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B178

Sigma-Aldrich

Butein

solid

Synonym(s):

1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one, 2′,3,4,4′-Tetrahydroxychalcone

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About This Item

Empirical Formula (Hill Notation):
C15H12O5
CAS Number:
487-52-5
Molecular Weight:
272.25
EC Number:
207-659-5
MDL number:
MFCD00017300
UNSPSC Code:
12352200
PubChem Substance ID:
24891611
NACRES:
NA.77

form

solid

color

yellow

solubility

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+

InChI key

AYMYWHCQALZEGT-ORCRQEGFSA-N

Gene Information

rat ... Alox5(25290)

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General description

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 Actions

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.

Features and Benefits

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.

Caution

Photosensitive

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Naghma Khan et al.
Antioxidants & redox signaling, 16(11), 1195-1204 (2011-11-26)
Prostate cancer (PCa) is one of the most common cancers in men in the United States with similar trends worldwide. For several reasons, it is an ideal candidate disease for intervention with dietary botanical antioxidants. Indeed, many botanical antioxidants are
Chia-Yu Ma et al.
Journal of agricultural and food chemistry, 59(16), 9032-9038 (2011-07-21)
Liver cancer is one of the most commonly diagnosed cancers and the leading cause of death in human populations. Butein, a tetrahydroxychalcone, has been shown to induce apoptosis in many human cancer cells, but the effects of butein on the
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
Zafar Rasheed et al.
The Journal of pharmacology and experimental therapeutics, 333(2), 354-363 (2010-02-19)
Activation of mast cells in rheumatoid synovial tissue has often been associated with tumor necrosis factor (TNF)-alpha, interleukin (IL)-6, and IL-8 production and disease pathogenesis by adjacent cell types. Butea monosperma (BM) is a well known medicinal plant in India
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