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 acid (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 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]

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^[13].

References

1. ^ ^{a b} Clifford, M. N.; Johnston, K. L.; Knigh, S.; Kuhnert, N. (2003). "Hierarchical Scheme for LC-MSⁿ Identification of Chlorogenic Acids". Journal of Agriculture and Food chemistry 51 (10): 2900–2911. doi:10.1021/jf026187q. PMID 12720369. 
2. ^ Wout Boerjan, John Ralph, Marie Baucher Annual Reviews Plant Biology 2003, volume 54, 519–46. doi:10.1146/annurev.arplant.54.031902.134938.
3. ^ Kweon,Mee-Hyang.; Hwang, Han-Joon. and Sung, Ha-Chin. (2001). "Identification and Antioxidant Activity of Novel Chlorogenic Acid Derivatives from Bamboo (Phyllostachys edulis).". Journal of Agriculture and Food Chemistry 49 (20): 4646–46552. doi:10.1021/jf010514x. http://pubs.acs.org/doi/abs/10.1021/jf010514x. 
4. ^ Clifford, M. N. (2003). "14. The analysis and characterization of chlorogenic acids and other cinnamates". In C. Santos-Buelga & G. Williamson (Eds.). Methods in Polyphenol Analysis. Cambridge: Royal Society of Chemistry. pp. 314–337. ISBN 0-85404-580-5. 
5. ^ Johnston, K. L.; Clifford, M.N.; Morgan, L.M. (October 1, 2003). "Coffee acutely modifies gastrointestinal hormone secretion and glucose tolerance in humans: glycemic effects of chlorogenic acid and caffeine.". American Journal of Clinical Nutrition (American Journal of Clinical Nutrition) 79 (4): 728–733. PMID 14522730. http://www.ajcn.org/cgi/content/full/78/4/728. 
6. ^ Clifford, M. N. (1999). "Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden.". Journal of the Science of Food and Agriculture 79 (3): 362–372. doi:10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D. 
7. ^ Paynter, Nina. P.; Yeh, H.C.; Voutilainen, S.; Schmidt, M.I.; Heiss, G.; Folsom, A.R.; Brancati, F.L.; Kao, W. H. L. (2006). "Coffee and Sweetened Beverage Consumption and the Risk of Type 2 Diabetes Mellitus" (abstract). American Journal of Epidemiology (Oxford Journals) 164 (11): 1075–1084. doi:10.1093/aje/kwj323. PMID 16982672. http://aje.oxfordjournals.org/cgi/content/abstract/164/11/1075. 
8. ^ Lincoln W. Morton; Rima Abu-Amsha Caccettah; Ian B. Puddey and Kevin D. Croft (2000). "Chemistry And Biological Effects Of Dietary Phenolic Compounds: Relevance To Cardiovascular Disease". Clinical and Experimental Pharmacology and Physiology 27 (3): 152–159. doi:10.1046/j.1440-1681.2000.03214.x. 
9. ^ Jassim, S.A.A; Naji, M.A. (2003). "Novel antiviral agents: a medicinal plant perspective". Journal of Applied Microbiology 95 (3): 412–427. doi:10.1046/j.1365-2672.2003.02026.x. PMID 12911688. 
10. ^ de Sotillo, D.R.; Hadley, M.; Wolf-Hall, C. (1998). "Potato Peel Extract a Nonmutagenic Antioxidant with Potential Antimicrobial Activity". Journal of Food Science 63 (5): 907. doi:10.1111/j.1365-2621.1998.tb17924.x. 
11. ^ Bowels, Bobby L.; Miller, A.J. (1994). "Caffeic Acid Activity Against Clostridium botulinum Spores". Journal of Food Science (Blackwell Publishing) 59 (4): 905. doi:10.1111/j.1365-2621.1994.tb08154.x. 
12. ^ Harding, Anna. "Coffee can be good for you, experts say". Archived from the original on 2007-05-22. http://web.archive.org/web/20070522155631/http://news.yahoo.com/s/nm/20070501/hl_nm/coffee_good_dc. Retrieved 2007-05-26. 
13. ^ Chemistry, Biochemistry, and Dietary Role of Potato Polyphenols. A Review. Mendel Friedman, J. Agric. Food Chem., 1997, 45 (5), pp 1523–1540, doi:10.1021/jf960900s

External links

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