butein
(E)-2',3,4,4'-terahydroxychalcone
Identification
| Name | butein |
| IUPAC | (E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one |
| CAS Number | 487-52-5 |
| EINECS | 207-659-5 |
| FDA UNII | 4WVS5M0LGF |
| Molecular Formula | C15 H12 O5 |
| Molecular Weight | 272.25664000 |
| MDL Number | MFCD00017300 |
| Nikkaji Number | J11.660B |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 560.92 °C. @ 760.00 mm Hg (est) |
| Flash Point | 585.00 °F. TCC ( 307.10 °C. ) (est) |
| logP (o/w) | 2.405 (est) |
| Soluble in | water, 481.1 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for butein usage levels up to | not for fragrance use. |
| Recommendation for butein flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
chalcone, 2',3,4,4'-tetrahydroxy-
(2E)-1-(2,4-
dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one
(2E)-1-(2,4-
dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
(E)-1-(2,4-
dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
2-
propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-, (2E)-
(E)-2',3,4,4'-
terahydroxychalcone
2',3,4,4'-
tetrahydroxychalcone
PubMed:
Inhibitory activities of Lignum Sappan extractives on growth and growth-related signaling of tumor cells.
PubMed:
Inhibitory effects of butein on cancer metastasis and bioenergetic modulation.
PubMed:
[Chemical constituents from seeds of Sophora alopecuroides].
PubMed:
Butein, a novel dual inhibitor of MET and EGFR, overcomes gefitinib-resistant lung cancer growth.
PubMed:
The depletion of securin enhances butein-induced apoptosis and tumor inhibition in human colorectal cancer.
PubMed:
Butein suppresses breast cancer growth by reducing a production of intracellular reactive oxygen species.
PubMed:
Inhibition of adipocyte inflammation and macrophage chemotaxis by butein.
PubMed:
Butein induces cell apoptosis and inhibition of cyclooxygenaseâ2 expression in A549 lung cancer cells.
PubMed:
Identification of new natural DNA G-quadruplex binders selected by a structure-based virtual screening approach.
PubMed:
Protective effect of detoxified Rhus verniciflua stokes on human keratinocytes and dermal fibroblasts against oxidative stress and identification of the bioactive phenolics.
PubMed:
Butein Inhibits Angiogenesis of Human Endothelial Progenitor Cells via the Translation Dependent Signaling Pathway.
PubMed:
Cognitive-enhancing effects of Rhus verniciflua bark extract and its active flavonoids with neuroprotective and anti-inflammatory activities.
PubMed:
Butein and its emerging anti-proliferative and pro-apoptotic effects in systemic malignancies.
PubMed:
Butein inhibits NF-κB activation and reduces infiltration of inflammatory cells and apoptosis after spinal cord injury in rats.
PubMed:
Butein is a novel anti-adipogenic compound.
PubMed:
Electrochemical oxidation of butein at glassy carbon electrodes.
PubMed:
Butein protects human dental pulp cells from hydrogen peroxide-induced oxidative toxicity via Nrf2 pathway-dependent heme oxygenase-1 expressions.
PubMed:
Butein imparts free radical scavenging, anti-oxidative and proapoptotic properties in the flower extracts of Butea monosperma.
PubMed:
Inhibitory effect of butein on tumor necrosis factor-α-induced expression of cell adhesion molecules in human lung epithelial cells via inhibition of reactive oxygen species generation, NF-κB activation and Akt phosphorylation.
PubMed:
Butein inhibits the proliferation of breast cancer cells through generation of reactive oxygen species and modulation of ERK and p38 activities.
PubMed:
Butein inhibits ethanol-induced activation of liver stellate cells through TGF-β, NFκB, p38, and JNK signaling pathways and inhibition of oxidative stress.
PubMed:
Natural chalcones as dual inhibitors of HDACs and NF-κB.
PubMed:
Antirestenosis effect of butein in the neointima formation progression.
PubMed:
Butein induces apoptosis in human uveal melanoma cells through mitochondrial apoptosis pathway.
PubMed:
Preparative isolation and purification of neuroprotective compounds from Rhus verniciflua by high speed counter-current chromatography.
PubMed:
Neuroprotective and anti-inflammatory effects of flavonoids isolated from Rhus verniciflua in neuronal HT22 and microglial BV2 cell lines.
PubMed:
Generation of reactive oxygen species mediates butein-induced apoptosis in neuroblastoma cells.
