other species such as Syzygium spp., Diospyros spp., Ziziphus spp., and Paeonia spp..

Application

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

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.

Betulinic acid displays many biological and pharmacological properties such as anticancer, anti-inflammatory, anti-bacterial, anti-human immunodeficiency virus (HIV), and anti-malarial properties.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable