trans-Chlorogenic acid → Gallic Acid

HRID 1923421Notes

Reaction equation

HRID 1923421 reaction equation
C1C(/C=C/C([O:11][C@H:12]2[C@H:17]([OH:18])[C@H:16]([OH:19])[CH2:15][C@@:14](O)([C:20]([OH:22])=[O:21])[CH2:13]2)=O)=CC(O)=C(O)C=1.[K]>O>[C:20]([OH:22])(=[O:21])[C:14]1[CH:15]=[C:16]([OH:19])[C:17]([OH:18])=[C:12]([OH:11])[CH:13]=1

Participants

4

Reactant 2

HCID 1794427trans-Chlorogenic acidHCID 5462222Potassium2×

Product 1

HCID 370Gallic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 20 g of commercially available instant coffee (Nescafe Gold Blend Red Label) was dissolved in 1400 mL of distilled water (which solution will hereinafter be called “Coffee P”), 30 g of activated carbon “Shirasagi WH2c 28/42” (product of Japan EnviroChemicals, Ltd., having an average pore size of 4.2 angstrom) was added to the resulting solution. The resulting mixture was stirred for one hour and then, filtered through a membrane filter (0.45 μm) to yield a filtrate (which will hereinafter be called “Coffee Q”). The resulting filtrate was freeze dried, whereby 15.8 g of brown powder was obtained. The resulting brown powder was dissolved in distilled water and amounts of chlorogenic acids and HHQ were determined by HPLC analysis as in Example 1. As a result, the chlorogenic acid content was 4.12 wt. %, while the HHQ content was below the detection limit (in accordance with the analysis conditions B). In addition, the potassium content was measured by ICP emission spectrometry. The potassium content in each of the raw material instant coffee and coffee treated with activated carbon was about. 4.2 wt. %. Analysis results of coffee P, coffee Q and gallic acid by HPLC are shown by the respective charts in FIGS. 1 and 2. In coffee Q, a peak in the vicinity of a retention time of 6.8 minutes disappears and it does not have a peak substantially. In FIG. 1, a represents the chart of coffee P, b represents the chart of coffee Q and c represents a chart of gallic acid. In FIG. 2, b represents the chart of coffee P, c represents the chart of coffee Q and a represents the chart of gallic acid.

Sources & evidence

ORD record
ord-9eed8e712fc9490ea02feb8363307ab1
Source dataset
uspto-grants-2012_05
Patent number
US08178148B2

Reaction notes

Loading…