Chlorogenic acid

Chlorogenic acid
IUPAC name	(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid
Other names	3-(3,4-Dihydroxycinnamoyl)quinate 3-(3,4-Dihydroxycinnamoyl)quinic acid 3-Caffeoylquinate 3-Caffeoylquinic acid 3-O-Caffeoylquinic acid Chlorogenate Chlorogenic acid Heriguard Hlorogenate Hlorogenic acid 3-trans-Caffeoylquinic acid
Identifiers
CAS number	327-97-9 Y
RTECS number	GU8480000
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
Properties
Molecular formula	C16H18O9
Molar mass	354.31 g/mol
Exact mass	354.095082
Density	1.28 g/cm3
Melting point	207 - 209 °C
Hazards
MSDS	External MSDS
R-phrases	-
S-phrases	S24, S25, S28, S37, S45
NFPA 704	0 1 0
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chlorogenic acid is a family of naturally occurring organic compounds. These are esters of cinnamic acids and (-)-quinic acid.^[1] It is an important biosynthetic intermediate.^[2] It also is one of the phenols found in coffee, in the bamboo Phyllostachys edulis^[3] as well as many other plants.^[4] This compound, long known as an antioxidant, also slows the release of glucose into the bloodstream after a meal.^[5]

Chemical properties

Structurally, chlorogenic acid (CGA) is the ester formed between caffeic acid and (L)-quinic acid (1L-1(OH),3,4/5-tetrahydroxycyclohexanecarboxylic acid).^[6] Isomerisation of chlorogenic acid have been reported with 3 isomerisations of the quinic acid in position 3, (3-CQA), 4 (4-CGA) and 5 (5-CQA). Isomerisation at position 1 has not yet been reported.^[1]

Biological importance

This acid is an important intermediate in lignin biosynthesis.

Potential as antioxidants

It is also an antioxidant and an inhibitor of the tumor promoting activity of phorbol esters. Chlorogenic acid and caffeic acid are antioxidants in vitro and might therefore contribute to the prevention of Type 2 Diabetes Mellitus^[7] and cardiovascular disease.^[8] It is claimed to have antiviral,^[9] antibacterial^[10] and antifungal^[11] effects with relatively low toxicity and side effects, alongside properties that do not lead to 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 active ingredient used in coffee, chewing gum, and mints to promote weight reduction.

Recent studies

Chlorogenic acid has been proven in animal studies in vitro to inhibit the hydrolysis of the enzyme glucose-6-phosphatase 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.^[12]

References

External links

• http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1794427&loc=ec_rcs