Chlorogenic acid


Chlorogenic acid
Chlorogenic acid
Identifiers
CAS number 327-97-9 YesY
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
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
NFPA 704.svg
0
1
0
 N acid (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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] It also is one of the phenols found in coffee, 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

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-CQA) and 5 (5-CQA). Isomerisation at position 1 has not yet been reported.[1]

Biological importance

Chlorogenic acid is an important intermediate in lignin biosynthesis.

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.

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]

Isomers

Isomers of chlorogenic acid exist and 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[13].

References

  1. ^ 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. 
  2. ^ Wout Boerjan, John Ralph, Marie Baucher Annual Reviews Plant Biology 2003, volume 54, 519–46. doi:10.1146/annurev.arplant.54.031902.134938.
  3. ^ 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. 
  4. ^ 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. 
  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. 
  6. ^ 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. 
  7. ^ 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:10.1093/aje/kwj323. PMID 16982672. http://aje.oxfordjournals.org/cgi/content/abstract/164/11/1075. 
  8. ^ 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:10.1046/j.1440-1681.2000.03214.x. 
  9. ^ Jassim, S.A.A; Naji, M.A. (2003). "Novel antiviral agents: a medicinal plant perspective". Journal of Applied Microbiology 95 (3): 412–427. doi:10.1046/j.1365-2672.2003.02026.x. PMID 12911688. 
  10. ^ 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:10.1111/j.1365-2621.1998.tb17924.x. 
  11. ^ Bowels, Bobby L.; Miller, A.J. (1994). "Caffeic Acid Activity Against Clostridium botulinum Spores". Journal of Food Science (Blackwell Publishing) 59 (4): 905. doi:10.1111/j.1365-2621.1994.tb08154.x. 
  12. ^ Harding, Anna. "Coffee can be good for you, experts say". Archived from the original on 2007-05-22. http://web.archive.org/web/20070522155631/http://news.yahoo.com/s/nm/20070501/hl_nm/coffee_good_dc. Retrieved 2007-05-26. 
  13. ^ 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

External links


Wikimedia Foundation. 2010.

Look at other dictionaries:

  • chlorogenic acid — | ̷ ̷ ̷ ̷|jenik noun Etymology: International Scientific Vocabulary chlor + genic; originally formed as French chlorogénique : a crystalline acid C15H17O7COOH occurring in coffee beans as the potassium caffeine salt, in potatoes, and in other… …   Useful english dictionary

  • chlorogenic acid — chlo·ro·gen·ic acid .klōr ə .jen ik , .klȯr n a crystalline acid C16H18O9 occurring in various plant parts (as potatoes or coffee beans) * * * chlo·ro·gen·ic ac·id (kloґro jen″ik) a phenol compound important in plant metabolism, found in… …   Medical dictionary

  • chlorogenic acid — noun Date: circa 1889 a crystalline acid C16H18O9 occurring in various plant parts (as coffee beans) …   New Collegiate Dictionary

  • chlorogenic acid — /klawr euh jen ik, klohr , klawr , klohr /, Biochem. a colorless crystalline acid, C16H18O9, that is important in plant metabolism and is purportedly responsible for the browning or blackening of cut apples, potatoes, and other fruits and… …   Universalium

  • chlorogenic acid — noun Any of a family of phenolic carboxylic acids, found in coffee, that have antioxidant properties …   Wiktionary

  • Caffeic acid — Chembox new Name = Caffeic acid ImageFile = Caffeic acid.svg ImageName = Caffeic acid ImageFile1 = CaffeicAcid3d.png ImageName1 = Caffeic acid IUPACName = 3 (3,4 Dihydroxyphenyl 3,4 Dihydroxy cinnamic acid trans Caffeate 3,4 Dihydroxy trans… …   Wikipedia

  • Hydroxycinnamic acid — Hydroxycinnamic acids are a class of polyphenols having a C6 C3 skeleton. These compounds are hydroxy derivatives of cinnamic acid. In the category of phytochemicals that can be found in food, there are : Alpha cyano 4 hydroxycinnamic acid… …   Wikipedia

  • Cichoric acid — IUPAC name (2R,3R) 2,3 bis{[(E) 3 (3,4 dihydroxyphenyl)prop 2 enoyl]oxy}butanedioic acid …   Wikipedia

  • Ferulic acid — IUPAC name (E) 3 (4 hydroxy 3 methoxy phenyl)prop 2 enoic acid …   Wikipedia

  • Coumaric acid — p Coumaric acid …   Wikipedia