Chlorogenic acid

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Chlorogenic acid

Chemical name	3-[[3-(3,4-Dihydroxyphenyl)- 1-oxo-2-propenyl]oxy]-1,4,5- trihydroxycyclohexanecarboxylic acid
Chemical formula	C₁₆H₁₈O₉
Molecular mass	354.31 g/mol
CAS number	[327-97-9]
Density	1.28 g/cm³
Melting point	207 - 209 °C
Boiling point	unknown °C
SMILES	O[C@@H]2[C@H](O)C[C@] (O)(C[C@H]2OC(=O)\C=C/ c1ccc(O)c(O)c1)C(O)=O
Disclaimer and references

Chlorogenic acid, an ester of caffeic acid and quinic acid, is a major phenolic compound in coffee, isolated from the leaves and fruits of dicotyledonous plants. This compound, long known as an antioxidant, also slows the release of glucose into the bloodstream after a meal.

1 Chemical properties
2 Biological importance
3 Pharmaceutical & industrial applications
4 Recent studies
5 References

[edit] Chemical properties

Structurally, chlorogenic acid is the ester of caffeic acid with the 3-hydroxyl group of quinic acid.

[edit] Biological importance

This acid is an important factor in plant metabolism. It is also an antioxidant and an inhibitor of the tumor promoting activity of phorbol esters; at concentrations as high as 100 µg/L, does not inhibit the 5-lipoxygenase activity of ionophore-stimulated human polymorphonuclear leukocytes.

Chlorogenic acid and caffeic acid are antioxidants in vitro and might therefore contribute to the prevention of cardiovascular disease.

[edit] Pharmaceutical & industrial applications

This substance is claimed to have antiviral and antibacterial effects with relatively low toxicity and side effects, alongside properties that do not lead antimicrobial resistance. Potential uses are suggested in pharmaceuticals, foodstuffs, feed additives, and cosmetics.^{[citation needed]}

Chlorogenic acid is marketed under the tradename Svetol® in Norway and the United Kingdom as a food additive used in coffee, chewing gum, and mints to promote weight reduction. [1] [2]

[edit] Recent studies

Chlorogenic acid has been proven in animal studies in vitro to inhibit the hydrolysis of the glucose-6-phosphate enzyme in an irreversible fashion. This mechanism allows chlorogenic acid to reduce hepatic glycogenolysis (transformation of glycogen into glucose) and to reduce the absorption of new glucose. In addition, in vivo studies on animal subjects have demonstrated that the administration of chlorogenic acid lessens the hyperglycemic peak resulting from the glycogenolysis brought about by the administering of glucagon, a hyperglycemiant hormone. The studies also confirmed a reduction in blood glucose levels and an increase in the intrahepatic concentrations of glucose-6-phosphate and of glycogen.