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Chemical name 3-*oxy]-1,4,5-
trihydroxycyclohexanecarboxylic acid
Chemical formula C16H18O9
Molecular mass 354.31 g/mol
CAS number *
Density 1.28 g/cm3
Melting point 207 - 209 °C
Boiling point unknown °C
SMILES O*2*(O)C*
(O)(C*2OC(=O)\C=C/
c1ccc(O)c(O)c1)C(O)=O
Chemical infobox

Chlorogenic acid is 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.

Chemical properties


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

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 g/µL, 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.

Pharmaceutical & industrial applications


This substance can be used as anti-infectious active ingredient, it has wide anti-virus, anti-bacteria effects, and has relatively lower toxicity and side-effects. It has obvious anti-infectious effects, and does not like to lead Anti-microbial resistance. Due to its obvious anti-infectious effects, it not only can be used in pharmaceutical field but can be used widely in many other fields like food, feed additives, cosmetics also.

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 glucagen, 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.

References


Carboxylate esters | Carboxylic acids

Chlorogensäure

 

This article is licensed under the GNU Free Documentation License. It uses material from the "Chlorogenic acid".

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