Hydrogen Peroxide → (3,4,5-Trihydroxy-6-oxo-6h-benzo[7]annulene-1,8-diyl)bis[(2r,3r)-5,7-dihydroxy-3,4-dihydro-2h-chromene-2,3-diyl] bis(3,4,5-trihydroxybenzoate)

HRID 8516

Reaction equation

HRID 8516 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([OH:12])=[CH:8][C:9]=2[OH:11])[O:4][C@H:3]([C:13]2[CH:18]=[C:17](O)[C:16]([OH:20])=[C:15]([OH:21])[CH:14]=2)[C@@H:2]1[O:22][C:23]([C:25]1[CH:30]=[C:29]([OH:31])[C:28]([OH:32])=[C:27]([OH:33])[CH:26]=1)=[O:24].OO>CC(C)=O>[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([OH:12])=[CH:8][C:9]=2[OH:11])[O:4][C@H:3]([C:13]2[CH:18]=[C:18]3[C:13]([C@H:3]4[O:4][C:5]5[C:10](=[C:9]([OH:11])[CH:8]=[C:7]([OH:12])[CH:6]=5)[CH2:1][C@H:2]4[O:22][C:23]([C:25]4[CH:30]=[C:29]([OH:31])[C:28]([OH:32])=[C:27]([OH:33])[CH:26]=4)=[O:24])=[CH:14][C:15]([OH:21])=[C:16]([OH:20])[C:17]3=[C:16]([OH:20])[C:15](=[O:21])[CH:14]=2)[C@@H:2]1[O:22][C:23]([C:25]1[CH:26]=[C:27]([OH:33])[C:28]([OH:32])=[C:29]([OH:31])[CH:30]=1)=[O:24]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 65064Epigallocatechin Gallate

Product 1

HCID 467320(3,4,5-Trihydroxy-6-oxo-6h-benzo[7]annulene-1,8-diyl)bis[(2r,3r)-5,7-dihydroxy-3,4-dihydro-2h-chromene-2,3-diyl] bis(3,4,5-trihydroxybenzoate)Yield 10.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

ECG (1 g) and EGCG (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 4 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%). 100 mg theaflavin 3,3′-digallate was 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-85fb8685fe69496fa138220055177233
Source dataset
uspto-grants-2006_08
Patent number
US07087790B2

Linked notes

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