Quinic acid

Chemical compound From Wikipedia, the free encyclopedia

Quinic acid is an organic compound with the formula (CHOH)3(CH2)2C(OH)CO2H. The compound is classified as a cyclitol, a cyclic polyol, and a cyclohexanecarboxylic acid. It is a colorless solid that can be extracted from plant sources. Quinic acid is implicated in the perceived acidity of coffee, where it occurs around 13% by weight.[3]

Quick facts Names, Identifiers ...
Quinic acid
Quinic acid
Quinic acid
Quinic acid
Quinic acid
Names
IUPAC name
1ʟ-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylic acid [1]
Preferred IUPAC name
(1S,3R,4S,5R)-1,3,4,5-Tetrahydroxycyclohexane-1-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.976 Edit this at Wikidata
UNII
  • 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 checkY
    Key: AAWZDTNXLSGCEK-WYWMIBKRSA-N checkY
  • 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
  • O[C@]1(C[C@@H](O)[C@@H](O)[C@H](O)C1)C(O)=O
Properties
C7H12O6
Molar mass 192.17 g/mol
Density 1.35 g/cm3
Melting point 168 °C (334 °F; 441 K)
Hazards
GHS labelling:
GHS07: Exclamation mark[2]
Warning[2]
H319[2]
P264, P280, P305+P351+P338, P337+P313[2]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Occurrence and preparation

The compound is obtained from cinchona bark, coffee beans, and the bark of Eucalyptus globulus.[4] It is a constituent of the tara tannins.

Urtica dioica, the European stinging nettle, is another common source.[5]

It is made synthetically by hydrolysis of chlorogenic acid.

History and biosynthesis

Shikimic acid, biosynthetic precursor to aromatic amino acids, is a close relative of quinic acid.

This substance was isolated for the first time in 1790 by German pharmacist Friedrich Christian Hofmann in Leer from Cinchona.[6] Its transformation into hippuric acid by animal metabolism was studied by German chemist Eduard Lautemann in 1863.[7]

Its biosynthesis begins with the transformation of glucose into erythrose 4-phosphate. This four-carbon substrate is condensed with phosphoenol pyruvate to give the seven-carbon 3-deoxy-D-arabinoheptulosonate 7-phosphate (DAHP) by the action of a synthase. Two subsequent steps involving dehydroquinic acid synthase and a dehydrogenase afford the compound.[8]

Derived bicyclic lactones are called quinides. One example is 4-caffeoyl-1,5-quinide.

Dehydrogenation and oxidation of quinic acid affords gallic acid.[8]

Applications and medicinal activity

Quinic acid is used as an astringent.

This acid is a versatile chiral starting material for the synthesis of pharmaceuticals.[8] It is a building block in the synthesis of oseltamivir, which is used to treat influenza A and B.

References

Further reading

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