Chlorogenic acid

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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
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[edit]

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]

It should be noted that there is considerable ambiguity about the atom-numbering of chlorogenic acid.[5] The order of numbering of atoms on the quinic acid ring was reversed in 1976 following IUPAC guidelines, with the consequence that 3-CQA became 5-CQA, and 5-CQA became 3-CQA. This article uses the original numbering, which was exclusive prior to 1976, (chlorogenic acid being 3-CQA, while neochlorogenic acid is 5-CQA). Thereafter researchers and manufacturers have been divided, with both numbering systems in use. Even the 1976 IUPAC recommendations are not entirely satisfactory when applied to some of the less common chlorogenic acids.[6][unreliable source?]

Structures having more than one caffeic acid group are called isochlorogenic acids, and can be found in coffee.[7] There are several isomers, such as 3,4-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid[8] and cynarine (1,5-dicaffeoylquinic acid).

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

Chlorogenic acid is freely soluble in ethanol and acetone.

Natural occurrences[edit]

Chlorogenic acid can be found in the bamboo Phyllostachys edulis.[9] as well as in many other plants.[10]

Chlorogenic acid can be found in the shoots of common heather (Calluna vulgaris).[11]

Presence in food[edit]

Chlorogenic acid and the related compounds cryptochlorogenic acid, and neochlorogenic acid have been found in the leaves of Hibiscus sabdariffa, a popular tea product worldwide.[12] Isomers of chlorogenic acid are found in potatoes.[13] Chlorogenic acid is the most abundant phenolic acid in the flesh of eggplants.[14]

It is one of the major phenolic compounds identified in peach.[15] It is also found in prunes.[16]

It also is one of the phenols found in green coffee bean extract[17] and in green tea.[18]

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".[citation needed]

Biological effects[edit]

Review articles in 2011[19] and 2014[20] 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.[21]

It could be involved in the laxative effect observed in prunes.[16]

References[edit]

  1. ^ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Lignin biosynthesis". Annual Review of Plant Biology. 54: 519–546. 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. ^ 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". 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. ^ Ventura, K. (2016). "Unremitting problems with chlorogenic acid nomenclature: a review". Química Nova. 39 (4): 530–533. doi:10.5935/0100-4042.20160063. 
  6. ^ M. N. Clifford and L. Abranko. Some Notes on the Chlorogenic Acids. 1. Numbering and Nomenclature. ResearchGate. doi:10.13140/RG.2.2.22301.31202 2017.
  7. ^ Barnes, H. M.; Feldman, J. R.; White, W. V. (1950). "Isochlorogenic Acid. Isolation from Coffee and Structure Studies". J. Am. Chem. Soc. 72 (9): 4178–4182. doi:10.1021/ja01165a095. 
  8. ^ 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. 
  9. ^ 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): 4646–4652. doi:10.1021/jf010514x. 
  10. ^ Clifford, M. N. (2003). "14. The analysis and characterization of chlorogenic acids and other cinnamates". In Santos-Buelga, C.; Williamson, G. Methods in Polyphenol Analysis. Cambridge: Royal Society of Chemistry. pp. 314–337. ISBN 0-85404-580-5. 
  11. ^ 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. 
  12. ^ 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. 
  13. ^ Friedman, Mendel (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. 
  14. ^ Luthria, Devanand L.; Mukhopadhyay, Sudarsan (2006). "Influence of Sample Preparation on Assay of Phenolic Acids from Eggplant". J. Agric. Food Chem. 54 (1): 41–47. doi:10.1021/jf0522457. 
  15. ^ 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. 
  16. ^ a b Stacewicz-Sapuntzakis, M.; Bowen, P. E.; Hussain, E. A.; Damayanti-Wood, B. I.; Farnsworth, N. R. (2001). "Chemical composition and potential health effects of prunes: a functional food?". Critical Reviews in Food Science and Nutrition. 41 (4): 251–286. doi:10.1080/20014091091814. PMID 11401245. 
  17. ^ 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: 1–6. doi:10.1155/2011/382852. PMC 2943088Freely accessible. PMID 20871849. 
  18. ^ 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. PMID 22254058. 
  19. ^ Zhao, Y.; Wang, J.; Ballevre, O.; Luo, H.; Zhang, W. (2011). "Antihypertensive effects and mechanisms of chlorogenic acids". Hypertension Research. 35 (4): 370–374. doi:10.1038/hr.2011.195. PMID 22072103. 
  20. ^ 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. 
  21. ^ 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.