855057

Betulinic acid

technical grade, 90%

• 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
• EC Number: 207-448-8
• MDL number: MFCD00009619
• UNSPSC Code: 85151701
• PubChem Substance ID: 24888370
• NACRES: NA.22

Properties

• grade: technical grade
• Quality Level: 100
• assay: 90%
• form: powder
• optical activity: [α]20/D +7.8°, c = 0.9 in pyridine
• mp: 295-298 °C (dec.) (lit.)
• functional group: carboxylic acid; hydroxyl
• 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 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.

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)