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Merck

203987

Butein

A cell-permeable, reversible, substrate competitive, plant polyphenol that acts as a specific protein tyrosine kinase inhibitor.

Synonym(s):

Butein, 2ʹ,4ʹ,3,4-Tetrahydroxychalcone

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About This Item

Empirical Formula (Hill Notation):
C15H12O5
CAS Number:
487-52-5
Molecular Weight:
272.25
UNSPSC Code:
12352200
MDL number:
MFCD00017300
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze, protect from light

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InChI

1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+

InChI key

AYMYWHCQALZEGT-ORCRQEGFSA-N

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

yellow

solubility

DMSO: 10 mg/mL, methanol: soluble

shipped in

ambient

storage temp.

−20°C

Quality Level

100

General description

A cell-permeable, reversible, substrate competitive, plant polyphenol that acts as a specific protein tyrosine kinase inhibitor. Potently inhibits the tyrosine kinase activity of the EGF receptor (IC50 = 65 µM) and p60c-src (IC50 = 65 µM) The inhibition is competitive with respect to ATP and non-competitive with respect to the substrate. Butein is also a potent antioxidant and anti-inflammatory agent. Has been shown to inhibit glutathione reductase (GSH-RD) and rat liver glutathione S-transferase (GST; IC50 = 9 µM). Reported to activate sirtuins and promote the survival of eukaryotic cells.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Tyrosine kinase activity of the EGF receptor
Product competes with ATP.
Reversible: yes
Target IC50: 65 µM against tyrosine kinase activity of the EGF receptor

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 weeks at -20°C.

Other Notes

Howitz, K.T., et al. 2003. Nature425, 191.
Chan, S.C., et al. 1998. Planta Med.64, 153.
Yang, E.B., et al. 1998. Biochem. Biophys. Res. Commun. 245, 435.
Zhang, K., et al. 1997. Biochem. Pharmacol. 54, 1047.
Zhang, K., and Das, N.P. 1994. Biochem. Pharmacol. 47, 2063.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

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’.

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