PubMed:
Butein impairs the protumorigenic activity of malignant pleural mesothelioma cells.
PubMed:
Betulin, betulinic acid and butein are inhibitors of acetaldehyde-induced activation of liver stellate cells.
PubMed:
Large enhancement of skeletal muscle cell glucose uptake and suppression of hepatocyte glucose-6-phosphatase activity by weak uncouplers of oxidative phosphorylation.
PubMed:
Butein induces apoptosis and inhibits prostate tumor growth in vitro and in vivo.
PubMed:
Induction of glutathione synthesis and heme oxygenase 1 by the flavonoids butein and phloretin is mediated through the ERK/Nrf2 pathway and protects against oxidative stress.
PubMed:
Butein inhibits the migration and invasion of SK-HEP-1 human hepatocarcinoma cells through suppressing the ERK, JNK, p38, and uPA signaling multiple pathways.
PubMed:
A bHLH transcription factor, DvIVS, is involved in regulation of anthocyanin synthesis in dahlia (Dahlia variabilis).
PubMed:
Inhibitory effects of herbal alkaloids on the tumor necrosis factor-α and nitric oxide production in lipopolysaccharide-stimulated RAW264 macrophages.
PubMed:
HPLC-DAD-MS analysis of dyes identified in textiles from Mount Athos.
PubMed:
Butein from Rhus verniciflua protects pancreatic β cells against cytokine-induced toxicity mediated by inhibition of nitric oxide formation.
PubMed:
The role of chalcones in suppression of NF-κB-mediated inflammation and cancer.
PubMed:
Butein, a tetrahydroxychalcone, suppresses cancer-induced osteoclastogenesis through inhibition of receptor activator of nuclear factor-kappaB ligand signaling.
PubMed:
Suppression of signal transducer and activator of transcription 3 activation by butein inhibits growth of human hepatocellular carcinoma in vivo.
PubMed:
The potential influence of plant polyphenols on the aging process.
PubMed:
Butein downregulates phorbol 12-myristate 13-acetate-induced COX-2 transcriptional activity in cancerous and non-cancerous breast cells.
PubMed:
Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals.
PubMed:
Butein downregulates chemokine receptor CXCR4 expression and function through suppression of NF-κB activation in breast and pancreatic tumor cells.
PubMed:
Butein suppresses the expression of nuclear factor-kappa B-mediated matrix metalloproteinase-9 and vascular endothelial growth factor in prostate cancer cells.
PubMed:
Butein up-regulates the expression of the Ï class of glutathione S-transferase in rat primary hepatocytes through the ERK/AP-1 pathway.
PubMed:
Cloning, functional expression, and characterization of a chalcone 3-hydroxylase from Cosmos sulphureus.
PubMed:
Butein sensitizes human hepatoma cells to TRAIL-induced apoptosis via extracellular signal-regulated kinase/Sp1-dependent DR5 upregulation and NF-kappaB inactivation.
PubMed:
Cotinus coggygria wood: novel flavanone dimer and development of an HPLC/UV/MS method for the simultaneous determination of fourteen phenolic constituents.
PubMed:
Inhibitory effects of polyphenols isolated from Rhus verniciflua on Aldo-keto reductase family 1 B10.
PubMed:
Butrin, isobutrin, and butein from medicinal plant Butea monosperma selectively inhibit nuclear factor-kappaB in activated human mast cells: suppression of tumor necrosis factor-alpha, interleukin (IL)-6, and IL-8.
PubMed:
Chalcones enhance TRAIL-induced apoptosis in prostate cancer cells.
PubMed:
[Chalcones from Bauhinia glauca subsp. pernervosa].
PubMed:
[Studies on phenolic compounds from Sophora alopecuroides].
PubMed:
Activation of SIRT1 by resveratrol represses transcription of the gene for the cytosolic form of phosphoenolpyruvate carboxykinase (GTP) by deacetylating hepatic nuclear factor 4alpha.
PubMed:
Butein induces G(2)/M phase arrest and apoptosis in human hepatoma cancer cells through ROS generation.
PubMed:
Selective cytotoxic effects on human cancer cell lines of phenolic-rich ethyl-acetate fraction from Rhus verniciflua Stokes.
PubMed:
Butein suppresses c-Myc-dependent transcription and Akt-dependent phosphorylation of hTERT in human leukemia cells.
PubMed:
Phytochemical analysis of young fustic (Cotinus coggygria heartwood) and identification of isolated colourants in historical textiles.
