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  |
| PubChem | 1794427 |
| 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−1 |
| Density | 1.28 g/cm3 |
| Melting point |
207-209 °C, 480-482 K, 405-408 °F |
| 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 (CGA) is a natural chemical compound which is the ester of caffeic acid and (-)-quinic acid. It is an important biosynthetic intermediate.[1] Chlorogenic acid is an important intermediate in lignin biosynthesis. This compound, long known as an antioxidant, may also slow the release of glucose into the bloodstream after a meal.[2]
The term chlorogenic acids can also refer more broadly to a related family of esters of hydroxycinnamic acids (caffeic acid, ferulic acid and p-coumaric acid) with quinic acid.[3]
Chlorogenic acids contain no chlorine. The name comes from the Greek χλωρός (light green) and -γένος (a suffix meaning "giving rise to"), because of the green color produced when chlorogenic acids are oxidized.
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Chemical properties [edit]
Structurally, chlorogenic acid is the ester formed between caffeic acid and L-quinic acid.[4]
Isomers of chlorogenic acid include 4-O-caffeoylquinic acid (cryptochlorogenic acid or 4-CQA), 5-O-caffeoylquinic acid (neochlorogenic acid or 5-CQA). The epimer at position 1 has not yet been reported.[3]
Isomer containing two caffeic acid molecules are called isochlorogenic acid. There are several isomers such as 3,4-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid.[5]
Chlorogenic acid is freely soluble in ethanol and acetone.
Natural occurrences [edit]
Isomers of chlorogenic acid are found in potatoes.[6]
Chlorogenic acid can be found in bamboo Phyllostachys edulis.[7] as well as in many other plants.[8] It is one of the major phenolic compounds identified in peach[9] and in prunes.[10] It also is one of the phenols found in green coffee bean extract.[11]
Chlorogenic acid, its 3-O-glucoside, 3-O-galactoside and 3-O-arabinoside can be found in the shoots of Calluna vulgaris (heather).[12]
Food additive [edit]
Chlorogenic acid is marketed under the tradename Svetol in Norway and the United Kingdom as a food additive used in coffee, chewing gum, and mints. Dried sunflower leaves collected immediately after opening are processed into 98.38% chlorogenic acid extract and marketed in Bulgaria under the name of "Yamiagra" - "Yummyiagra".
Biological effects [edit]
A review article describes chlorogenic acid as having antihypertensive effects.[13]
Chlorogenic acid is reported to be a chemical sensitizer responsible for human respiratory allergy to certain types of plant materials.[14]
It could be involved in the laxative effect observed in prunes.[10]
References [edit]
- ^ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Lignin biosynthesis". Annu. Rev. Plant Biol. 54: 519–46. doi:10.1146/annurev.arplant.54.031902.134938. PMID 14503002.
- ^ Johnston, K. L.; Clifford, M. N.; Morgan, L. M. (October 2003). "Coffee acutely modifies gastrointestinal hormone secretion and glucose tolerance in humans: glycemic effects of chlorogenic acid and caffeine". Am. J. Clin. Nutrit. 78 (4): 728–733. PMID 14522730.
- ^ a b Clifford, M. N.; Johnston, K. L.; Knigh, S.; Kuhnert, N. (2003). "Hierarchical Scheme for LC-MSn Identification of Chlorogenic Acids". J. Agric. Food Chem. 51 (10): 2900–2911. doi:10.1021/jf026187q. PMID 12720369.
- ^ Clifford, M. N. (1999). "Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden". J. Sci. Food Agr. 79 (3): 362–372. doi:10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D.
- ^ Corse, J.; Lundin, R. E.; Waiss, A. C. (May 1965). "Identification of several components of isochlorogenic acid". Phytochem. 4 (3): 527–529. doi:10.1016/S0031-9422(00)86209-3.
- ^ Mendel Friedman (1997). "Chemistry, Biochemistry, and Dietary Role of Potato Polyphenols. A Review". J. Agric. Food Chem. 45 (5): pp 1523–1540. doi:10.1021/jf960900s.
- ^ Kweon, Mee-Hyang; Hwang, Han-Joon; Sung, Ha-Chin (2001). "Identification and Antioxidant Activity of Novel Chlorogenic Acid Derivatives from Bamboo (Phyllostachys edulis)". J. Agric. Food Chem. 49 (20): 4646–46552. doi: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.
- ^ Cheng, G. W.; Crisosto, C. H. (September 1995). "Browning Potential, Phenolic Composition, and Polyphenoloxidase Activity of Buffer Extracts of Peach and Nectarine Skin Tissue". J. Amer. Soc. Hort. Sci. 120 (5): 835–838.
- ^ a b Stacewicz-Sapuntzakis, M; Bowen, PE; Hussain, EA; Damayanti-Wood, BI; Farnsworth, NR (2001). "Chemical composition and potential health effects of prunes: a functional food?". Crit. Rev. Food Sci. Nutr. 41 (4): 251–86. doi:10.1080/20014091091814. PMID 11401245.
- ^ Igho Onakpoya, Rohini Terry, and Edzard Ernst (2010). "The Use of Green Coffee Extract as a Weight Loss Supplement: A Systematic Review and Meta-Analysis of Randomised Clinical Trials". Complementary Medicine: 1.
- ^ Jalal, Mahbubul A.F.; Read, David J.; Haslam, E. (1982). "Phenolic composition and its seasonal variation in Calluna vulgaris". Phytochem. 21 (6): 1397–1401. doi:10.1016/0031-9422(82)80150-7.
- ^ Zhao, Y.; Wang, J.; Ballevre, O.; Luo, H.; Zhang, W. (2011). "Antihypertensive effects and mechanisms of chlorogenic acids.". Hypertens Res. 35 (4): 370–4. doi:10.1038/hr.2011.195.
- ^ Freedman, Samuel O.; Shulman, Robert; Krupey, John; Sehon, A.H. (1964). "Antigenic properties of chlorogenic acid". J. Allergy 35 (2): 97–107. doi:10.1016/0021-8707(64)90023-1.
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