1-(4-Hydroxyphenyl)-3-phenylprop-2-en-1-one

HCID 94240CAS 2657-25-2

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Grundinformationen

Standard-SMILES: O=C(C=Cc1ccccc1)c1ccc(O)cc1
InChIKey: UAHGNXFYLAJDIN-UHFFFAOYSA-N
Summenformel: C15H12O2
Durchschnittliche Molmasse: 224,25 g/mol
Monoisotopische Masse: 224,08372962

Namen und Bezeichner

Bevorzugter Name: 1-(4-Hydroxyphenyl)-3-phenylprop-2-en-1-one
IUPAC: 1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one
Englischer Name: 4'-Hydroxychalcone
Summenformel: C15H12O2
Molmasse: 224.25

Namen und Synonyme

1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-oneMFCD000164844-CinnamoylphenolSPECTRUM200407BIDD:ER00831-(4-Hydroxyphenyl)-3-phenyl-2-propenal(E)-1-(4-Hydroxy-phenyl)-3-phenyl-propenoneSpectrum_000721Spectrum2_000203Spectrum3_000175Spectrum4_001607KBioGR_001953

Weitere Namen anzeigen

4'-HydroxychalconeHYDROXYCHALCONE, 4'-4'-Hydroxychalcone98%4'-Hydroxychalcone>4'-Hydroxychalcone 98%4'-Hydroxychalcone,97%4’-Hydroxychalcone-97%HYDROXYCHALCONE, 4-(RG)4'-Hydroxychalcone, ≥ 95.0%2-BENZAL-4'-HYDROXYACETOPHENONE

KBioSS_001201SCHEMBL127606SPBio_000185KBio2_001201KBio2_003769KBio2_006337KBio3_001169UAHGNXFYLAJDIN-UHFFFAOYSA-N

Datenbank-Bezeichner

CAS: 2657-25-2
PubChem CID: 94240
DTXSID: DTXSID8022458

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,7
Polarare Oberfläche (TPSA): 37,3 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 3
Schwere Atome: 17
Formalladung: 0
Komplexität: 269

Physikochemische Eigenschaften

Schmelzpunkt: 174 · 174-178 °C
Siedepunkt: 419.6 · 419.6±45.0 °C(Predicted)
Dichte: 1.191 · 1.191±0.06 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
Löslichkeit: 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS (pH 7.2) (1:4): 0.2 mg/ml
Aggregatzustand: powder to crystal
pka: 7.72 · 7.72±0.15(Predicted)
Farbe: Light orange to Yellow to Green
BRN: 2049150 · 2049150
InChI: InChI=1S/C15H12O2/c16-14-9-7-13(8-10-14)15(17)11-6-12-4-2-1-3-5-12/h1-11,16H
InChIKey: UAHGNXFYLAJDIN-IZZDOVSWSA-N
SMILES: C(C1=CC=C(O)C=C1)(=O)C=CC1=CC=CC=C1
LogP: 3.65 · 3.650 (est)
CAS Datenbank: 2657 · 2657-25-2(CAS DataBase Reference)

Sicherheit und Regulatorisches

Sicherheitsdaten

hs_code: 29145090
risk_code: 36/37/38
hazard_code: Xi
safety_code: 37/39-26-37

Chemie und Industrie

Anwendungen · 2 Einträge

Beschreibung4''-hydroxy Chalcone is a chalcone metabolite with diverse biological activities. It is formed when chalcone is metabolized by the cytochrome (CYP) P450 isoform CYP1A1 or CYP2C6. 4''-hydroxy Chalcone is estrogenic in MCF-7 cells and is cytotoxic at concentrations higher than 100 nM. It inhibits TNF-α-induced NF-κB signaling and the trypsin-, chymotrypsin-, and caspase-like proteolytic activities of the 26S proteasome in K562 cells in a dose-dependent manner. 4''-hydroxy Chalcone reduces growth of K562, U937, and Jurkat cancer cell lines in a dose-dependent manner without effecting viability of peripheral blood mononuclear cells (PBMCs). It also inhibits glutathione reductase (GSH-RD; IC50 = 47.3 μM) in vitro in a reversible and non-competitive manner.

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