Chlorogenic acid
| Chlorogenic acid | |
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(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 |
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| Identifiers | |
| CAS number | 327-97-9  |
| ChemSpider | 1405788 |
| ChEBI | CHEBI:16112  |
| ChEMBL | CHEMBL284616 |
| RTECS number | GU8480000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C16H18O9 |
| Molar mass | 354.31 g/mol |
| Exact mass | 354.095082 u |
| 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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 (verify) (what is:  / ?)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 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] Chlorogenic acid is an important intermediate in lignin biosynthesis. This compound, long known as an antioxidant, also slows the release of glucose into the bloodstream after a meal.[3]
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[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).[4]
Isomerisation 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] Isomers of chlorogenic acid 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.[5]
[edit] Occurrences
Chlorogenic acid can be found in many plants, such as bamboo Phyllostachys edulis[6], as well as many other plants.[7] It is one of the major phenolic compounds identified in peach.[8] It could be involved in the laxative effect observed in prunes.[9] It also is one of the phenols found in coffee. 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.
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]
[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 (10): 2900–2911. doi:10.1021/jf026187q. PMID 12720369.
- ^ Wout Boerjan, John Ralph, Marie Baucher Annual Reviews Plant Biology 2003, volume 54, 519–46. doi:10.1146/annurev.arplant.54.031902.134938.
- ^ 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 (3): 362–372. doi:10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D.
- ^ 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
- ^ 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.
- ^ 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.
- ^ Browning Potential, Phenolic Composition, and Polyphenoloxidase Activity of Buffer Extracts of Peach and Nectarine Skin Tissue. Guiwen W. Cheng and Carlos H. Crisosto, J. Amer. Soc. Hort. Sci., 1995, 120(5), pages 835-838, (article)
- ^ Stacewicz-Sapuntzakis, M; Bowen, PE; Hussain, EA; Damayanti-Wood, BI; Farnsworth, NR (2001). "Chemical composition and potential health effects of prunes: a functional food?". Critical reviews in food science and nutrition 41 (4): 251–86. doi:10.1080/20014091091814. PMID 11401245.
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