PubMed:
Bioactive flavonoids of the flowers of Butea monosperma.
PubMed:
Butein suppresses constitutive and inducible signal transducer and activator of transcription (STAT) 3 activation and STAT3-regulated gene products through the induction of a protein tyrosine phosphatase SHP-1.
PubMed:
Butein sensitizes human leukemia cells to apoptosis induced by tumor necrosis factor-related apoptosis inducing ligand (TRAIL).
PubMed:
Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts.
PubMed:
A novel anticancer effect of butein: inhibition of invasion through the ERK1/2 and NF-kappa B signaling pathways in bladder cancer cells.
PubMed:
Antimicrobial and antioxidative activities of bioactive constituents from Hydnophytum formicarum Jack.
PubMed:
Nuclear factor-kappaB-dependent reversal of aging-induced alterations in T cell cytokines.
PubMed:
Structural requirements of 2',4',6'-tris(methoxymethoxy) chalcone derivatives for anti-inflammatory activity: the importance of a 2'-hydroxy moiety.
PubMed:
In vitro metabolism of isoliquiritigenin by human liver microsomes.
PubMed:
Butein blocks tumor necrosis factor alpha-induced interleukin 8 and matrix metalloproteinase 7 production by inhibiting p38 kinase and osteopontin mediated signaling events in HT-29 cells.
PubMed:
Flavonoid inhibitors as novel antimycobacterial agents targeting Rv0636, a putative dehydratase enzyme involved in Mycobacterium tuberculosis fatty acid synthase II.
PubMed:
Butein suppresses bile acid-induced hepatocyte apoptosis through a JNK-dependent but ERK-independent pathway.
PubMed:
Butein, a tetrahydroxychalcone, inhibits nuclear factor (NF)-kappaB and NF-kappaB-regulated gene expression through direct inhibition of IkappaBalpha kinase beta on cysteine 179 residue.
PubMed:
The small polyphenolic molecule kaempferol increases cellular energy expenditure and thyroid hormone activation.
PubMed:
Green tea catechins potentiate triclosan binding to enoyl-ACP reductase from Plasmodium falciparum (PfENR).
PubMed:
Pathway engineering for healthy phytochemicals leading to the production of novel flavonoids in tomato fruit.
PubMed:
Phenolic-rich fraction from Rhus verniciflua Stokes (RVS) suppress inflammatory response via NF-kappaB and JNK pathway in lipopolysaccharide-induced RAW 264.7 macrophages.
PubMed:
2',4',6'-Tris(methoxymethoxy) chalcone attenuates hepatic stellate cell proliferation by a heme oxygenase-dependent pathway.
PubMed:
Rhus verniciflua stokes extract: radical scavenging activities and protective effects on H2O2-induced cytotoxicity in macrophage RAW 264.7 cell lines.
PubMed:
Biocatalytic synthesis of butein and sulfuretin by Aspergillus alliaceus.
PubMed:
Anti-platelet effects of bioactive compounds isolated from the bark of Rhus verniciflua Stokes.
PubMed:
Flavonoids purified from Rhus verniciflua Stokes actively inhibit cell growth and induce apoptosis in human osteosarcoma cells.
PubMed:
Are tyrosine kinases involved in mediating contraction-stimulated muscle glucose transport?
PubMed:
The plant polyphenol butein inhibits testosterone-induced proliferation in breast cancer cells expressing aromatase.
PubMed:
The chalcone butein from Rhus verniciflua Stokes inhibits clonogenic growth of human breast cancer cells co-cultured with fibroblasts.
PubMed:
Chalcones as potent tyrosinase inhibitors: the importance of a 2,4-substituted resorcinol moiety.
PubMed:
Facilitation of the purinergic contractile response of the guinea pig vas deferens by sodium orthovanadate.
PubMed:
Inhibition of lipopolysaccharide-induced expression of inducible nitric oxide synthase by butein in RAW 264.7 cells.
PubMed:
Cyclooxygenase inhibitory flavonoids from the stem bark of Semecarpus anacardium Linn.
PubMed:
Extract from Rhus verniciflua Stokes is capable of inhibiting the growth of human lymphoma cells.
PubMed:
Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers.
PubMed:
Relationship between flavonoid structure and inhibition of farnesyl protein transferase.
PubMed:
First bacterial chalcone isomerase isolated from Eubacterium ramulus.
PubMed:
Butein ameliorates renal concentrating ability in cisplatin-induced acute renal failure in rats.
