Quinic acid is a cyclitol, a cyclic polyol, and a cyclohexanecarboxylic acid. It is a colorless solid that can be extracted from plant sources. Quinic acid is implicated in the perceived acidity of coffee.
Urtica dioica, the European stinging nettle, is another common source.
It is made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee.
History and biosynthesis
This substance was isolated for the first time in 1790 by Germanpharmacist Friedrich Christian Hofmann in Leer from Cinchona.[2] Its transformation into hippuric acid by animal metabolism was studied by German chemist Eduard Lautemann in 1863.[3]
This acid is a versatile chiral starting material for the synthesis of pharmaceuticals.[4] It is a building block in the synthesis of Oseltamivir, which is used to treat influenza A and B.
References
^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. doi:10.1021/jf201801q. PMID 21761864.
^Hofmann: Crell's chemische Annal.1790, II, p. 314, cited in S. Baup: Über die Chinasäure und einige ihrer Verbindungen. In: Annalen der Physik und Chemie1833, p. 64–70 ([1], p. 64, at Google Books).
^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.
^ a b cBarco, Achille; Benetti, Simonetta; De Risi, Carmela; Marchetti, Paolo; Pollini, Gian P.; Zanirato, Vinicio (1997). "D(-)-Quinic Acid: a Chiron Store for Natural Product Synthesis". Tetrahedron: Asymmetry. 8: 3515–3545. doi:10.1016/S0957-4166(97)00471-0.
Further reading
"Quinic acid - chiral compounds from nature - Buchler quinine plant in Braunschweig,Germany". Quinic acid. Retrieved September 5, 2005.
"Quinic acid". Fast Health. Retrieved September 5, 2005.
"History of Xenobiotic Metabolism". Archived from the original on April 12, 2005. Retrieved September 5, 2005.