2'-hydroxychalcone

2-propen-1-one, 1-(2-hydroxyphenyl)-3-phenyl-

CAS: 1214-47-7 C15 H12 O2 MW: 224.25904000

Identification

Name2'-hydroxychalcone
IUPAC(E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
CAS Number1214-47-7
EINECS214-928-0
FDA UNIIVY06DZ94OC
Molecular FormulaC15 H12 O2
Molecular Weight224.25904000
MDL NumberMFCD00016441
Nikkaji NumberJ133.569C
Beilstein0976324

Regulatory

Physical Properties

Food Chemicals Codex Listed No
Boiling Point 396.60 °C. @ 760.00 mm Hg (est)
Flash Point 337.00 °F. TCC ( 169.40 °C. ) (est)
logP (o/w) 4.000 (est)
Soluble in water, 52.14 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityunreported-mammal (species unspecified) LD50 620 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for 2'-hydroxychalcone usage levels up tonot for fragrance use.
Recommendation for 2'-hydroxychalcone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

acrylophenone, 2'-hydroxy-3-phenyl- chalcone, 2'-hydroxy- (8CI) 2'- hydroxy-3-phenyl acrylophenone (E)-2'- hydroxychalcone o- hydroxychalcone 1-(2- hydroxyphenyl)-3-phenyl-2-propen-1-one (E)-1-(2- hydroxyphenyl)-3-phenylprop-2-en-1-one 2- propen-1-one, 1-(2-hydroxyphenyl)-3-phenyl- PubMed: Cytotoxic activity of substituted chalcones in terms of molecular electronic properties. PubMed: SAR studies of o-hydroxychalcones and their cyclized analogs and study them as novel inhibitors of cathepsin B and cathepsin H. PubMed: Discovery of 2'-hydroxychalcones as autophagy inducer in A549 lung cancer cells. PubMed: AgOTf-catalyzed reactions of naphthols/substituted phenols with 2-hydroxychalcones: facile synthesis of di-aromatic ring-fused [3.3.1]bicyclic compounds. PubMed: Theoretical study on the antioxidant properties of 2'-hydroxychalcones: H-atom vs. electron transfer mechanism. PubMed: Regiospecificity of human UDP-glucuronosyltransferase isoforms in chalcone and flavanone glucuronidation determined by metal complexation and tandem mass spectrometry. PubMed: Impact of water on the cis-trans photoisomerization of hydroxychalcones. PubMed: 1H and 13C NMR spectral assignments of 2'-hydroxychalcones. PubMed: 2-Hydroxychalcone and xanthohumol inhibit invasion of triple negative breast cancer cells. PubMed: Solution-processed bulk heterojunction solar cells based on BF(2)-hydroxychalcone complexes. PubMed: Dynamic residual complexity of the isoliquiritigenin-liquiritigenin interconversion during bioassay. PubMed: [Synthesis of structural fragments of natural flavonoids and flavolignans from 2'-hydroxychalcones]. PubMed: Efficient NIR-light emission from solid-state complexes of boron difluoride with 2'-hydroxychalcone derivatives. PubMed: A synthetic chalcone as a potent inducer of glutathione biosynthesis. PubMed: Solid-phase synthesis of 2'-hydroxychalcones. Effects on cell growth inhibition, cell cycle and apoptosis of human tumor cell lines. PubMed: PPARα activation by culinary herbs and spices. PubMed: Fluorinated 2'-hydroxychalcones as garcinol analogs with enhanced antioxidant and anticancer activities. PubMed: Synthesis of stilbene-fused 2'-hydroxychalcones and flavanones. PubMed: Silver nanoparticle-catalyzed Diels-Alder cycloadditions of 2'-hydroxychalcones. PubMed: Mulberry Diels-Alder adducts: synthesis of chalcomoracin and mulberrofuran C methyl ethers. PubMed: Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties. PubMed: Structural characterization of nitrated 2'-hydroxychalcones by electrospray ionization tandem mass spectrometry. PubMed: Inhibitory activity of prostaglandin E2 production by the synthetic 2'-hydroxychalcone analogues: Synthesis and SAR study. PubMed: Electron transfer-initiated Diels-Alder cycloadditions of 2'-hydroxychalcones. PubMed: High-performance liquid chromatography separation of