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5-Galloylquinic acid

CAS# 53584-43-3

5-Galloylquinic acid

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Quality Control of 5-Galloylquinic acid

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Chemical structure

5-Galloylquinic acid

3D structure

Chemical Properties of 5-Galloylquinic acid

Cas No. 53584-43-3 SDF Download SDF
PubChem ID 14520970 Appearance Powder
Formula C14H16O10 M.Wt 344.3
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1R,3R,4S,5R)-1,3,4-trihydroxy-5-(3,4,5-trihydroxybenzoyl)oxycyclohexane-1-carboxylic acid
SMILES C1C(C(C(CC1(C(=O)O)O)OC(=O)C2=CC(=C(C(=C2)O)O)O)O)O
Standard InChIKey LDPLFHGGZNSKDS-AOGLXQGOSA-N
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.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 5-Galloylquinic acid

The leaves of Camellia sinensis.

Biological Activity of 5-Galloylquinic acid

Description5-Galloylquinic acid as an index for the baking intensity of oolong teas. It has antioxidant activity.
TargetsROS
In vitro

Relative content of gallic acid over 5-galloylquinic acid as an index for the baking intensity of oolong teas.[Reference: WebLink]

Journal of Food and Drug Analysis, 2017,26(2):609-619.


METHODS AND RESULTS:
Phenolic compounds in a series of old oolong teas prepared by baking annually were monitored and compared. The results showed that the relative content of gallic acid over 5-Galloylquinic acid was subsequently elevated during this preparatory process. To reveal the effect was mainly resulted from baking or aging, two sets of oolong teas were collected and examined; one set was generated from fresh oolong tea via continually daily baking and the other set was composed of aged oolong teas with no or light baking in the storage period. The relative content of gallic acid over 5-Galloylquinic acid was observed to be subsequently elevated when oolong tea was continually baked at 90, 100, 110, and 120 °C for 8 h day after day. In contrast, the relative contents of gallic acid over 5-Galloylquinic acid in aged oolong teas with no or light baking were found to be similar to or slightly higher than that in fresh oolong tea.
CONCLUSIONS:
The results suggest that the relative content of gallic acid over 5-Galloylquinic acid seems to be a suitable index for the baking intensity of oolong tea in different preparations.

Protocol of 5-Galloylquinic acid

Structure Identification
Food Chemistry, 2017, 237.

An integrated antioxidant activity fingerprint for commercial teas based on their capacities to scavenge reactive oxygen species.[Reference: WebLink]

An integrated antioxidant activity fingerprint, based on on-line screening methods for three reactive oxygen species (ROS: superoxide anion radical, hydrogen peroxide, and hydroxyl radical) was developed to comprehensively evaluate the quality of 12 batches of commercial tea.
METHODS AND RESULTS:
High-performance liquid chromatography (HPLC) coupled with a chemiluminescent detector was used to determine the antioxidant characteristics of a selection of teas as bioactivity fingerprints. An HPLC–electrospray ionization–mass spectrometry analysis was used to determine the chemical profiles of the teas in the chromatographic fingerprints. All of the green teas (S01–S08) were better scavengers of the three ROS compared to the oolong teas (S09–S12). The main scavengers of the three ROS in green tea were 5-Galloylquinic acid, (−)-epigallocatechin-3-O-gallate, and (−)-epicatechin-3-O-gallate, whereas in oolong tea, they were (−)-epigallocatechin-3-O-gallate and (−)-epigallocatechin.
CONCLUSIONS:
This study demonstrates that comprehensive fingerprinting is a potentially meaningful method for evaluating the quality of food products.

5-Galloylquinic acid Dilution Calculator

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5-Galloylquinic acid Molarity Calculator

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Preparing Stock Solutions of 5-Galloylquinic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9044 mL 14.5222 mL 29.0444 mL 58.0889 mL 72.6111 mL
5 mM 0.5809 mL 2.9044 mL 5.8089 mL 11.6178 mL 14.5222 mL
10 mM 0.2904 mL 1.4522 mL 2.9044 mL 5.8089 mL 7.2611 mL
50 mM 0.0581 mL 0.2904 mL 0.5809 mL 1.1618 mL 1.4522 mL
100 mM 0.029 mL 0.1452 mL 0.2904 mL 0.5809 mL 0.7261 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 5-Galloylquinic acid

Physiologic Medium Rewires Cellular Metabolism and Reveals Uric Acid as an Endogenous Inhibitor of UMP Synthase.[Pubmed:28388410]

Cell. 2017 Apr 6;169(2):258-272.e17.

