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Naringenin chalcone

Summary

Naringenin chalcone[1] 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
Names
Preferred IUPAC name
2′,4,4′,6′-Tetrahydroxychalcone
Other names
Chalconaringenin; Isosalipurpol
Identifiers
  • 25515-46-2 checkY
  • 73692-50-9 (non-specific) checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15413
ChemSpider
  • 4444447
KEGG
  • C06561
  • 5280960
UNII
  • YCF6Z24AS2 checkY
  • 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).
Infobox references

About Naringenin chalcone edit

Naringenin chalcone is an intermediate in flavonol biosynthesis, spontaneously metabolizing into naringenin (NAR) through the action of chalcone isomerase. Naringenin chalcone exhibits anti-inflammatory and antiallergic activities.

References edit

  1. ^ PubChem. "Naringenin chalcone". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-08-27.