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Dihydrogossypetin

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Dihydrogossypetin
Names
IUPAC name (2R,3R)-3,3′,4′,5,7,8-Hexahydroxyflavan-4-one
Systematic IUPAC name (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxy-2,3-dihydro-4H-1-benzopyran-4-one
Other names 2,3-Dihydrogossypetin
3′,4′,5,7,8-pentahydroxyflavanonol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H12O8/c16-6-2-1-5(3-7(6)17)14-13(22)12(21)10-8(18)4-9(19)11(20)15(10)23-14/h1-4,13-14,16-20,22H/t13-,14+/m0/s1Key: ZHPLPRUARZZBET-UONOGXRCSA-N
  • InChI=1/C15H12O8/c16-6-2-1-5(3-7(6)17)14-13(22)12(21)10-8(18)4-9(19)11(20)15(10)23-14/h1-4,13-14,16-20,22H/t13-,14+/m0/s1Key: ZHPLPRUARZZBET-UONOGXRCBO
SMILES
  • C1=CC(=C(C=C1C2C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O)OC1=CC(=C(C=C12C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O)O
Properties
Chemical formula C15H12O8
Molar mass 320.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Dihydrogossypetin is a flavanonol, a type of flavonoid.

Biosynthesis

The enzyme Taxifolin 8-monooxygenase hydroxylates taxifolin using NADH, NADPH, H, and O2 to produce 2,3-dihydrogossypetin, NAD, NADP, and H2O.


References

  1. Jeffrey, A. M.; Jerina, D. M.; Self, R.; Evans, W. C. (1972). "The bacterial degradation of flavonoids. Oxidative fission of the A-ring of dihydrogossypetin by a Pseudomonas sp". The Biochemical Journal. 130 (2): 383–90. doi:10.1042/bj1300383. PMC 1174417. PMID 4198081.
Flavanonols and their glycosides
3-Hydroxyflavanones:
O-methylated flavanonols
dihydroflavonol 3-O-glycosides
Glycosides
Acetylated glycosides


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