Basic information
- Standard SMILES
O=C(C=Cc1ccc(O)cc1)c1c(O)cc(O)cc1O- InChIKey
YQHMWTPYORBCMF-UHFFFAOYSA-N- Molecular formula
- C15H12O5
- Average molar mass
- 272.25 g/mol
- Monoisotopic mass
- 272.06847348
Names & identifiers
- Preferred name
- 2-Propen-1-one, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-
- IUPAC
- 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
- English name
- NARINGENIN CHALCONE
- Molecular formula
- C15H12O5
- Molecular weight
- 272.25
Names & synonyms
2-Propen-1-one, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-RefChem:1979352',4',6',4-tetrahydroxychalconeSCHEMBL132270orb1221832YQHMWTPYORBCMF-UHFFFAOYSA-NYCA69250AKOS028108638Naringenin chalcone (cis and trans mix)DB-083021NS00015837S9440
Show more names
C06561ISOSALIPURPOLNaringein chalconeNARINGENIN CHALCONE(E)-Naringenin chalcone4,2',4',6'-Tetrahydroxychalconetrans-2'4'6'4-tetrahydroxychalconeNaringenin Chalcone(cis and trans mix)NARINGENIN CHALCONE(cis and trans Mix)(RG)
Q27467486(E/Z)-Naringenin chalcone; Naringenin chalcone (cis and trans mixture); 2',4,4',6'-Tetrahydroxychalcone; Isosalipurpol2 inverted exclamation marka,4,4 inverted exclamation marka,6 inverted exclamation marka-Tetrahydroxychalcone
Database identifiers
- CAS
73692-50-9- PubChem CID
- 155802
- DTXSID
DTXSID201025574
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 98 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 347
Physicochemical properties
- Melting point
- 173 · 173-174℃
- Boiling point
- 538.7 · 538.7±50.0 °C(Predicted)
- Density
- 1.483 · 1.483±0.06 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, protect from light
- solubility
- 15 · DMF:15.0(Max Conc. mg/mL);55.0(Max Conc. mM)DMSO:10.0(Max Conc. mg/mL);36.0(Max Conc. mM)Ethanol:1.0(Max Conc. mg/mL);3.6(Max Conc. mM)
- form
- A solid
- pka
- 6.82 · 6.82±0.40(Predicted)
- color
- Light yellow to orange
- InChI
- InChI=1S/C15H12O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-8,16-17,19-20H
- InChIKey
- YQHMWTPYORBCMF-UHFFFAOYSA-N
- SMILES
- C(C1=C(O)C=C(O)C=C1O)(=O)C=CC1=CC=C(O)C=C1
- LogP
- 2.826 · 2.826 (est)
- FDA UNII
- 6 Z24AS2 · YCF6Z24AS2
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H335-H319-H315
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362-P264-P270-P301+P312-P330-P501
Safety & regulation
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H335-H319-H315
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362-P264-P270-P301+P312-P330-P501
Chemistry & industry
Applications
UsesNaringenin chalcone is an orally active intermediate in flavonol biosynthesis. Naringenin chalcone induces Apoptosis. Naringenin chalcone inhibits the production of MCP-1 and NO. Naringenin chalcone exhibits anticancer activity against glioblastoma. Naringenin chalcone has anti-inflammatory and anti-allergic properties[1][2][3][4][5][6].
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Additional notes
DefinitionChEBI: A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2' ,4, 4', and 6' respectively.
Related reactions
1 records
Linked notes
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