| Quinic acid | |
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(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid |
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| Identifiers | |
| CAS number | 77-95-2 |
| PubChem | 6508 |
| ChemSpider | 10246715 |
| ChEBI | CHEBI:17521 |
| ChEMBL | CHEMBL465398 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C7H12O6 |
| Molar mass | 192.17 g/mol |
| Exact mass | 192.063388 |
| Density | 1.35 g/cm³ |
| Melting point |
168 °C, 441 K, 334 °F |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Quinic acid is a cyclitol, a cyclic polyol. 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.
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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.
It is soluble in water and crystallizes in large colorless prisms.[1]
Quinic acid is used as an astringent. By its presence, it serves to distinguish genuine barks.[2]
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.
Quinic acid is also thought to displace binding of the mu opioid receptor antagonist; however, this acid was originally thought to be pharmacologically inactive.
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