Chlorogenic acid

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Structural formula
Structural formula of chlorogenic acid
General
Surname Chlorogenic acid
other names

(1 S , 3 R , 4 R , 5 R ) -3 - [(E) -3- (3,4-dihydroxyphenyl) prop-2-enoyl] oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid ( IUPAC )

Molecular formula C 16 H 18 O 9
Brief description

colorless solid

External identifiers / databases
CAS number
  • 202650-88-2 ( E ) -chlorogenic acid
  • 327-97-9 (unspec.)
PubChem 1794427
ChemSpider 1405788
DrugBank DB12029
Wikidata Q421964
properties
Molar mass 354.31 g mol −1
Physical state

firmly

Melting point

about 208 ° C (decomposition)

pK s value

2.66 (27 ° C)

solubility
  • soluble in water
  • Easily soluble in alcohol and acetone
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

4 g kg −1 ( LD Lo ,  rat ,  ip )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlorogenic acid is a natural substance that occurs in numerous plants; From a chemical point of view, it is an ester of caffeic acid with quinic acid as the alcoholic component.

Lightly roasted coffee beans

Particularly well known is the as an ingredient of coffee , but it is also found in many plant species as chrozophora , cinchona trees ( Cinchona ), Marsh , Baldrianen ( Valeriana ), Greis herbs ( Senecio ) and locust herbs ( Hypericum ) and in the silver fir ( Abies alba ), in hawthorns ( Crataegus ), in the artichoke , in the red coneflower ( Echinacea ), in potatoes and in the nettle .

Among other things, chlorogenic acid is responsible for complaints in coffee drinkers with sensitive stomachs, which is why the chlorogenic acid content is reduced through special roasting processes. Slow roasting for around 20 minutes at temperatures around 200 ° C breaks down more chlorogenic acid than quick, three to five-minute roasting at temperatures of 400 to 600 ° C. 100 g of roasted coffee contain approx. 3.5 g of chlorogenic acid. However, arguments against chlorogenic acid as the main cause of stomach irritation are that animal experiments have shown that it has improved gastric ulcers and that other foods containing chlorogenic acid do not cause stomach problems.

Chlorogenic acid forms complexes as polyphenols . Their complexes with iron (III) ions are colored black. This can lead to corresponding discolouration of vegetables containing chlorogenic acid, for example when cooking potatoes in iron pots. The effect is desirable in the production of moss cake . Its topping turns green because the chlorogenic acid contained in the sprinkled coffee reacts with the protein of the topping. This green color in an alkaline solution is very likely the origin of the name of chlorogen ( ancient Greek χλωρός chlōrós "light green" and -gen ).

Biological effects

Chlorogenic acid has shown effects on biological systems in various studies. It should be noted that although these are effects that have been proven by scientific studies, they should not be understood as medicinal effects . This would require considerably more extensive investigations.

Chlorogenic acid is a well-known antioxidant and its isomers protect the DNA from damage, an effect that was even effective against damage from ionizing radiation in cell experiments . It slows down the absorption of sugar into the blood after a meal . This supports the observation that chlorogenic acid showed an antidiabetic effect in animal models . An antihypertensive effect has also been discovered in healthy people. Chlorogenic acid inhibits platelet aggregation ( blood clotting ). In animal experiments on Swiss mice (laboratory mouse strain), a positive effect was demonstrated on various gastric ulcer models . It has been shown that chlorogenic acid is able to inhibit liver inflammation . In the cell model, it was shown that chlorogenic acid can trigger apoptosis (programmed cell death) in cancer cells.

It has also been discovered that very high doses of chlorogenic acid (around 10 times what is found in normal dietary supplements) can increase the level of homocysteine in the blood. Homocysteine ​​is an important risk factor for cardiovascular diseases .

