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Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 560.92 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 585.00 °F. TCC ( 307.10 °C. ) (est)
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| logP (o/w): | 2.405 (est) |
| Soluble in: |
| | water, 481.1 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | natural substances and extractives |
| Recommendation for butein usage levels up to: | | | not for fragrance use.
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| Recommendation for butein flavor usage levels up to: |
| | not for flavor use.
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Safety References:
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:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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. |
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