D-(-)-Quinic acid
D-(-)-Quinic acid is a cellular metal ion chelator, capable of promoting reactions with metal M(II,III) ions under pH-specific conditions. It may possess potent inhibition against alpha-mannosidase and alpha-fucosidase.
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Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to
24 months(2-8C).
Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.
Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Mol Nutr Food Res. 2011 Mar;55(3):368-77.
Colonic availability of polyphenols and D-(-)-quinic acid after apple smoothie consumption.[Pubmed:
21370449]
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.
Inorg Chem. 2013 Dec 16;52(24):13849-60.
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]
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.
METHODS AND RESULTS:
In an effort to comprehend the chemical reactivity of well-defined forms of Fe(III)/Fe(II) toward α-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 Mössbauer) 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. Mössbauer spectroscopy on 1 and 2 suggests the presence of Fe(III) ions in an all-oxygen environment.
CONCLUSIONS:
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,
J Org Chem. 2007 May 25;72(11):4258-61.
Expeditious synthesis of tri- and tetrahydroxyazepanes from D-(-)-quinic acid as potent glycosidase inhibitors.[Pubmed:
17480095]
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.
METHODS AND RESULTS:
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.
CONCLUSIONS:
The preliminary biological data indicate some of these azepanes possess potent inhibition against alpha-mannosidase and alpha-fucosidase.
