Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

SML1868

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C26H32O11
CAS Number:
14907-98-3
Molecular Weight:
520.53
MDL number:
MFCD23726642
UNSPSC Code:
12352200
NACRES:
NA.77

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Steffan Vartanian et al.
Molecular & cellular proteomics : MCP, 15(4), 1220-1231 (2015-12-30)
The KEAP1/Nrf2 pathway senses and responds to changes in intracellular oxidative stress. Mutations that result in constitutive activation of Nrf2 are present in several human tumors, especially non-small cell lung cancer. Therefore, compounds that inhibit Nrf2 activity might be beneficial
Katsuya Iuchi et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 125, 109928-109928 (2020-02-01)
An increasing number of metal-based compounds, including arsenic trioxide, auranofin, and cisplatin, have been reported to have antitumor activity. Their beneficial effects are controlled by a transcription factor, nuclear factor (erythroid-derived 2)-like 2 (NRF2). In response to oxidative stress, NRF2
Guangqin Zhu et al.
Hereditas, 159(1), 21-21 (2022-05-14)
Ferroptosis, a novel manner of cell death depended on iron ion, contributed to goat mammary epithelial cell dysfunction. Interleukin-6 (IL-6) is a major pro-inflammatory factor during many inflammation-related diseases including mastitis, and a quite recently identified ferroptosis inducer. This study
W Willingham et al.
Biochimica et biophysica acta, 654(2), 169-174 (1981-07-27)
The mechanism by which brusatol inhibits protein synthesis in rabbit reticulocytes has been investigated. When added to reticulocyte lysates, brusatol inhibits endogenous protein synthesis only after a lag of 2-4 min at 30 degrees C. During this period 80 S
Shakeel Mir et al.
Breast cancer research : BCR, 24(1), 48-48 (2022-07-15)
A pro-oxidant enzyme, NADPH oxidase 4 (Nox4) has been reported to be a critical downstream effector of TGFβ-induced myofibroblast transformation during fibrosis. While there are a small number of studies suggesting an oncogenic role of Nox4 derived from activated fibroblasts
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service