2-hydroxychalcone
2-propen-1-one, 3-(2-hydroxyphenyl)-1-phenyl-
Identification
| Name | 2-hydroxychalcone |
| IUPAC | (E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one |
| CAS Number | 644-78-0 |
| EINECS | 211-422-1 |
| FDA UNII | Search |
| Molecular Formula | C15 H12 O2 |
| Molecular Weight | 224.25904000 |
| MDL Number | MFCD00016449 |
| Nikkaji Number | J95.421G |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Flash Point | 32.00 °F. TCC ( 0.00 °C. ) (est) |
| Soluble in | water, 240.3 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 2-hydroxychalcone usage levels up to | not for fragrance use. |
| Recommendation for 2-hydroxychalcone flavor usage levels up to | not for flavor use. |
Potential Uses
Natural Occurrence
Synonyms
2-
hydroxybenzylidene acetophenone
3-(2-
hydroxyphenyl)-1-phenyl-2-propen-1-one
(E)-3-(2-
hydroxyphenyl)-1-phenylprop-2-en-1-one
2-
propen-1-one, 3-(2-hydroxyphenyl)-1-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 functionalized 2-aryl-4-(indol-3-yl)-4H-chromenes via iodine-catalyzed domino Michael addition-intramolecular cyclization reaction.
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:
Synthesis and Antimicrobial Activity of Some New 2-(3-(4-Aryl)-1-phenyl-1H-pyrazol-4-yl) Chroman-4-ones.
PubMed:
Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
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:
Size-controlled deposition of Ag nanoparticles on alumina with the assistance of a photo-induced chromic reaction, and study of their catalytic properties.
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:
Gas-phase nazarov cyclization of protonated 2-methoxy and 2-hydroxychalcone: an example of intramolecular proton-transport catalysis.
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:
Synthesis and antifungal activity of some new 3-hydroxy-2-(1-phenyl-3-aryl-4-pyrazolyl) chromones.
PubMed:
Dehydrozingerone, chalcone, and isoeugenol analogues as in vitro anticancer agents.
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:
Total synthesis of anthocyanidins via Heck reaction.
PubMed:
VT 1H NMR investigations of resonance-assisted intramolecular hydrogen bonding in 4-(dimethylamino)-2'-hydroxychalcone.
PubMed:
Metabolism of the alpha,beta-unsaturated ketones, chalcone and trans-4-phenyl-3-buten-2-one, by rat liver microsomes and estrogenic activity of the metabolites.
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:
Chemoprotective potentials of homoisoflavonoids and chalcones of Dracaena cinnabari: modulations of drug-metabolizing enzymes and antioxidant activity.
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 of isoflavones].
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].