Chlorogenic acid

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Chlorogenic acid
Chlorogenic acid
Identifiers
CAS number 327-97-9 YesY
PubChem 1794427
ChemSpider 1405788 YesY
ChEBI CHEBI:16112 N
ChEMBL CHEMBL284616 N
RTECS number GU8480000
Jmol-3D images Image 1
Properties
Molecular formula C16H18O9
Molar mass 354.31 g mol−1
Density 1.28 g/cm3
Melting point 207 to 209 °C (405 to 408 °F; 480 to 482 K)
Hazards
MSDS External MSDS
R-phrases -
S-phrases S24 S25 S28 S37 S45
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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, 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 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.

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]

Isomers containing two caffeic acid molecules are called isochlorogenic acid. It can be found in coffee.[5] There are several isomers such as 3,4-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid[6] Cynarine (1,5-dicaffeoylquinic acid) is an other isomer with two caffeic acid molecules..

Chlorogenic acid UV vis spectrum with a maximum of absorbance at 325 nm

Chlorogenic acid is freely soluble in ethanol and acetone.

Natural occurrences[edit]

Isomers of chlorogenic acid are found in potatoes.[7]

Chlorogenic acid can be found in bamboo Phyllostachys edulis.[8] as well as in many other plants.[9] It is one of the major phenolic compounds identified in peach[10] and in prunes.[11] It also is one of the phenols found in green coffee bean extract.[12]

Chlorogenic acid, its 3-O-glucoside, 3-O-galactoside and 3-O-arabinoside can be found in the shoots of Calluna vulgaris (heather).[13]

Food additive[edit]

Chlorogenic acid is marketed under the tradename Svetol, a standardized green coffee extract, as a food additive used in coffee products, chewing gum, and mints, and also as a stand-alone product. Dried sunflower leaves collected immediately after opening are processed into 98.38% chlorogenic acid extract and marketed in Bulgaria under the name of "Yamiagra"or "Yummyiagra".

Biological effects[edit]

A review article describes chlorogenic acid as having antihypertensive effects.[14]

Chlorogenic acid is reported to be a chemical sensitizer responsible for human respiratory allergy to certain types of plant materials.[15]

It could be involved in the laxative effect observed in prunes.[11]

One study showed that chlorogenic acid may have weak psychostimulant effects in mice.[16]

Another study showed chlorogenic acid to have a protective effect in neuroinflammatory conditions on dopaminergic neurons.[17]

In an online news story article appearing in MSN Healthy Living, accessed in May 2014, scientists gave mice nitric oxide (NO), which creates oxidative stress and promotes the formation of certain harmful free radicals, leading to (among other problems) retinal degeneration, which impairs the crucial rods and cones and leads to other retinal tissue damage, and ultimately, loss of sight. Any animal's retina- whether in mice or in humans or other species- is very metabolically active, and requires, like the brain it communicates with via the optic nerve, a consistently high and steady supply of uncontaminated oxygen. The mice exposed to the nitric oxide who were pretreated with chlorogenic acid (CLA) did not develop any detectable signs of retinal damage. It is hoped that, after subsequent larger studies in animals and humans, a special brew of coffee could ultimately be developed that would be geared toward ensuring that the retina more directly receives the CLA, as opposed to normal coffees where that may or may not be the case (alternatively, CLA-containing eye drops could also be developed).[18]

References[edit]

  1. ^ 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. 
  2. ^ 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. 
  3. ^ a b Clifford, M. N.; Johnston, K. L.; Knigh, S.; Kuhnert, N. (2003). "Hierarchical Scheme for LC-MSn Identification of Chlorogenic Acids". Journal of Agricultural and Food Chemistry 51 (10): 2900–2911. doi:10.1021/jf026187q. PMID 12720369. 
  4. ^ 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. 
  5. ^ Isochlorogenic Acid. Isolation from Coffee and Structure Studies. H. M. Barnes, J. R. Feldman and W. V. White, J. Am. Chem. Soc., 1950, volume 72, issue 9, pages 4178–4182, doi:10.1021/ja01165a095
  6. ^ 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. 
  7. ^ Mendel Friedman (1997). "Chemistry, Biochemistry, and Dietary Role of Potato Polyphenols. A Review". Journal of Agricultural and Food Chemistry 45 (5): pp 1523–1540. doi:10.1021/jf960900s. 
  8. ^ Kweon, Mee-Hyang; Hwang, Han-Joon; Sung, Ha-Chin (2001). "Identification and Antioxidant Activity of Novel Chlorogenic Acid Derivatives from Bamboo (Phyllostachys edulis)". Journal of Agricultural and Food Chemistry 49 (20): 4646–46552. doi:10.1021/jf010514x. 
  9. ^ 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. 
  10. ^ 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. 
  11. ^ 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. 
  12. ^ 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. 
  13. ^ 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. 
  14. ^ 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. PMID 22072103. 
  15. ^ 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. 
  16. ^ "Effects of chlorogenic acid and its metabolites on spontaneous locomotor activity in mice.". Biosci Biotechnol Biochem 70 (10): 2560–3. 2006. doi:10.1271/bbb.60243. PMID 17031047. 
  17. ^ "Chlorogenic acid inhibits LPS-induced microglial activation and improves survival of dopaminergic neurons.". Brain Res Bull 88 (5): 487–94. 2012. doi:10.1016/j.brainresbull.2012.04.010. PMID 22580132. 
  18. ^ http://healthyliving.msn.com/diseases/vision/why-coffee-may-be-good-for-your-eyes