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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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
Dong-Oh Moon et al.
Molecular cancer therapeutics, 9(6), 1583-1595 (2010-06-03)
Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) induces cell death in various types of cancer cells but has little or no effect on normal cells. Human hepatoma cells are resistant to TRAIL-induced apoptosis. Although butein is known to mediate anticancer, anti-inflammatory
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
N Y Kim et al.
Pharmacology & toxicology, 88(5), 261-266 (2001-06-08)
In the present study we have investigated whether butein could induce apoptosis in human leukaemic HL-60 cells. The treatment of HL-60 cells with butein induced apoptotic cell death as determined by morphological and biochemical changes. Apoptotic DNA fragments in the
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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