Quinic acid

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Quinic acid
Quinic acid Quinic acid
Identifiers
CAS number 77-95-2 YesY
PubChem 6508
ChemSpider 10246715 YesY
ChEBI CHEBI:17521 YesY
ChEMBL CHEMBL465398 YesY
Jmol-3D images Image 1
Properties
Molecular formula 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
Except where noted otherwise, 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[edit]

This substance was isolated for the first time in the 1800s by French pharmacist Nicolas Vauquelin and further reactions from this acid to synthesize other compounds were studied by German chemist E. Lautemann in 1863.

Characteristics[edit]

It is soluble in water and crystallizes in large colorless prisms.[1]

Industrial applications[edit]

Quinic acid is used as an astringent. By its presence, it serves to distinguish genuine barks.[2] It can be found in the bark of Eucalyptus globulus.[3]

Pharmaceutical uses[edit]

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; however, this acid was originally thought to be pharmacologically inactive.

References[edit]

  1. ^ Wikisource-logo.svg "Kinic acid". New International Encyclopedia. 1905. 
  2. ^ Wikisource-logo.svg "Kinic Acid". The American Cyclopædia. 1879. 
  3. ^ 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. 

Further reading[edit]