enantiomers of flavanone and 2'-hydroxychalcone under reversed-phase conditions. PubMed: Microwave-assisted reaction of 2'-hydroxychalcones with hydrazides to synthesize flavanone hydrazone and 4,5-dihydropyrazole derivatives. PubMed: Synthesis and PPAR-gamma ligand-binding activity of the new series of 2'-hydroxychalcone and thiazolidinedione derivatives. PubMed: Heme oxygenase-1 mediates the anti-inflammatory actions of 2'-hydroxychalcone in RAW 264.7 murine macrophages. PubMed: VT 1H NMR investigations of resonance-assisted intramolecular hydrogen bonding in 4-(dimethylamino)-2'-hydroxychalcone. PubMed: The plant polyphenol butein inhibits testosterone-induced proliferation in breast cancer cells expressing aromatase. PubMed: Hydroxychalcones exhibit differential effects on XRE transactivation. PubMed: Differential activation of heme oxygenase-1 by chalcones and rosolic acid in endothelial cells. PubMed: Inhibition of lipopolysaccharide-induced expression of inducible nitric oxide synthase and tumor necrosis factor-alpha by 2'-hydroxychalcone derivatives in RAW 264.7 cells. PubMed: Diprenylated chalcones and other constituents from the twigs of Dorstenia barteri var. subtriangularis. PubMed: Inhibition of peroxynitrite-mediated LDL oxidation by prenylated flavonoids: the alpha,beta-unsaturated keto functionality of 2'-hydroxychalcones as a novel antioxidant pharmacophore. PubMed: Mechanistic approach to the cyclization reaction of a 2'-hydroxychalcone analogue with light and solvent. PubMed: Conjugation of chlorambucil with GSH by GST purified from human colon adenocarcinoma cells and its inhibition by plant polyphenols. PubMed: Efficient liquid-phase synthesis of 2'-hydroxychalcones. PubMed: Chalcones: structural requirements for antioxidant, estrogenic and antiproliferative activities. PubMed: Inhibition of prostalglandin E2 production by 2'-hydoxychalcone derivatives and the mechanism of action. PubMed: The (1)H NMR chemical shift for the hydroxy proton of 4-(dimethylamino)-2'-hydroxychalcone in chloroform: a theoretical approach to its inverse dependence on the temperature. PubMed: Inhibitory effects of 2'-hydroxychalcones on rat lens aldose reductase and rat platelet aggregation. PubMed: 2'-hydroxychalcone inhibits nuclear factor-kappaB and blocks tumor necrosis factor-alpha- and lipopolysaccharide-induced adhesion of neutrophils to human umbilical vein endothelial cells. PubMed: Growth inhibition of oral bacteria related to denture stomatitis by anti-candidal chalcones. PubMed: Glutathione conjugation of chlorambucil: measurement and modulation by plant polyphenols. PubMed: Inhibition of the efflux of glutathione S-conjugates by plant polyphenols. PubMed: Chemoprevention of 4-nitroquinoline 1-oxide-induced rat oral carcinogenesis by the dietary flavonoids chalcone, 2-hydroxychalcone, and quercetin. PubMed: Synthesis and pharmacological evaluation of 2'-hydroxychalcones and flavones as inhibitors of inflammatory mediators generation. PubMed: Cytotoxic effect of butein on human colon adenocarcinoma cell proliferation. PubMed: Inhibition of ocular inflammation by chalcone derivatives and prednisolone. PubMed: [Kinetics of the bacteriostatic activity of natural and synthetic chalcones on a strain of Staphylococcus aureus]. PubMed: [Reactions concerned in tertiary amine n-oxides. VI. Reactions of 2'-hydroxychalcone derivatives with amine N-oxides (author's transl)]. PubMed: 2'-hydroxychalcone as an analytical reagent for beryllium. PubMed: [2'-hydroxychalcone and 3-hydroxyflavone sulfonic acid derivatives (author's transl)]. PubMed: [Synthetic studies on chalcone-flavanone groups. IV. Ultraviolet absorption spectra of 2',4'-dihydroxychalcone, 4'-(benzyloxy)-2'-hydroxychalcone, and their pyridine analogs].