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butein
(E)-2',3,4,4'-terahydroxychalcone

Supplier Sponsors

Name:(E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
CAS Number: 487-52-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-659-5
FDA UNII: 4WVS5M0LGF
Nikkaji Web:J11.660B
MDL:MFCD00017300
XlogP3-AA:2.80 (est)
Molecular Weight:272.25664000
Formula:C15 H12 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Butein 98%
BOC Sciences
For experimental / research use only.
Butein >98%
Odor: characteristic
Use: Butein, a plant polyphenol isolated from Rhus verniciflua, is able to inhibit the activation of protein tyrosine kinase, NF-?B and STAT3, also inhibits EGFR. The use of these compounds in the treatment of breast cancer
Carbosynth
For experimental / research use only.
Butein
Coompo
For experimental / research use only.
Butein from Plants ≥96%
EMD Millipore
For experimental / research use only.
Butein
sds
ExtraSynthese
For experimental / research use only.
Butein (HPLC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
Butein ≥95%
Sigma-Aldrich: Sigma
For experimental / research use only.
Butein solid
sds
TCI AMERICA
For experimental / research use only.
Butein >98.0%(HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281222
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
Chemidplus:0000487525
 
References:
 (E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281222
Pubchem (sid):135023805
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C08578
HMDB (The Human Metabolome Database):Search
FooDB:FDB000082
Export Tariff Code:2914.50.3000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 bean fava bean fruit
Search Trop Picture
 
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
 

Articles:

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 cyclooxygenase‑2 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 π 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.
 
Notes:
None found
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