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Merck

B178

Sigma-Aldrich

Butein

solid

Synonym(e):

(2E)- 1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-on, 2′,3,4,4′-Tetrahydroxychalkon

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About This Item

Empirische Formel (Hill-System):
C15H12O5
CAS-Nummer:
Molekulargewicht:
272.25
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:
NACRES:
NA.77

Form

solid

Farbe

yellow

Löslichkeit

DMSO: >50 mg/mL
H2O: insoluble

SMILES String

OC1=CC(O)=C(C(/C=C/C2=CC(O)=C(O)C=C2)=O)C=C1

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+

InChIKey

AYMYWHCQALZEGT-ORCRQEGFSA-N

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Allgemeine Beschreibung

Butein (2′,3,4,4′-tetrahydroxychalcone) is a chalcone and a flavonoid, that is produced in plants. It is a plant polyphenol and a bioactive constituent, that is extracted from the heartwood of Dalbergia odorifera, Caragana jubata and Rhus verniciflua stokes, and the stem bark of cashews (Semecarpus anacardium).

Biochem./physiol. Wirkung

Butein exhibit several pharmacological activities, such as anti-oxidant and anti-inflammatory activity. It stimulates apoptotic cell death of human cervical cancer cells. It has therapeutic potentials for chronic diseases, including liver tuberculosis, obesity, diabetes and hypertension. Butein can repress migration and invasion of bladder, breast and pancreatic cancer cells.
Inhibits EGFR and Src tyrosine kinase activities; inhibits cAMP-dependent PDE-IV. Induces apoptosis in B16 melanoma cells and HL-60 human leukemia cells.

Leistungsmerkmale und Vorteile

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Vorsicht

Photosensitive

Lagerklassenschlüssel

13 - Non Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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Butein induces apoptotic cell death of human cervical cancer cells
Yang P Y, et al.
Oncology Letters, 16(5), 6615-6623 (2018)
Agnieszka Szuster-Ciesielska et al.
Journal of gastroenterology, 48(2), 222-237 (2012-06-23)
Butein has been reported to prevent and partly reverse liver fibrosis in vivo; however, the mechanisms of its action are poorly understood. We, therefore, aimed to determine the antifibrotic potential of butein. We assessed the influence of the incubation of
Dong-Oh Moon et al.
Toxicology in vitro : an international journal published in association with BIBRA, 24(7), 1927-1934 (2010-08-11)
3,4,2',4'-Tetrahydroxychalcone (butein) has potent anti-inflammatory, anti-cancer and anti-fibrogenic effects. However, little is known about the mechanism by which butein inhibits metastasis and invasion. This study aimed to investigate the effects of butein on the expression of matrix metalloproteinase (MMP-9) and
Karin Schlangen et al.
Journal of experimental botany, 61(12), 3451-3459 (2010-06-23)
A chalcone 3-hydroxylase (CH3H) cDNA clone was isolated and characterized from Cosmos sulphureus petals accumulating butein (2',3,4,4'-tetrahydroxychalcone) derivatives as yellow flower pigments. The recombinant protein catalyses the introduction of an additional hydroxyl group in the B-ring of chalcones, a reaction
S M Yu et al.
European journal of pharmacology, 280(1), 69-77 (1995-06-23)
Butein, isolated from Dalbergia odorifera T. Chen, caused endothelium-dependent relaxation of rat aorta precontracted with phenylephrine. This effect was abolished in endothelium-denuded aorta and in endothelium-intact aorta in the presence of NG-monomethyl-L-arginine, oxyhemoglobin and methylene blue, whereas the effect was

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