Naringenin chalcone

Naringenin chalcone is a common chalconoid (or chalcone, not to be confused with the compound chalcone). It is synthesized from 4-coumaroyl-CoA and malonyl-CoA by chalcone synthase (CHS), a key enzyme in the phenylpropanoid pathway. Naringenin chalcone can spontaneously cyclize to naringenin (a flavanone). In plant cells, this process is catalyzed by chalcone isomerase.

Naringenin chalcone
Naringenin chalcone.svg
Names
Preferred IUPAC name
2′,4,4′,6′-Tetrahydroxychalcone
Other names
Chalconaringenin; Isosalipurpol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • 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/b6-3+
    Key: YQHMWTPYORBCMF-ZZXKWVIFSA-N
  • C1=CC(=CC=C1/C=C/C(=O)C2=C(C=C(C=C2O)O)O)O
Properties
C15H12O5
Molar mass 272.256 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).