PubMed:
Determination of butein in rat serum by high performance liquid chromatography.
PubMed:
The chalcone butein from Rhus verniciflua shows antifibrogenic activity.
PubMed:
Inhibitory effects of several flavonoids on E-selectin expression on human umbilical vein endothelial cells stimulated by tumor necrosis factor-alpha.
PubMed:
Application of a molecularly imprinted polymer for the effective recognition of different anti-epidermal growth factor receptor inhibitors.
PubMed:
[Studies on flavonoid constituents of Caragana intermediia].
PubMed:
Hypotensive effect of butein via the inhibition of angiotensin converting enzyme.
PubMed:
Selective separation of active inhibitors of epidermal growth factor receptor from Caragana jubata by molecularly imprinted solid-phase extraction.
PubMed:
Butein suppresses myofibroblastic differentiation of rat hepatic stellate cells in primary culture.
PubMed:
Conjugation of chlorambucil with GSH by GST purified from human colon adenocarcinoma cells and its inhibition by plant polyphenols.
PubMed:
Identification of Rhus verniciflua Stokes compounds that exhibit free radical scavenging and anti-apoptotic properties.
PubMed:
Inhibition of epidermal growth factor receptor tyrosine kinase by chalcone derivatives.
PubMed:
Butein, a plant polyphenol, induces apoptosis concomitant with increased caspase-3 activity, decreased Bcl-2 expression and increased Bax expression in HL-60 cells.
PubMed:
Synthesis of flavonoids and their effects on aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues.
PubMed:
Flavonoids inhibit cell growth and induce apoptosis in B16 melanoma 4A5 cells.
PubMed:
Inhibitory activity of flavonoids and tannins against HIV-1 protease.
PubMed:
Antioxidant properties of butein isolated from Dalbergia odorifera.
PubMed:
Butein, a specific protein tyrosine kinase inhibitor.
PubMed:
Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera.
PubMed:
Inhibition of glutathione reductase by plant polyphenols.
PubMed:
Glutathione conjugation of chlorambucil: measurement and modulation by plant polyphenols.
PubMed:
Inhibition of various isoforms of rat liver glutathione S-transferases by tannic acid and butein.
PubMed:
Butein (3,4,2',4'-tetrahydroxychalcone) ameliorates experimental anti-glomerular basement membrane antibody-associated glomerulonephritis (3).
PubMed:
Inhibition of the efflux of glutathione S-conjugates by plant polyphenols.
PubMed:
Butein ameliorates experimental anti-glomerular basement membrane (GBM) antibody-associated glomerulonephritis in rats (1).
PubMed:
Endothelium-dependent relaxation of rat aorta by butein, a novel cyclic AMP-specific phosphodiesterase inhibitor.
PubMed:
Variation in the modulation of superoxide-induced single-strand breaks in plasmid pBR322 DNA by biological antioxidants.
PubMed:
Cytotoxic effect of butein on human colon adenocarcinoma cell proliferation.
PubMed:
Inhibitory effects of plant polyphenols on rat liver glutathione S-transferases.
PubMed:
Protective effects of hydroxychalcones on free radical-induced cell damage.
PubMed:
Effects of gamma-linolenic acid, flavonoids, and vitamins on cytotoxicity and lipid peroxidation.
PubMed:
Studies on lipid oxidation in fish phospholipid liposomes.
PubMed:
Effects of flavonoids on cyclic AMP phosphodiesterase and lipid mobilization in rat adipocytes.
PubMed:
Cytotoxic effect of plant polyphenols and fat-soluble vitamins on malignant human cultured cells.
PubMed:
Effect of myricetin and other flavonoids on the liver plasma membrane Ca2+ pump. Kinetics and structure-function relationships.
PubMed:
Phytoalexin synthesis in soybean cells: elicitor induction of reductase involved in biosynthesis of 6'-deoxychalcone.
PubMed:
Inhibition of 12-O-tetradecanoylphorbol-13-acetate-mediated epidermal ornithine decarboxylase induction and skin tumor promotion by new lipoxygenase inhibitors lacking protein kinase C inhibitory effects.
PubMed:
Metabolism and excretion of butein, 2',3,4-trihydroxychalcone, 3-O-methylbutein, 4-O-methylbutein and 2',4',4-trihydroxychalcone in the rat.
PubMed:
Condensed tannins. 10. Isolation of (--)-butin and butein from wattle heartwoods.