Individual evidence

  1. ↑ a b c Entry on Chlorogenic Acid Hydrate at TCI Europe, accessed on February 8, 2019.
  2. ↑ a b c data sheet Chlorogenic acid hemihydrate, 97% from AlfaAesar, accessed December 6, 2019 ( PDF )(JavaScript required) .
  3. ↑ a b Entry on chlorogenic acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ^ Toxicology and Applied Pharmacology . , 1976, Vol. 36, p. 227.
  5. ↑ a b c Entry on chlorogenic acid. In: Römpp Online . Georg Thieme Verlag, accessed on August 21, 2013.
  6. ^ Franz von Bruchhausen (Ed.): Hager's Handbook of Pharmaceutical Practice . Springer DE, 1949, ISBN 3-540-52688-9 , pp. 7 ( limited preview in Google Book search).
  7. ^ Franz von Bruchhausen (Ed.): Hager's Handbook of Pharmaceutical Practice . Springer DE, 1949, ISBN 3-540-52688-9 , pp. 1044-1050 ( limited preview in Google Book search).
  8. ↑ Artichoke leaves - Cynarae folium (Ph. Eur. 7.0 (01/2011: 1866)). at medizinalpflanze.de.
  9. ^ Franz von Bruchhausen (Ed.): Hager's Handbook of Pharmaceutical Practice . Springer DE, 1949, ISBN 3-540-52688-9 , pp. 21 ( limited preview in Google Book search).
  10. ↑ Linus Pauling Institute, information about micronutrients and coffee from the chemist's point of view ( memento from June 24, 2014 in the Internet Archive ), there working slide "Changes in substances due to roasting" accessed on January 10, 2013.
  11. ↑ a b A. T. Shimoyama, JR Santin, ID Machado: Antiulcerogenic activity of chlorogenic acid in different models of gastric ulcer . In: Naunyn Schmiedebergs Arch. Pharmacol. . 386, No. 1, 2013, pp. 5-14. PMID 23128853 .
  12. ↑ Small inquiry - Why does moss cake turn green? ( Memento from September 28, 2013 in the Internet Archive ) (PDF file; 95 kB) at wdr.de, accessed on January 5, 2013.
  13. ↑ Thomas Schöpke: Chlorogenic acid origin of name. Retrieved on August 21, 2020 (popup page of the website for the lecture on Pharmaceutical Biology , specifically the sub- page Phenylpropane Derivatives , Definition, Classification, Biogenesis, Phenylacrylic Acids ; Thomas Schöpke works at the Institute of Pharmacy at the University of Greifswald ).
  14. ↑ JG Xu, QP Hu, Y. Liu: Antioxidant and DNA-Protective Activities of Chlorogenic Acid Isomers . In: J. Agric. Food Chem . 60, No. 46, 2012, pp. 11625-11630. PMID 23134416 .
  15. ↑ N. Cinkilic, SK Cetintas, T. Zorlu: Radioprotection by two phenolic compounds: Chlorogenic and quinic acid, on X-ray induced DNA damage in human blood lymphocytes in vitro . In: Food and Chemical Toxicology . 2012. PMID 23266271 .
  16. ^ KL Johnston, MN Clifford, LM Morgan: Coffee acutely modifies gastrointestinal hormone secretion and glucose tolerance in humans: glycemic effects of chlorogenic acid and caffeine . In: Am. J. Clin. Nutrit. . 78, No. 4, 2003, pp. 728-733. PMID 14522730 .
  17. ↑ A. Hunyadi, A. Martins, TJ Hsieh: Chlorogenic Acid and Rutin Play a Major Role in the In Vivo Anti-Diabetic Activity of Morus alba Leaf Extract on Type II Diabetic Rats . In: PLOS ONE . 7, No. 11, 2012. PMID 22900702 .
  18. ↑ A. Mubarak, CP Bondonno, AH Liu: Acute effects of chlorogenic acid on nitric oxide status, endothelial function, and blood pressure in healthy volunteers: a randomized trial . In: J Agric Food Chem . 60, No. 36, 2012, pp. 9130-9136. PMID 22900702 .
  19. ↑ HJ Cho, HJ Kang, YJ Kim: Inhibition of platelet aggregation by chlorogenic acid via cAMP and cGMP-dependent manner . In: Blood Coagul. Fibrinolysis . 23, No. 7, 2012, pp. 629-635. PMID 22885765 .
  20. ↑ H. Shi, L. Dong, J. Jiang: Chlorogenic acid reduces liver inflammation and fibrosis through inhibition of toll-like receptor 4 signaling pathway . In: Toxicology . 2012. PMID 23146752 .
  21. ↑ JS Yang, CW Liu, YS Ma: Chlorogenic acid induces apoptotic cell death in U937 leukemia cells through caspase- and mitochondria-dependent pathways . In: In Vivo . 26, No. 6, 2012, pp. 971-978. PMID 23160680 .
  22. ↑ MR Olthof, PC Hollmann, PL Zock: Consumption of high doses of chlorogenic acid, present in coffee, or of black tea increases plasma total homocysteine ​​concentrations in humans . In: Am. J. Clin. Nutr. . 73, No. 3, 2001, pp. 532-538. PMID 11237928 .