B178
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:
Molecular Weight:
272.25
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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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).[1]
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.[1]
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 Code
13 - Non Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
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
E B Yang et al.
Biochemical and biophysical research communications, 245(2), 435-438 (1998-05-08)
Butein, a plant polyphenol, was shown to be a specific protein tyrosine kinase inhibitor. This compound inhibited not only the epidermal growth factor (EGF)-stimulated auto-phosphotyrosine level of EGF receptor in HepG2 cells but also tyrosine-specific protein kinase activities of EGF
E Aizu et al.
Carcinogenesis, 7(11), 1809-1812 (1986-11-01)
Both 2,3,5-trimethyl-6-(12-hydroxy-5,10-dodecadiynyl)-1,4-benzoquinone (AA861) and 3,4,2',4'-tetrahydroxychalcone inhibited 12-lipoxygenase of mouse epidermis. The IC50 of AA861 and 3,4,2',4'-tetrahydroxychalcone for epidermal 12-lipoxygenase were 1.9 and 0.2 microM, respectively. These agents showed very weak inhibitory actions on epidermal cyclooxygenase, with the potency of inhibition
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