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Quinic acid

Quinic acid

Chemical name	(1S,3R,4S,5R)-1,3,4,5-tetrahydroxy- cyclohexanecarboxylic acid
Chemical formula	C₇H₁₂O₆
Molecular mass	192.17 g/mol
CAS number	[77-95-2]
Density	1.35 g/cm³
Melting point	168 °C
Boiling point	unknown °C
SMILES	O[C@]1(C[C@@H](O)[C@@H] (O)[C@H](O)C1)C(O)=O
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.

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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.

Industrial applications

Quinic acid is used as an astringent.

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.

References

Quinic acid - chiral compounds from nature - Buchler quinine plant in Braunschweig,Germany. Quinic acid. Retrieved on September 5, 2005.
Quinic acid. Fast Health. Retrieved on September 5, 2005.
History of Xenobiotic Metabolism. History of Xenobiotic Metabolism. Retrieved on September 5, 2005.

Category: Carboxylic acids