Synonym: (+)-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
CAS Number: 14907-98-3
Empirical Formula (Hill Notation): C26H32O11
Molecular Weight: 520.53
MDL Number: MFCD23726642
Linear Formula: C26H32O11
Product Type: Chemical
| assay |
≥95% (HPLC) |
| biological source |
(Brucia javanica) |
| color |
white to beige |
| form |
powder |
| 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 |
| optical activity |
[α]/D +35 to +44°, c = 0.5 in acetone |
| Quality Level |
100  |
| 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 |
| solubility |
DMSO: 5 mg/mL, clear (warmed) |
| storage condition |
desiccated |
| storage temp. |
−20°C |
| 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. |
| Biochem/physiol Actions: |
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. |
| Packaging: |
5, 25 mg in glass bottle |
| RIDADR |
NONH for all modes of transport |
| WGK Germany |
WGK 3 |
| Flash Point(F) |
Not applicable |
| Flash Point(C) |
Not applicable |
| Purity |
≥95% (HPLC) |
| Storage Temp. |
−20°C |
| UNSPSC |
12352200 |
