Chlorogenic acid
From Wikipedia, the free encyclopedia
| Chlorogenic acid | |
|---|---|
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| IUPAC name |
(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid
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| 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  |
| 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
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| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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]
Contents |
[edit] 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]
[edit] Biological importance
This acid is an important intermediate in lignin biosynthesis.
[edit] 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.
[edit] 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]
[edit] References
- ^ 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: 2900–2911. doi:.
- ^ Wout Boerjan, John Ralph, Marie Baucher Annual Reviews Plant Biology 2003, volume 54, 519–46. doi:10.1146/annurev.arplant.54.031902.134938.
- ^ Identification and Antioxidant Activity of Novel Chlorogenic Acid Derivatives from Bamboo (Phyllostachys edulis). Mee-Hyang Kweon, Han-Joon Hwang, and Ha-Chin Sung, J. Agric. Food Chem., 2001, 49 (10), pp 4646–4655
- ^ 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.
- ^ 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.
- ^ Clifford, M. N. (1999). "Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden.". Journal of the Science of Food and Agriculture 79: 362–372. doi:.
- ^ 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:. PMID 16982672. http://aje.oxfordjournals.org/cgi/content/abstract/164/11/1075.
- ^ 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:.
- ^ Jassim, S.A.A.; Naji, M.A. (2003). "Novel antiviral agents: a medicinal plant perspective". Journal of Applied Microbiology 95 (3): 412–427. doi:.
- ^ 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:.
- ^ Bowels, Bobby L.; Miller, A.J. (1994). "Caffeic Acid Activity Against Clostridium botulinum Spores". Journal of Food Science (Blackwell Publishing) 59 (4): 905. doi:.
- ^ Harding, Anna. "Coffee can be good for you, experts say". http://news.yahoo.com/s/nm/20070501/hl_nm/coffee_good_dc. Retrieved 2007-05-26.
