Quinic acid

Quinic acid
Names
IUPAC name
(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.976
UNII
Properties
C7H12O6
Molar mass 192.17 g/mol
Density 1.35 g/cm3
Melting point 168 °C (334 °F; 441 K)
Hazards
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
0
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Quinic acid is a cyclitol, a cyclic polyol, and a cyclohexanecarboxylic acid. It is a crystalline acid obtained from cinchona bark, coffee beans, and other plant products and made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee. It is a constituent of the tara tannins.

History

This substance was isolated for the first time in 1806 by French pharmacist Nicolas Vauquelin[1] and its transformation into hippuric acid by animal metabolism was studied by German chemist Eduard Lautemann in 1863.[2]

Characteristics

It is soluble in water and crystallizes in large colorless prisms.[3]

Industrial applications

Quinic acid is used as an astringent. It can be found in the bark of Eucalyptus globulus.[4]

Pharmaceutical uses

This acid is a versatile chiral starting material for the synthesis of new pharmaceuticals. A medication for the treatment of influenza A and B strains called Tamiflu has been successfully developed and launched into the market.

Quinic acid is also thought to displace binding of the mu opioid receptor antagonist Naltrexone, even though this acid was originally thought to be pharmacologically inactive.

References

  1. ↑ L. N. Vauquelin (1806) "Expériences sur les diverses espèces de Quinquina" (Experiments on various species of Quinquina), Annales de Chimie, 59 : 113-169. Quinic acid is named on p. 167. From p. 167: "Concluons donc que cet acide est véritablement différent de tous ceux qui sont connus maintenant, et donnons-lui le nom d'acide kinique du mot quinquina, … " (Let us thus conclude that this acid is truly different from all those that are now known, and let us give it the name of quinic acid from the word quinquina, … )
  2. ↑ Lautemann, E. (1863) "Ueber die Reduction der Chinasäure zu Benzoësäure und die Verwandlung derselben in Hippursäure im thierischen Organismus" (On the reduction of quinic acid to benzoic acid and its transformation into hippuric acid in the animal organism), Annalen der Chemie, 125 : 9–13.
  3. ↑  Gilman, D. C.; Peck, H. T.; Colby, F. M., eds. (1905). "Kinic acid". New International Encyclopedia (1st ed.). New York: Dodd, Mead.
  4. ↑ Santos, Sónia A. O.; Freire, Carmen S. R.; Domingues, M. Rosário M.; Silvestre, Armando J. D.; Neto, Carlos Pascoal (2011). "Characterization of Phenolic Components in Polar Extracts of Eucalyptus globulus Labill. Bark by High-Performance Liquid Chromatography–Mass Spectrometry". Journal of Agricultural and Food Chemistry. 59 (17): 9386–93. PMID 21761864. doi:10.1021/jf201801q.

Further reading

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