SML1868

Brusatol

≥95% (HPLC)

• Synonym(s): (+)-Brusatol, (11β,12α,15β)-13,20-Epoxy-3,11,12-trihydroxy-15-[(3-methyl-1-oxo-2-buten-1-yl)oxy]-2,16-dioxo-picras-3-en-21-oic acid methyl ester, Brutasol, NSC 172924, Yatansin
• Empirical Formula (Hill Notation): C₂₆H₃₂O₁₁
• CAS Number: 14907-98-3
• Molecular Weight: 520.53
• MDL number: MFCD23726642
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• biological source: (Brucia javanica)
• Quality Level: 100
• assay: ≥95% (HPLC)
• form: powder
• optical activity: [α]/D +35 to +44°, c = 0.5 in acetone
• storage condition: desiccated
• color: white to beige
• solubility: DMSO: 5 mg/mL, clear (warmed)
• storage temp.: −20°C
• SMILES string: CC1=C(O)C(C[C@@]2(C)[C@@]1([H])C[C@]3([H])[C@]45[C@]2([H])[C@@H](O)[C@H](O)[C@](OC5)(C(OC)=O)[C@]4([H])[C@@H](OC(C=C(C)C)=O)C(O3)=O)=O
• InChI: 1S/C26H32O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h6,12,14,17-21,29-31H,7-9H2,1-5H3/t12-,14+,17+,18+,19+,20+,21-,24-,25+,26-/m0/s1
• InChI key: ZZZYHIMVKOHVIH-VILODJCFSA-N

Description

Application

Brusatol has been used to study the protective role of Nrf2 (nuclear factor, erythroid 2 like 2 ) in intestinal ischemia/reperfusion induced injury.

Biochem/physiol Actions

Brusatol (Brutasol) is a plant-derived natural quassinoid that exhibits broad cytotoxicity in cancer cultures (IC₅₀ <1 μM against 457 cancer cell lines) by inhibiting de novo synthesis of cellular proteins (Effective conc. <50 nM in A549 cells), including NRF2.

Brusatol promotes Nrf2 (nuclear factor, erythroid 2 like 2 ) ubiquitination and degradation. Brusatol upregulates the expression of multiple ribosomal components and controls macromolecular complex function.

Safety Information

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