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Quinic acid is an organic compound with the formula (CHOH)3(CH2)2C(OH)CO2H. The compound is classified as a cyclitol, a cyclic polyol, and a cyclohexanecarboxylic acid. It is a colorless solid that can be extracted from plant sources.

Occurrence and preparation

Quinic acid is present in many plants as a caffeoylquinic acid, which are esters of quinic acid with caffeic acids. Esterified with one unit of caffeic acid it forms chlorogenic acid. Esterified with two units of caffeic acid, it forms cynarine.

It is found in Cinchona bark at high concentrations.[3] It is also found in coffee beans and the bark of Eucalyptus globulus.[4] It is a constituent of the tara tannins. Kiwifruit also have a high level of quinic acid (1–2% w/w) as a key component of their flavor.[5] It can also be found in high quantities in the fruit of some accessions of Malus coronaria.[6]

It is made synthetically by hydrolysis of chlorogenic acid.

History and biosynthesis

Shikimic acid, biosynthetic precursor to aromatic amino acids, is a close relative of quinic acid.

This substance was isolated for the first time in 1790 by German pharmacist Friedrich Christian Hofmann in Leer from Cinchona.[7] Its transformation into hippuric acid by animal metabolism was studied by German chemist Eduard Lautemann in 1863.[8]

Its biosynthesis begins with the transformation of glucose into erythrose 4-phosphate. This four-carbon substrate is condensed with phosphoenol pyruvate to give the seven-carbon 3-deoxy-D-arabinoheptulosonate 7-phosphate (DAHP) by the action of a synthase. Two subsequent steps involving dehydroquinic acid synthase and a dehydrogenase afford the compound.[9]

Derived bicyclic lactones are called quinides. One example is 4-caffeoyl-1,5-quinide.

Dehydrogenation and oxidation of quinic acid affords gallic acid.[9]

Applications and medicinal activity

This acid is a versatile chiral starting material for the synthesis of pharmaceuticals.[9] It is a building block in the synthesis of oseltamivir, which is used to treat influenza A and B.

References

  1. ^ “Nomenclature of Cyclitols, Recommendations, 1973 – Recommendations – Cyclitols with Groups other than Hydroxyl or Substituted Hydroxyl – I-8. and I-9.2”. iupac.qmul.ac.uk. Retrieved 19 March 2025.
  2. ^ a b c d “D-(−)-Quinic acid Safety Data Sheet”. Sigma-Aldrich.
  3. ^ “Chemical QUINIC-ACID – Dr. Duke’s Phytochemical and Ethnobotanical Databases”. Archived from the original on January 18, 2026. Retrieved April 22, 2026.
  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. Bibcode:2011JAFC…59.9386S. doi:10.1021/jf201801q. PMID 21761864.
  5. ^ Marsh, Ken B.; Boldingh, Helen L.; Shilton, Rebecca S.; Laing, William A. (2009). “Changes in quinic acid metabolism during fruit development in three kiwifruit species”. Functional Plant Biology. 36. doi:10.1071/fp08240.
  6. ^ Zambiasi, Genny; Solovyev, Pavel; Degasperi, Marta; Busatto, Nicola; Guerra, Walter; Bontempo, Luana; Troggio, Michela; Farneti, Brian; Costa, Fabrizio (2026). “Primary metabolite profiling by NMR reveals the key role of sugars and organic acids in driving the domestication process in apple”. Scientia Horticulturae. 357. doi:10.1016/j.scienta.2026.114681. hdl:10449/95095.
  7. ^ 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 Chemie 1833, p. 64–70 ([1], p. 64, at Google Books).
  8. ^ 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.
  9. ^ a b c Barco, 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