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 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. IUPAC nomenclature is a systematic way of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change state from a liquid to a gas throughout the bulk of the liquid. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII alpha-numeric strings. ... In organic chemistry and biochemistry esters are substances where an organic group replaces a hydrogen atom (or more than one) in an oxygen acid. ... Caffeic acid, C9H8O4 is a carboxylic acid found in many fruits, vegetables, seasonings and beverages, principally in conjugated forms such as chlorogenic acid. ... Phenol, also known under the old name carbolic acid, is a colorless crystalline solid with a typical sweet tarry odor. ... Coffee beans and a cup of coffee Coffee as a drink, usually served hot, is prepared from the roasted seeds (beans) of the coffee plant. ... Orders see text Dicotyledons or dicots are flowering plants whose seed contains two embryonic leaves or cotyledons. ... An antioxidant is a chemical that prevents the oxidation of other chemicals. ... A space-filling model of glucose Glucose, a simple monosaccharide sugar, is one of the most important carbohydrates and is used as a source of energy in animals and plants. ... Red blood cells (erythrocytes) are present in the blood and help carry oxygen to the rest of the cells in the body Blood is a circulating tissue composed of fluid plasma and cells (red blood cells, white blood cells, platelets). ...

Chemical properties

Structurally, chlorogenic acid is the ester of caffeic acid with the 3-hydroxyl group of quinic acid. In organic chemistry and biochemistry esters are substances where an organic group replaces a hydrogen atom (or more than one) in an oxygen 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. An antioxidant is a chemical that prevents the oxidation of other chemicals. ...

Chlorogenic acid and caffeic acid are antioxidants in vitro and might therefore contribute to the prevention of cardiovascular disease. An antioxidant is a chemical that prevents the oxidation of other chemicals. ... Wiktionary has a definition of: In vitro In vitro (Latin: within glass) means within a test tube, or, more generally, outside a living organism or cell. ...

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. Wiktionary has a definition of: In vitro In vitro (Latin: within glass) means within a test tube, or, more generally, outside a living organism or cell. ... Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. ... Glycogenolysis is the catabolism of glycogen (requiring removal of glucose unit from glycogen and addition of phosphate) thus producing glucose 1-phosphate, and subsequently reconfigured (C-1 -> C-6) to yield glucose 6-phosphate, a potent reaction intermediary leading to glucose available to the blood and brain, pyruvic acid (yet... A space-filling model of glucose Glucose, a simple monosaccharide sugar, is one of the most important carbohydrates and is used as a source of energy in animals and plants. ... In vivo (Latin for (with)in the living). ... Hyperglycemia or High Blood Sugar is a condition in which an excessive amount of glucose circulates in the blood plasma. ... Glycogen is the principal storage form of glucose in animal cells. ...

References

• "Molecule of the Week - chlorogenic acid". Chlorogenic acid. URL accessed on September 5, 2005.
• "China Great Vista Chemicals". Chlorogenic acid. URL accessed on September 5, 2005.