Quinic acid CAS NO.77-95-2

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General tips：For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
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Chemical Properties of D-(-)-Quinic acid

Source of D-(-)-Quinic acid

The fruits of Citrus limon (L.) Burm. f.

Biological Activity of D-(-)-Quinic acid

Protocol of D-(-)-Quinic acid

Preparing Stock Solutions of D-(-)-Quinic acid

References on D-(-)-Quinic acid

Regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from D-(-)-quinic acid.[Pubmed:22508330]

Molecules. 2012 Apr 16;17(4):4498-507.

Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-(-)-Quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide.

Expeditious synthesis of tri- and tetrahydroxyazepanes from D-(-)-quinic acid as potent glycosidase inhibitors.[Pubmed:17480095]

J Org Chem. 2007 May 25;72(11):4258-61.

Several new stereoisomers of 3,4,6-trihydroxyazepanes and 7-hydroxymethyl-3,4,5-trihydroxyazepanes as well as known 3,4,5-trihydroxyazepanes were synthesized as potent glycosidase inhibitors from D-(-)-Quinic acid in an efficient manner. The key step employs dihydroxylation of protected chiral 1,4,5-cyclohex-2-enetriols under RuCl3/NaIO4/phosphate buffer (pH 7) condition, followed by reductive amino cyclization. We found the choice of an appropriate protecting group to C1-OH of chiral 1,4,5-cyclohex-2-enetriols would increase the yields of cyclization. The preliminary biological data indicate some of these azepanes possess potent inhibition against alpha-mannosidase and alpha-fucosidase.

Heptanuclear antiferromagnetic Fe(III)-D-(-)-quinato assemblies with an S = 3/2 ground state-pH-specific synthetic chemistry, spectroscopic, structural, and magnetic susceptibility studies.[Pubmed:24266671]

Inorg Chem. 2013 Dec 16;52(24):13849-60.

Iron is an essential metal ion with numerous roles in biological systems and advanced abiotic materials. D-(-)-Quinic acid is a cellular metal ion chelator, capable of promoting reactions with metal M(II,III) ions under pH-specific conditions. In an effort to comprehend the chemical reactivity of well-defined forms of Fe(III)/Fe(II) toward alpha-hydroxycarboxylic acids, pH-specific reactions of: (a) [Fe3O(CH3COO)6(H2O)3].(NO3).4H2O with D-(-)-Quinic acid in a molar ratio 1:3 at pH 2.5 and (b) Mohr's salt with D-(-)-Quinic acid in a molar ratio 1:3 at pH 7.5, respectively, led to the isolation of the first two heptanuclear Fe(III)-quinato complexes, [Fe7O3(OH)3(C7H10O6)6].20.5H2O (1) and (NH4)[Fe7(OH)6(C7H10O6)6].(SO4)2.18H2O (2). Compounds 1 and 2 were characterized by analytical, spectroscopic (UV-vis, FT-IR, EPR, and Mossbauer) techniques, CV, TGA-DTG, and magnetic susceptibility measurements. The X-ray structures of 1 and 2 reveal heptanuclear assemblies of six Fe(III) ions bound by six doubly deprotonated quinates and one Fe(III) ion bound by oxido- and hydroxido-bridges (1), and hydroxido-bridges (2), all in an octahedral fashion. Mossbauer spectroscopy on 1 and 2 suggests the presence of Fe(III) ions in an all-oxygen environment. EPR measurements indicate that 1 and 2 retain their structure in solution, while magnetic measurements reveal an overall antiferromagnetic behavior with a ground state S = 3/2. The collective physicochemical properties of 1 and 2 suggest that the (a) nature of the ligand, (b) precursor form of iron, (c) pH, and (d) molecular stoichiometry are key factors influencing the chemical reactivity of the binary Fe(II,III)-hydroxycarboxylato systems, their aqueous speciation, and ultimately through variably emerging hydrogen bonding interactions, the assembly of multinuclear Fe(III)-hydroxycarboxylato clusters with distinct lattice architectures of specific dimensionality (2D-3D) and magnetic signature.

Colonic availability of polyphenols and D-(-)-quinic acid after apple smoothie consumption.[Pubmed:21370449]

Mol Nutr Food Res. 2011 Mar;55(3):368-77.

SCOPE: The aim of this study was to determine the amounts of polyphenols and D-(-)-Quinic acid reaching the ileostomy bags of probands (and thus the colon in healthy humans) after ingestion of apple smoothie, a beverage containing 60% cloudy apple juice and 40% apple puree. METHODS AND RESULTS: Ten healthy ileostomy subjects each ingested 0.7 L of apple smoothie (a bottle). Their ileostomy bags were collected directly before and 1, 2, 4, 6 and 8 h after smoothie consumption, and the polyphenol and D-(-)-Quinic acid contents of the ileostomy fluids were examined using HPLC-DAD and HPLC-MS/MS. The total polyphenol and D-(-)-Quinic acid content of the apple smoothie was determined to be 1955.6+/-124.6 mg/0.7 L, which is very high compared to cloudy apple juices. The most abundant substances found in the ileostomy bags were oligomeric procyanidins (705.6+/-197.9 mg), D-(-)-Quinic acid (363.4+/-235.5 mg) and 5-caffeoylquinic acid (76.7+/-26.8 mg). Overall recovery of ingested polyphenols and D-(-)-Quinic acid in the ileostomy bags was 63.3+/-16.1%. CONCLUSIONS: The amounts of polyphenol and D-(-)-Quinic acids reaching the ileostomy bags are considerably higher after apple smoothie consumption than after the consumption of cloudy apple juice or cider. These results suggest that the food matrix might affect the colonic availability of polyphenols, and apple smoothies could be more effective in the prevention of chronic colon diseases than both cloudy apple juice and apple cider.

Description

D-(-)-Quinic acid is a cyclohexanecarboxylic acid and is implicated in the perceived acidity of coffee.

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