2-Hydroxychalcone

2-Hydroxychalcone Basic information
Product Name:2-Hydroxychalcone
Synonyms:BENZYLIDENE-2-HYDROXYACETOPHENONE;(E)-3-(2-HYDROXYPHENYL)-1-PHENYLPROP-2-EN-1-ONE;HYDROXYCHALCONE, 2-;2-HYDROXYCHALCONE;2-HYDROXYBENZYLIDENE ACETOPHENONE;2-(2-HYDROXYBENZAL)ACETOPHENONE;2-(2-HYDROXYBENZYLIDENE)ACETOPHENONE;(2-Hydroxybenzylidene)acetophenone~3-(2-Hydroxyphenyl)-1-phenyl-2-propen-1-one
CAS:644-78-0
MF:C15H12O2
MW:224.25
EINECS:211-422-1
Product Categories:Biochemistry;Building Blocks for Liquid Crystals;Chalcones;Chalcones, etc. (Building Blocks for Liquid Crystals);Flavonoids;Functional Materials
Mol File:644-78-0.mol
2-Hydroxychalcone Structure
2-Hydroxychalcone Chemical Properties
Melting point 144-150 °C(lit.)
Boiling point 396.3±34.0 °C(Predicted)
density 1.191±0.06 g/cm3(Predicted)
form powder
pka9.26±0.35(Predicted)
color Yellow
BRN 2049134
CAS DataBase Reference644-78-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
HS Code 29147000
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
2-Hydroxychalcone Usage And Synthesis
Description2-hydroxychalcone, a natural flavonoid, is a potent antioxidant, inhibiting lipid peroxidation. It is also capable of inducing apoptosis by downregulating Bcl-2 levels and inhibiting the activation of NF-kB.
SynthesisA synthesis of 2-Hydroxychalcone was conducted using acetophenone and o-hydroxybenzaldehyde as starting materials. The reaction was catalyzed by potassium hydroxide and ethanol was used as the solvent.
in vitro2-Hydroxychalcone inhibits invasion of triple negative breast cancer cells.
2-hydroxychalcone inhibits the adhesion of peripheral neutrophils to the endothelial cell monolayers by inhibiting the expression of ICAM-1, VCAM-1, and E-selectin in a concentration-dependent manner.
References[1]. Sun Young Kim, et al. 2-Hydroxychalcone and Xanthohumol Inhibit Invasion of Triple Negative Breast Cancer Cells. Chem Biol Interact. 2013 May 25;203(3):565-72. DOI:10.1016/j.cbi.2013.03.012
[2]. B Madan, et al. 2'-hydroxychalcone Inhibits Nuclear factor-kappaB and Blocks Tumor Necrosis Factor-Alpha- And Lipopolysaccharide-Induced Adhesion of Neutrophils to Human Umbilical Vein Endothelial Cells. Mol Pharmacol. 2000 Sep;58(3):526-34. DOI:10.1124/MOL.58.3.526
[3]. Sonochemical Synthesis of 2’-Hydroxy-Chalcone Derivatives with Potential Anti-Oomycete Activity doi: 10.3390/antibiotics9090576
2-Hydroxychalcone Preparation Products And Raw materials
Raw materialsEthanol-->Potassium hydroxide-->Salicylaldehyde-->Acetophenone
DIMETHOXY-2'-HYDROXYCHALCONE, 2,3-(RG) 4Hydroxy-4-HydroxyChalcone HYDROXYCHALCONE, 4-,4-HYDROXYCHALCONE 5'-BROMO-3,4-DIMETHOXY-2'-HYDROXYCHALCONE DIMETHOXY-2'-HYDROXYCHALCONE, 2,4-,2,4-DIMETHOXY-2'-HYDROXYCHALCONE 5'-BROMO-4-CHLORO-2'-HYDROXYCHALCONE 4-HYDROXYCHALCONE, (4-HYDROXYBENZYLIDENE- ACETOPHENONE (E)-2'-hydroxychalcone 4-BUTYL-4'-HYDROXYCHALCONE DIMETHOXY-2'-HYDROXYCHALCONE, 2,4-(RG) 4,5'-DIMETHOXY-2'-HYDROXYCHALCONE HYDROXYCHALCONE, 2-,TRANS-2-HYDROXYCHALCONE 4',6'-DIMETHOXY-2'-HYDROXYCHALCONE,DIMETHOXY-2'-HYDROXYCHALCONE, 4',6'- 3-Chloro-3HydroxyChalcone 4',6'-DIMETHOXY-4-FLUORO-2'-HYDROXYCHALCONE 5'-(dimethylamino)-2'-hydroxychalcone hydrochloride 2Hydroxy-4-HydroxyChalcone 4,6'-DIMETHOXY-2'-HYDROXYCHALCONE

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