Gallic Acid → 7Carboxy-2,3,4,6-tetrahydroxy-5h-benzocyclohepten-5one

HRID 8518

Reaction equation

HRID 8518 reaction equation
[CH:1]1[C:6]([C@@H:7]2[O:16]C3C=C(O)C=[C:11](O)[C:10]=3[CH2:9][C@@H:8]2[OH:19])=[CH:5][C:4]([OH:20])=[C:3]([OH:21])[CH:2]=1.[C:22]([OH:33])(=[O:32])C1C=C(O)C(O)=C(O)C=1.[OH:34]O>CC(C)=O>[CH:11]1[C:1]2[C:6](=[C:5]([OH:34])[C:4]([OH:20])=[C:3]([OH:21])[CH:2]=2)[C:7](=[O:16])[C:8]([OH:19])=[C:9]([C:22]([OH:33])=[O:32])[CH:10]=1

Participants

5

Reactant 3

HCID 370Gallic AcidHCID 784Hydrogen PeroxideHCID 182232(+)-Epicatechin

Product 1

HCID 861142727Carboxy-2,3,4,6-tetrahydroxy-5h-benzocyclohepten-5one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Epicatechin (EC) (0.5 g) and gallic acid (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1: 10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 2.0 mL of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 mL×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 70 mg epitheaflavic acid and 25 mg purpurogallin carboxylic acid were obtained.

Workup

  1. extractionThe reaction mixture was extracted by ethyl acetate (50 mL×3)
  2. concentrationAfter concentration
  3. washeluted with acetone-water solvent system (45%)

Sources & evidence

ORD record
ord-113213f2c3bc44289c47214ea6d78761
Source dataset
uspto-grants-2006_08
Patent number
US07087790B2

Linked notes

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