Quinic acid

Quinic acid
IUPAC name (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
Identifiers
CAS number	77-95-2 Y
PubChem	6508
ChemSpider	10246715 Y
ChEBI	CHEBI:17521 Y
ChEMBL	CHEMBL465398 Y
Jmol-3D images	{{#if:O[C@]1(C[C@@H](O)[C@@H](O)[C@H](O)C1)C(O)=O|Image 1
SMILES O[C@]1(C[C@@H](O)[C@@H](O)[C@H](O)C1)C(O)=O
InChI InChI=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 Y Key: AAWZDTNXLSGCEK-WYWMIBKRSA-N Y 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 Key: AAWZDTNXLSGCEK-WYWMIBKRBU
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	0 0 0
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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

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

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

Industrial applications

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

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

Further reading

• "Quinic acid - chiral compounds from nature - Buchler quinine plant in Braunschweig,Germany". Quinic acid. Retrieved September 5, 2005. 
• "Quinic acid". Fast Health. Retrieved September 5, 2005. 
• "History of Xenobiotic Metabolism". History of Xenobiotic Metabolism. Archived from the original on April 12, 2005. Retrieved September 5, 2005.