Quinic acid
McGraw-Hill Science & Technology Dictionary:
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quinic acid
(′kwin·ik ′as·əd)
(organic chemistry) C6H7(OH)4COOH·H2O Ether-insoluble, white crystals with acid taste; melts at 162°C; soluble in alcohol, water, and glacial acetic acid; used in medicine. Also known as chinic acid; kinic acid.
Oxford Dictionary of Biochemistry:
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quinic acid
the d enantiomer (1α,3α,4α,5β)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid occurs commonly in plants, either free or as esters (e.g. chlorogenic acid), and may make up as much as 2 — 10% of the dry weight of leaves. It may be formed by the shikimate pathway. Its catabolism to protocatechuic acid has been extensively studied in Aspergillus nidulans and Neurospora crassa.
| quinhydrone electrode, quinhydrone, quinacrine mustard | |
| quinidine, quinine, quinoid |
Wikipedia on Answers.com:
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Quinic acid
| 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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Contents
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History
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.
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]
Pharmaceutical uses
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.
References
- ^ Gilman, Daniel Coit; Peck, Harry Thurston; Colby, Frank Moore (1905). "
Kinic acid". New International Encyclopedia. New York: Dodd, Mead & Company. Wikisource - ^ "Kinic Acid". The American Cyclopædia. 1879.
Further reading
- "Quinic acid - chiral compounds from nature - Buchler quinine plant in Braunschweig,Germany". Quinic acid. http://www.quinine-buchler.com/quinicacid.htm. Retrieved September 5, 2005.
- "Quinic acid". Fast Health. http://www.fasthealth.com/dictionary/q/quinic_acid.php. Retrieved September 5, 2005.
- "History of Xenobiotic Metabolism". History of Xenobiotic Metabolism. Archived from the original on April 12, 2005. http://web.archive.org/web/20050412074846/http://www.issx.org/hisjune.html. Retrieved September 5, 2005.
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McGraw-Hill Science & Technology Dictionary
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Oxford Dictionary of Biochemistry
Oxford University Press. Oxford Dictionary of Biochemistry and Molecular Biology © 1997, 2000, 2006 All rights reserved.
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