Quinic Acid - CAS 77-95-2

D-(-)-Quinic acid, which usually comes from the fruits of Citrus limon (L.) Burm. F, is a cellular metal ion chelator, capable of promoting reactions with metal M(II,III) ions under pH-specific conditions. It is also used in the synthesis of anti-influenza/anti-swine flu medication.

Product Information

Canonical SMILES
O=C([C@@]1(O)C[C@@H](O)[C@H](O)[C@H](O)C1)O
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
Purity
>98%
MDL
MFCD00003864
Physical State
Solid
Appearance
Powder
Storage
Sealed in dry. Room temperature.
Boiling Point
438.4 ℃ / 760 mmHg
Melting Point
166-168 ℃
Optical Activity
−43.9°( c = 11.2 in water)
TSCA
No
WGK Germany
3

Safety Information

Signal Word
Warning
Precautionary Statement
P280 - P262 - P305 - P351 - P338
Hazard Statements
H315 - H317 - H319 - H335

Reference Reading

1.Enantioseparation of DL-isocitric acid by a chiral ligand exchange CE with Ni(II)-D-quinic acid system.
Kodama S;Taga A;Yamamoto A;Ito Y;Honda Y;Suzuki K;Yamashita T;Kemmei T;Aizawa S Electrophoresis. 2010 Oct;31(21):3586-91. doi: 10.1002/elps.201000320.
The ratio of citric acid to D-isocitric acid can be used to distinguish authentic and adulterated fruit juices. To separate DL-isocitric acid enantiomers, we used ligand exchange CE. D-Quinic acid was used as a chiral selector ligand and Mn(II), Fe(III), Co(II), Ni(II), Cu(II), and Zn(II) ions were used as the central ions of the chiral selector in the BGE. DL-Isocitric acid was found to be enantioseparated with the above metal ions except for Mn(II) ion. The optimum running conditions for the analysis of D- and L-isocitric acids along with citric acid, an isomer of isocitric acid, were found to be a BGE (pH 5.0) containing 30% ACN, 20 mM acetic acid, 20 mM NiSO(4), and 80 mM D-quinic acid. Under these conditions, DL-isocitric and citric acids in fruit juices were analyzed successfully.
2.Comprehensive 3-year study of the phenolic profile of Moroccan monovarietal virgin olive oils from the Meknès region.
Bajoub A;Hurtado-Fernández E;Ajal el A;Ouazzani N;Fernández-Gutiérrez A;Carrasco-Pancorbo A J Agric Food Chem. 2015 May 6;63(17):4376-85. doi: 10.1021/jf506097u. Epub 2015 Apr 22.
The phenolic fraction of monovarietal virgin olive oils (VOOs) from the main Moroccan cultivar Picholine marocaine (142 samples from three different subareas of the Meknès region) was studied over three consecutive crop seasons (2011, 2012, and 2013) using a powerful LC-MS methodology. First, LC-ESI-TOF MS was used to get a comprehensive characterization of the phenolic fraction; afterward, LC-ESI-IT MS was utilized for further identification (MS/MS experiments) and quantitation purposes. A total of 28 phenolic compounds (and quinic acid) were determined, revealing the complex profile of Meknès VOO, composed, in order of abundance, by secoiridoids, phenolic alcohols, lignans, flavonoids, and phenolic acids. Tukey's test was applied to ascertain possible significant intraregional and/or interannual variations of the phenolic content of the Meknès VOOs under study. Results showed that the content of phenolic compounds was mainly related to the crop season.
3.Identification of phenolic compounds, antioxidant activity and anti-cancer effects of the extract obtained from the shoots of Ornithogalum narbonense L.
Koyuncu I;Gönel A;Akdağ A;Yilmaz MA Cell Mol Biol (Noisy-le-grand). 2018 Jan 31;64(1):75-83. doi: 10.14715/cmb/2018.64.1.14.
This study aimed to examine the anti-cancer and antioxidant properties and identify the phenolic content of methanolic extract obtained from the shoots of the Ornithogalum narbonense L. (OR) species, which is used for folk-medicine and food in the Sanliurfa region of Turkey. The antioxidant activity of the extract was investigated using total phenolics, flavonoids, ABTS and CUPRAC methods. Phenolic component analysis of the plant extract was performed by LC-MS/MS. The anti-cancer property of OR extract was investigated on human colon (DLD-1), endometrium (ECC-1) cancer cells and embryonic kidney (HEK-293) cells. Cytotoxic effects were defined with MTT, apoptotic activity with DNA fragmentation ELISA and AO/EB fluorescent staining, the genotoxic effect with the comet assay and the intracellular oxidative status with TAS and TOS methods. As a result of the study, it was determined that OR extract showed an antioxidant effect, and as a result of the content analysis made with LC-MS/MS, phenolic components were determined, the most abundant being cosmosiin, followed by cinnamic acid, p-coumaric acid and quinic acid. OR extract showed cytotoxic activity on DLD-1 and ECC-1 cancer cells, while the cytotoxic effect on HEK-293 cells was determined to be low.
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Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

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