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
ChemSpider	1405788 Y
ChEBI	CHEBI:16112 N
ChEMBL	CHEMBL284616 N
RTECS number	GU8480000
Jmol-3D images	Image 1
SMILES O=C(O)[C@]2(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)C2
InChI InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1 Y Key: CWVRJTMFETXNAD-JUHZACGLSA-N Y InChI=1/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1 Key: CWVRJTMFETXNAD-JUHZACGLBD
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
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chlorogenic acid is a hydroxycinnamic acid, a member of a family of naturally occurring organic compounds. These are esters of polyphenolic caffeic acid and cyclitol (-)-quinic acid.^[1] It is an important biosynthetic intermediate.^[2] It also is one of the phenols found in coffee, 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-CQA) and 5 (5-CQA). Isomerisation at position 1 has not yet been reported.^[1]

Biological importance

Chlorogenic 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 shown in in vitro studies to inhibit the hydrolysis of the enzyme glucose-6-phosphatase in an irreversible fashion.^{[citation needed]} This mechanism allows chlorogenic acid to reduce hepatic glycogenolysis (transformation of glycogen into glucose) and to reduce the absorption of new glucose.^{[citation needed]} 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.^{[citation needed]}

Isomers

Isomers of chlorogenic acid exist and are found in potatoes. They are 4-O-caffeoylquinic acid (crypto-chlorogenic acid), 5-O-caffeoylquinic acid (neo-chlorogenic acid), 3,4-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid^[12].

References

External links

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