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
CAS Number	77-95-2  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17521  Y
ChEMBL	ChEMBL465398  Y
ChemSpider	10246715  Y
ECHA InfoCard	100.000.976
PubChem CID	6508
UNII	058C04BGYI  Y
CompTox Dashboard (EPA)	DTXSID70998288
InChI 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
Chemical formula	C7H12O6
Molar mass	192.17 g/mol
Density	1.35 g/cm3
Melting point	168 °C (334 °F; 441 K)
Hazards
GHS labelling:
Pictograms	[2]
Signal word	Warning [2]
Hazard statements	H319 [2]
Precautionary statements	P264, P280, P305+P351+P338, P337+P313 [2]
NFPA 704 (fire diamond)	0 0 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y  verify  (what is  YN ?) Infobox references

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]

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. Quinic acid is also implicated in the perceived acidity of coffee.

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

1. "Nomenclature of Cyclitols, Recommendations, 1973 – Recommendations – Cyclitols with Groups other than Hydroxyl or Substituted Hydroxyl – I-8. and I-9.2". iupac.qmul.ac.uk. Retrieved 19 March 2025.
2. "D-(−)-Quinic acid Safety Data Sheet". Sigma-Aldrich .
3. Viani, Rinantonio; Petracco, Marino (2007). "Coffee". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a07_315.pub2. ISBN   978-3-527-30385-4.
4. 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. Bibcode:2011JAFC...59.9386S. doi:10.1021/jf201801q. PMID   21761864.
5. Đurović, Saša; Kojić, Ivan; Radić, Danka; Smyatskaya, Yulia A.; Bazarnova, Julia G.; Filip, Snežana; Tosti, Tomislav (8 March 2024). "Chemical Constituents of Stinging Nettle (Urtica dioica L.): A Comprehensive Review on Phenolic and Polyphenolic Compounds and Their Bioactivity". International Journal of Molecular Sciences. 25 (6): 3430. doi: 10.3390/ijms25063430 . ISSN   1422-0067. PMC   10970493 . PMID   38542403.
6. Hofmann: Crell's chemische Annal.1790, II, p. 314, cited in S. Baup: Über die Chinasäure und einige ihrer Verbindungen. In: Annalen der Physik und Chemie1833, p. 64–70 ( , p. 64, at Google Books).
7. Lautemann, E. (1863) "Ueber die Reduction der Chinasäure zu Benzoësäure und die Verwandlung derselben in Hippursäure im thierischen Organismus" (On the reduction of quinic acid to benzoic acid and its transformation into hippuric acid in the animal organism), Annalen der Chemie, 125 : 9–13.
8. Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Marchetti, Paolo; Pollini, Gian P.; Zanirato, Vinicio (1997). "D(-)-Quinic Acid: a Chiron Store for Natural Product Synthesis". Tetrahedron: Asymmetry. 8: 3515–3545. doi:10.1016/S0957-4166(97)00471-0.

Further reading

• "Quinic acid - chiral compounds from nature - Buchler quinine plant in Braunschweig, Germany". Quinic acid. Archived from the original on March 6, 2001. Retrieved September 5, 2005.
• "Quinic acid". Fast Health. Retrieved September 5, 2005.
• "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 .