Quinic acid

Quinic acid

Chembox new
Name = Quinic acid
ImageFile = Quinic acid.png ImageName = Quinic acid
ImageFile1 = Quinic-acid-3D-balls.png ImageName1 = Quinic acid
IUPACName = (1S,3R,4S,5R)-1,3,4,5-tetrahydroxy-
cyclohexanecarboxylic acid
Section1 = Chembox Identifiers
SMILES = O [C@] 1(C [C@@H] (O) [C@@H]
(O) [C@H] (O)C1)C(O)=O
Section2 = Chembox Properties
Formula = C7H12O6
MolarMass = 192.17 g/mol
Density = 1.35 g/cm³
MeltingPt = 168 °C
BoilingPt = unknown °C

Quinic acid, C7H12O6 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.

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.

Industrial applications

Quinic acid is used as an astringent.

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 recently.

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

*cite web|title=Quinic acid - chiral compounds from nature - Buchler quinine plant in Braunschweig,Germany|work=Quinic acid|url=http://www.quinine-buchler.com/quinicacid.htm|accessmonthday=September 5 |accessyear=2005
*cite web|title=Quinic acid|work=Fast Health|url=http://www.fasthealth.com/dictionary/q/quinic_acid.php|accessmonthday=September 5 |accessyear=2005
*cite web|title=History of Xenobiotic Metabolism|work=History of Xenobiotic Metabolism|url=http://www.issx.org/hisjune.html|accessmonthday=September 5 |accessyear=2005


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Look at other dictionaries:

  • quinic acid — [kwin′ik] n. [< quina (see QUININE) + IC] a colorless, crystalline acid, C6H7 (OH) 4·COOH, prepared from cinchona bark, coffee beans, etc …   English World dictionary

  • quinic acid — ˈkwi]nik , ˈkwī] noun Etymology: quinic from quin + ic 1. : a crystalline acid C6H7(OH)4COOH obtained from cinchona bark, coffee beans, and other plant products and synthetically by hydrolysis of chlorogenic acid; 1,3,4,5 tetrahydroxy cyclohexane …   Useful english dictionary

  • quinic acid — chino rūgštis statusas T sritis chemija formulė (HO)₄C₆H₇COOH atitikmenys: angl. quinic acid rus. хинная кислота ryšiai: sinonimas – 1,3,4,5 tetrahidroksicikloheksankarboksirūgštis …   Chemijos terminų aiškinamasis žodynas

  • quinic acid — l q.; the (−) isomer is an acid found in cinchona bark and elsewhere in plants; 5 dehydroquinic acid is an intermediate in the biosynthesis of l phenylalanine, l tyrosine, and l tryptophan from carbohydrate precursors; q. forms a γ lactone upon… …   Medical dictionary

  • quinic acid — noun A white crystalline acid, tetrahydroxy cyclohexanecarboxylic acid, obtained from cinchona bark and coffee beans; used as an astringent, and in the synthesis of pharmaceuticals …   Wiktionary

  • quinic acid — /kwin ik/, Chem. a white, crystalline, water soluble, solid cyclic compound, C7H12O6, present in cinchona bark, coffee beans, and the leaves of many plants. Also, chinic acid. [1805 15; < Sp quin(a) quinine + IC] * * * …   Universalium

  • quinic acid — /kwɪnɪk ˈæsəd/ (say kwinik asuhd) noun a white crystalline organic acid, C6H7(OH)4COOH.H2O, present in cinchona bark, coffee beans, and the leaves of many plants. {Spanish quin(a) (from Quechua kina bark) + ic} …  

  • Quinic — Quin ic, a. [See {Quinine}, and cf. {Kinic}.] (Chem.) Pertaining to, derived from, or connected with, quinine and related compounds; specifically, designating a nonnitrogenous acid obtained from cinchona bark, coffee, beans, etc., as a white… …   The Collaborative International Dictionary of English

  • Chlorogenic acid — IUPAC name (1S,3R,4R,5R) 3 {[(2Z) 3 (3,4 dihydr …   Wikipedia

  • Caffeic acid — Chembox new Name = Caffeic acid ImageFile = Caffeic acid.svg ImageName = Caffeic acid ImageFile1 = CaffeicAcid3d.png ImageName1 = Caffeic acid IUPACName = 3 (3,4 Dihydroxyphenyl 3,4 Dihydroxy cinnamic acid trans Caffeate 3,4 Dihydroxy trans… …   Wikipedia

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