Quinic acid

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Quinic acid
Quinic acid
Quinic acid
IUPAC name (1S,3R,4S,5R)-1,3,4,5-tetrahydroxy-
cyclohexanecarboxylic acid
Identifiers
CAS number
SMILES O[C@]1(C[C@@H](O)[C@@H]
(O)[C@H](O)C1)C(O)=O
Properties
Molecular formula C7H12O6
Molar mass 192.17 g/mol
Density 1.35 g/cm³
Melting point

168 °C
Boiling point

unknown °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Quinic acid, C7H12O6 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.

Contents

[edit] History

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

[edit] Industrial applications

Quinic acid is used as an astringent.

[edit] Pharmaceutical uses

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

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

[edit] References

 The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking.