Chlorogenic acid

Chlorogenic acid
Names
IUPAC name
(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid
Other names
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
327-97-9 YesY
202650-88-2 (E) N
3D model (Jmol) Interactive image
ChEBI CHEBI:16112 N
ChEMBL ChEMBL284616 N
ChemSpider 1405788 YesY
ECHA InfoCard 100.005.751
PubChem 1794427
RTECS number GU8480000
UNII 318ADP12RI (E) N
Properties
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
Safety data sheet 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
0
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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]

Despite the "chloro" of the name, chlorogenic acids contain no chlorine. Instead, 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

Structurally, chlorogenic acid is the ester formed between caffeic acid and the 3-hydroxyl position of L-quinic acid.[4] Isomers of chlorogenic acid include the caffeoyl ester at other hydroxyl sites on the quinic acid ring: 4-O-caffeoylquinic acid (cryptochlorogenic acid or 4-CQA) and 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, and can be found in coffee.[5] There are several isomers, such as 3,4-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid[6] and cynarine (1,5-dicaffeoylquinic acid).

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

Chlorogenic acid is freely soluble in ethanol and acetone.

Natural occurrences

Chlorogenic acid can be found in bamboo Phyllostachys edulis.[7] as well as in many other plants.[8]

Chlorogenic acid can be found in the shoots of Calluna vulgaris (heather).[9]

Presence in food

Chlorogenic acid and the related compounds cryptochlorogenic acid, and neochlorogenic acid were discovered in the leaves of Hibiscus sabdariffa, a popular tea product worldwide.[10] Isomers of chlorogenic acid are found in potatoes.[11] Chlorogenic acid is the most abundant phenolic acid in the flesh of eggplant fruits.[12]

It is one of the major phenolic compounds identified in peach.[13] It is also found in prunes.[14]

It also is one of the phenols found in green coffee bean extract[15] and in green tea.[16]

Food additive

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

Review articles in 2014[17] and 2011[18] report modest blood pressure lowering effects from chlorogenic acid administration. No studies have appeared to assess possible interactions with antihypertensive drugs or advisability in patients being treated for low blood pressure.

Chlorogenic acid is reported to be a chemical sensitizer responsible for human respiratory allergy to certain types of plant materials.[19]

It could be involved in the laxative effect observed in prunes.[14]

References

  1. ↑ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Lignin biosynthesis". Annual Review of Plant Biology. 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". The American Journal of Clinical Nutrition. 78 (4): 728–733. PMID 14522730.
  3. 1 2 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". 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.
  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". Phytochemistry. 4 (3): 527–529. doi:10.1016/S0031-9422(00)86209-3.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ Jalal, Mahbubul A.F.; Read, David J.; Haslam, E. (1982). "Phenolic composition and its seasonal variation in Calluna vulgaris". Phytochemistry. 21 (6): 1397–1401. doi:10.1016/0031-9422(82)80150-7.
  10. ↑ Zhen, Jing; Villani, Thomas S.; Guo, Yue; Qi, Yadong; Chin, Kit; Pan, Min-Hsiung; Ho, Chi-Tang; Simon, James E.; Wu, Qingli (2016). "Phytochemistry, antioxidant capacity, total phenolic content and anti-inflammatory activity of Hibiscus sabdariffa leaves". Food Chemistry. 190: 673–680. doi:10.1016/j.foodchem.2015.06.006.
  11. ↑ Mendel Friedman (1997). "Chemistry, Biochemistry, and Dietary Role of Potato Polyphenols. A Review". Journal of Agricultural and Food Chemistry. 45 (5): 1523–1540. doi:10.1021/jf960900s.
  12. ↑ Influence of Sample Preparation on Assay of Phenolic Acids from Eggplant. Devanand L. Luthria and Sudarsan Mukhopadhyay, J. Agric. Food Chem., 2006, volume 54, issue 1, pages 41–47, doi:10.1021/jf0522457
  13. ↑ Cheng, G. W.; Crisosto, C. H. (September 1995). "Browning Potential, Phenolic Composition, and Polyphenoloxidase Activity of Buffer Extracts of Peach and Nectarine Skin Tissue" (PDF). Journal of the American Society for Horticultural Science. 120 (5): 835–838.
  14. 1 2 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.
  15. ↑ Onakpoya, I; Terry, R; Ernst, E (2011). "The use of green coffee extract as a weight loss supplement: A systematic review and meta-analysis of randomised clinical trials". Gastroenterology Research and Practice. 2011: 1. doi:10.1155/2011/382852. PMC 2943088Freely accessible. PMID 20871849.
  16. ↑ Rio, D. D.; Stalmach, A; Calani, L; Crozier, A (2010). "Bioavailability of Coffee Chlorogenic Acids and Green Tea Flavan-3-ols". Nutrients. 2 (8): 820–833. doi:10.3390/nu2080820. PMC 3257704Freely accessible.
  17. ↑ Onakpoya, I J; Spencer, E A; Thompson, M J; Heneghan, C J (19 June 2014). "The effect of chlorogenic acid on blood pressure: a systematic review and meta-analysis of randomized clinical trials". Journal of Human Hypertension. 29 (2): 77–81. doi:10.1038/jhh.2014.46. PMID 24943289.
  18. ↑ Zhao, Y.; Wang, J.; Ballevre, O.; Luo, H.; Zhang, W. (2011). "Antihypertensive effects and mechanisms of chlorogenic acids". Hypertension Research. 35 (4): 370–4. doi:10.1038/hr.2011.195. PMID 22072103.
  19. ↑ Freedman, Samuel O.; Shulman, Robert; Krupey, John; Sehon, A.H. (1964). "Antigenic properties of chlorogenic acid". The Journal of Allergy and Clinical Immunology. 35 (2): 97–107. doi:10.1016/0021-8707(64)90023-1.
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