Quinic acid

Quinic acid

Names
IUPAC name (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
Identifiers
CAS Number	77-95-2 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17521 Y
ChEMBL	ChEMBL465398 Y
ChemSpider	10246715 Y
ECHA InfoCard	100.000.976
PubChem	6508
UNII	058C04BGYI Y
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
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 (334 °F; 441 K)
Hazards
NFPA 704	0 0 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
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.

This substance was isolated for the first time in 1806 by French pharmacist Nicolas Vauquelin and further reactions from this acid to synthesize other compounds were studied by German chemist Eduard Lautemann in 1863.

It is soluble in water and crystallizes in large colorless prisms.

Quinic acid is used as an astringent. It can be found in the bark of Eucalyptus globulus.

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 Naltrexone, even though this acid was originally thought to be pharmacologically inactive.