A complex interplay of environmental factors impacts the metabolism of human cells, but neither traditional culture media nor mouse plasma mimic the metabolite composition of human plasma. Here, we developed a culture medium with polar metabolite concentrations comparable to those of human plasma (human plasma-like medium [HPLM]). Culture in HPLM, relative to that in traditional media, had widespread effects on cellular metabolism, including on the metabolome, redox state, and glucose utilization. Among the most prominent was an inhibition of de novo pyrimidine synthesis-an effect traced to uric acid, which is 10-fold higher in the blood of humans than of mice and other non-primates. We find that uric acid directly inhibits uridine monophosphate synthase (UMPS) and consequently reduces the sensitivity of cancer cells to the chemotherapeutic agent 5-fluorouracil. Thus, media that better recapitulates the composition of human plasma reveals unforeseen metabolic wiring and regulation, suggesting that HPLM should be of broad utility.

Critical Evaluation of NIR and ATR-IR Spectroscopic Quantifications of Rosmarinic Acid in Rosmarini folium Supported by Quantum Chemical Calculations.[Pubmed:28388786]

Planta Med. 2017 Aug;83(12-13):1076-1084.

The present study evaluates the analytical performance of near infrared as well as attenuated total reflection infrared spectroscopy for the determination of the rosmarinic acid content in Rosmarini folium. Therefore, the recorded near infrared and attenuated total reflection infrared spectra of 42 milled Rosmarini folium samples were correlated with reference data (range: 1.138-2.199 rosmarinic acid %) obtained by HPLC analysis. Partial least squares regression models were established as a quantitative multivariate data analysis tool. Evaluation via full cross-validation and test set validation resulted in comparable performances for both techniques: near infrared [coefficient of determination: 0.90 (test set validation); standard error of cross-validation: 0.060 rosmarinic acid %; standard error of prediction: 0.058 rosmarinic acid %] and attenuated total reflection infrared [coefficient of determination: 0.91 (test set validation); standard error of cross-validation: 0.063 rosmarinic acid %; standard error of prediction: 0.060 rosmarinic acid %]. Furthermore, quantum chemical calculations were applied to obtain a theoretical infrared spectrum of rosmarinic acid. Good agreement to the spectrum of pure rosmarinic acid was achieved in the lower wavenumber region, whereas the higher wavenumber region showed less compliance. The knowledge of the vibrational modes of rosmarinic acid was used for the association with the high values of the regression coefficient plots of the established partial least squares regression models.

Application of UV-irradiated Fe(III)-nitrilotriacetic acid (UV-Fe(III)NTA) and UV-NTA-Fenton systems to degrade model and natural occurring naphthenic acids.[Pubmed:28388447]

Chemosphere. 2017 Jul;179:359-366.

Naphthenic acids (NAs) are a highly complex mixture of organic compounds naturally present in bitumen and identified as the primary toxic constituent of oil sands process-affected water (OSPW). This work investigated the degradation of cyclohexanoic acid (CHA), a model NA compound, and natural occurring NAs during the UV photolysis of Fe(III)-nitrilotriacetic acid (UV-Fe(III)NTA) and UV-NTA-Fenton processes. The results indicated that in the UV-Fe(III)NTA process at pH 8, the CHA removal increased with increasing NTA dose (0.18, 0.36 and 0.72 mM), while it was independent of the Fe(III) dose (0.09, 0.18 and 0.36 mM). Moreover, the three Fe concentrations had no influence on the photolysis of the Fe(III)NTA complex. The main responsible species for the CHA degradation was hydroxyl radical (OH), and the role of dissolved O2 in the OH generation was found to be negligible. Real OSPW was treated with the UV-Fe(III)NTA and UV-NTA-Fenton advanced oxidation processes (AOPs). The removals of classical NAs (O2-NAs), oxidized NAs with one additional oxygen atom (O3-NAs) and with two additional oxygen atoms (O4-NAs) were 44.5%, 21.3%, and 25.2% in the UV-Fe(III)NTA process, respectively, and 98.4%, 86.0%, and 81.0% in the UV-NTA-Fenton process, respectively. There was no influence of O2 on the NA removal in these two processes. The results also confirmed the high reactivity of the O2-NA species with more carbons and increasing number of rings or double bond equivalents. This work opens a new window for the possible treatment of OSPW at natural pH using these AOPs.

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