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Chlorogenic acid

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Chlorogenic acid



IUPAC name[hide]


(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid


Other names[hide]


3-(3,4-Dihydroxycinnamoyl)quinate
3-(3,4-Dihydroxycinnamoyl)quinic acid
3-Caffeoylquinate
3-Caffeoylquinic acid
3-CQA
3-O-Caffeoylquinic acid
Chlorogenate
Chlorogenic acid
Heriguard
3-trans-Caffeoylquinic acid
Identifiers
CAS number 327-97-9
PubChem 1794427
ChemSpider 1405788
ChEBI CHEBI:16112
ChEMBL CHEMBL284616
RTECS number GU8480000
Jmol-3D images Image 1



SMILES [show]



InChI [show]
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


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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references


The term chlorogenic acids refers to a family of esters of hydroxycinnamic acids (caffeic acid, ferulic acid and p-coumaric acid) with quinic acid.[1]

The term chlorogenic acid (CGA) can also be used specifically for an ester of caffeic acid and (-)-quinic acid. 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]

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.


Contents
1 Chemical properties
2 Occurrences
3 Food additive
4 Biological effects
5 References

Chemical properties

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), 3,4-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid.[5] The epimer at position 1 has not yet been reported.[1] Isomers of chlorogenic acid are found in potatoes.
Occurrences

Chlorogenic acid can be found in bamboo Phyllostachys edulis.[6] as well as in many other plants.[7] It is one of the major phenolic compounds identified in peach[8] and in prunes.[9] It also is one of the phenols found in coffee. Chlorogenic acid, its 3-O-glucoside, 3-O-galactoside and 3-O-arabinoside can be found in the shoots of Calluna vulgaris (heather).[10]
Food additive

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.
Biological effects

Chlorogenic acid is reported to be a chemical sensitizer responsible for human respiratory allergy to certain types of plant materials.[11]

It could be involved in the laxative effect observed in prunes.[9]
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.
^ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Ligninbiosynthesis". Annual Review of Plant Biology 54: 519–46. doi:10.1146/annurev.arplant.54.031902.134938. PMID 14503002.
^ 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.
^ 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="-jsfa256">3.0.CO;2-D.
^ 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. 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.
^ 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)
^ 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?". Critical reviews in food science and nutrition 41 (4): 251–86. doi:10.1080/20014091091814. PMID 11401245.
^ Jalal, Mahbubul A.F.; Read, David J.; Haslam, E. (1982). "Phenolic composition and its seasonal variation in Calluna vulgaris". Phytochemistry 21 (6): 1397. doi:10.1016/0031-9422(82)80150-7.
^ Freedman, Samuel O.; Shulman, Robert; Krupey, John; Sehon, A.H. (1964). "Antigenic properties of chlorogenic acid". Journal of Allergy 35 (2): 97. doi:10.1016/0021-8707(64)90023-1.

[hide]

v
t
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Types of hydroxycinnamic acids


Hydroxycinnamic acids
Caffeic acid | Cinnamic acid | Coumaric acids (p-Coumaric acid, o-Coumaric acid, m-Coumaric acid) | Diferulic acid | Ferulic acid | Plicatins A and B | Sinapinic acid


Glycosides
Glycosides of caffeic acid : Chlorogenic acid (3-Caffeoylquinic acid) | Dactylifric acid (3-O-caffeoylshikimic acid) | Neochlorogenic acid (5-O-Caffeoylquinic acid) | Cynarine (1,5-dicaffeoylquinic acid)
Other glycosides: Ferulic acid glucoside | p-Coumaric acid glucoside


Esters
Tartaric acid esters : Caftaric acid, Cichoric acid, Coutaric acid, Fertaric acid | Ethyl esters : Ethyl caffeate | Methyl esters : Methyl caffeate | Phenethyl ester : Caffeic acid phenethyl ester | Esters of coenzyme A : Cinnamoyl-Coenzyme A, Coumaroyl-Coenzyme A | Ester of glutathione : Grape reaction product

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