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

HCID 94240

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Basic information

CAS: 2657-25-2
Standard SMILES: O=C(C=Cc1ccccc1)c1ccc(O)cc1
InChIKey: UAHGNXFYLAJDIN-UHFFFAOYSA-N
Molecular formula: C15H12O2
Average molar mass: 224.25 g/mol
Monoisotopic mass: 224.08372962

Names & identifiers

Preferred name: 1-(4-Hydroxyphenyl)-3-phenylprop-2-en-1-one
IUPAC: 1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one
English name: 4'-Hydroxychalcone
Molecular formula: C15H12O2
Molecular weight: 224.25

Names & synonyms

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

Show more names

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

Database identifiers

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

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 37.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 17
Formal charge: 0
Complexity: 269

Physicochemical properties

Melting point: 174 · 174-178 °C
Boiling point: 419.6 · 419.6±45.0 °C(Predicted)
Density: 1.191 · 1.191±0.06 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
solubility: 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
form: powder to crystal
pka: 7.72 · 7.72±0.15(Predicted)
color: 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 DataBase Reference: 2657 · 2657-25-2(CAS DataBase Reference)
FDA UNII: 2 K338K8UOA · 2K338K8UOA
UNSPSC Code: 12352200 · 12352200
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 37 · 37/39-26-37
HS Code: 29145090 · 29145090

Safety & regulation

Safety data

hs_code: 29145090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 37/39-26-37
Hazard statements: H315-H319-H335
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Chemistry & industry

Applications · 3 items

Description4''-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.

Usesantineoplastic,

Uses4''-Hydroxychalcone is a chalone derivative that exhibits moderate to good antiviral activity against tobacco mosaic virus (TMV).