Quinic acid

Quinic acid
Names
	IUPAC names (1S,3R,4S,5R)-1,3,4,5-tetrahydroxy-; cyclohexanecarboxylic acid
Identifiers
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.000.976
CompTox Dashboard (EPA)	DTXSID70998288 ;
	SMILES O[C@]1(C[C@@H](O)[C@@H]; (O)[C@H](O)C1)C(O)=O;
Properties
Chemical formula	C7H12O6
Molar mass	192.17 g/mol
Density	1.35 g/cm³
Melting point	168 °C
Boiling point	unknown °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox 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.

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.

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

"Quinic acid - chiral compounds from nature - Buchler quinine plant in Braunschweig,Germany". Quinic acid. {{cite web}}: Unknown parameter |accessmonthday= ignored (help); Unknown parameter |accessyear= ignored (|access-date= suggested) (help)
"Quinic acid". Fast Health. {{cite web}}: Unknown parameter |accessmonthday= ignored (help); Unknown parameter |accessyear= ignored (|access-date= suggested) (help)
"History of Xenobiotic Metabolism". History of Xenobiotic Metabolism. {{cite web}}: Unknown parameter |accessmonthday= ignored (help); Unknown parameter |accessyear= ignored (|access-date= suggested) (help)