Quinic acid

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title: "Quinic acid" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["quinic-acid", "cyclohexanecarboxylic-acids", "tetrols"] topic_path: "general/quinic-acid" source: "https://en.wikipedia.org/wiki/Quinic_acid" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 470455534 | Name = Quinic acid | ImageFileL1 = Quinic acid flat.svg | ImageNameL1 = Quinic acid | ImageFileR1 = (−)-quinic-acid-from-xtal-3D-bs-17.png | ImageNameR1 = Quinic acid | IUPACName = 1ʟ-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylic acid | PIN = (1S,3R,4S,5R)-1,3,4,5-Tetrahydroxycyclohexane-1-carboxylic acid |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 10246715 | ChEMBL_Ref = | ChEMBL = 465398 | InChI = 1/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1 | InChIKey = AAWZDTNXLSGCEK-WYWMIBKRBU | StdInChI_Ref = | StdInChI = 1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = AAWZDTNXLSGCEK-WYWMIBKRSA-N | CASNo_Ref = | CASNo = 77-95-2 | UNII_Ref = | UNII = 058C04BGYI | PubChem = 6508 | ChEBI_Ref = | ChEBI = 17521 | SMILES = O[C@]1(CC@@HC@@HC@HC1)C(O)=O |Section2={{Chembox Properties | Formula = C7H12O6 | MolarMass = 192.17 g/mol | Density = 1.35 g/cm3 | MeltingPtC = 168 | BoilingPt = |Section3={{Chembox Hazards | NFPA-H = 0 | NFPA-F = 0 | NFPA-R = 0 | GHSPictograms = | GHSSignalWord = Warning | HPhrases = | PPhrases = Quinic acid is an organic compound with the formula . 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. Quinic acid is implicated in the perceived acidity of coffee, where it occurs around 13% by weight.

Occurrence and preparation

The compound is obtained from cinchona bark, coffee beans, and the bark of Eucalyptus globulus. It is a constituent of the tara tannins.

Urtica dioica, the European stinging nettle, is another common source.

It is made synthetically by hydrolysis of chlorogenic acid.

History and biosynthesis

::figure[src="https://upload.wikimedia.org/wikipedia/commons/f/f9/Shikimi.svg" caption="page=64}}). Its transformation into [[hippuric acid]] by animal metabolism was studied by German chemist Eduard Lautemann in 1863.Lautemann, E. (1863) [https://babel.hathitrust.org/cgi/pt?id=uva.x002457962;view=1up;seq=21 "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."] ::

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.

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

Dehydrogenation and oxidation of quinic acid affords gallic acid.

Applications and medicinal activity

Quinic acid is used as an astringent.

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

References

References

  1. "Nomenclature of Cyclitols, Recommendations, 1973 – Recommendations – Cyclitols with Groups other than Hydroxyl or Substituted Hydroxyl – I-8. and I-9.2.".
  2. "D-(−)-Quinic acid Safety Data Sheet".
  3. (2007). "Ullmann's Encyclopedia of Industrial Chemistry".
  4. (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.
  5. (8 March 2024). "Chemical Constituents of Stinging Nettle (Urtica dioica L.): A Comprehensive Review on Phenolic and Polyphenolic Compounds and Their Bioactivity". International Journal of Molecular Sciences.
  6. 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 ({{Google books. hSEAAAAAMAAJ
  7. Lautemann, E. (1863) [https://babel.hathitrust.org/cgi/pt?id=uva.x002457962;view=1up;seq=21 "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.
  8. (1997). "D(-)-Quinic Acid: a Chiron Store for Natural Product Synthesis". Tetrahedron: Asymmetry.

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quinic-acidcyclohexanecarboxylic-acidstetrols