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)

CHEBI:17521^Y

10246715^Y

ECHA InfoCard

058C04BGYI^Y

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

C₇H₁₂O₆

192.17 g/mol

1.35 g/cm³

168 °C (334 °F; 441 K)

Hazards

NFPA 704

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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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 1806 by French pharmacist Nicolas Vauquelin^[1] and further reactions from this acid to synthesize other compounds were studied by German chemist Eduard Lautemann in 1863.

Characteristics

It is soluble in water and crystallizes in large colorless prisms.^[2]

Industrial applications

Quinic acid is used as an astringent. 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 Naltrexone, even though this acid was originally thought to be pharmacologically inactive.

References

↑ L. N. Vauquelin (1806) "Expériences sur les diverses espèces de Quinquina" (Experiments on various species of Quinquina), Annales de Chimie, 59 : 113-169. Quinic acid is named on p. 167. From p. 167: "Concluons donc que cet acide est véritablement différent de tous ceux qui sont connus maintenant, et donnons-lui le nom d'acide kinique du mot quinquina, … " (Let us thus conclude that this acid is truly different from all those that are now known, and let us give it the name of quinic acid from the word quinquina, … )
↑ Gilman, D. C.; Thurston, H. T.; Colby, F. M., eds. (1905). "Kinic acid". New International Encyclopedia (1st ed.). New York: Dodd, Mead.
↑ Santos, Sónia A. O.; Freire, Carmen S. R.; Domingues, M. Rosário M.; Silvestre, Armando J. D.; Neto, Carlos Pascoal (2011). "Characterization of Phenolic Components in Polar Extracts of Eucalyptus globulus Labill. Bark by High-Performance Liquid Chromatography–Mass Spectrometry". Journal of Agricultural and Food Chemistry. 59 (17): 9386–93. doi:10.1021/jf201801q. PMID 21761864.

"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.
Ripley, George; Dana, Charles A., eds. (1879). "Kinic Acid". The American Cyclopædia.

Types of hydrolysable tannins

Carbohydrates	Glucose Quinic acid Shikimic acid

Phenolic	gallic acid \| Ellagic acid \| Vanillic acid

Types	Ellagitannins Gallotannins

unclassified	1,2-di-O-galloyl-3-O-digalloyl-4,6-O-(S)-hexa- hydroxydiphenoy-β-D-glucose 2,3-(S)-Hexahydroxydiphenoyl-D-glucose Alienanin B Alunusnin A Aromatinin A Balanophotannin D, E, F and G Burkinabin A, B and C Castavaloninic acid Cinchotannic acid Cocciferin D2 Emblicanins (Emblicanin A and Emblicanin B) Euprostin A Flavogallonic acid Flavogallonic acid dilactone Heterophylliin D Helioscopin A (1,6-(S)-hexahydroxydiphenoyl-2,4-(R)-elaeocarpusinoyl-3-O-galloyl-β-D-glucose) Helioscopin B (1,3,6-tri-O-galloyl-2,4-(R)-elaeocarpusinoyl-β-D-glucose) Helioscopinin A (1,6-(S)-hexahydroxydiphenoyl-2,4-(S)-dehydrohexahydroxydiphenoyl-3-O-galloyl-β-D-glucose) Helioscopinin B (1,6-(S)-hexahydroxydiphenoyl-3-O-galloyl-β-D-glucose) Hipophaenin D Isostrictinin Kinotannic acid Platycaryanin A Rugosin C, D and F Squarrosanin A Strictinin Syzyginin A Tannic acid Tellimagrandin I Tercatin Tergallagin Vescalin Vescavaloneic acid/Castavaloneic acid

Other	Tannin sources Tannate

Authority control	GND: 4147685-2

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