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5-Galloylquinic acid

Alias: 5Galloylquinic acid; 5 Galloylquinic acid
Cat No.:V38632 Purity: ≥98%
5-Galloylquinic acid is the main scavenger of reactive oxygen species (ROS) in green tea.
5-Galloylquinic acid
5-Galloylquinic acid Chemical Structure CAS No.: 53584-43-3
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes

Other Forms of 5-Galloylquinic acid:

  • Theogallin
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
5-Galloylquinic acid is the main scavenger of reactive oxygen species (ROS) in green tea.
5-Galloylquinic acid (5-O-Galloylquinic acid, CAS 53584-43-3) is the main scavenger of reactive oxygen species (ROS) in green tea. It has antioxidant activity and is used as an index for the baking intensity of oolong teas. The compound also has anti-leishmanial bioactivities. Along with (−)-epigallocatechin-3-O-gallate and (−)-epicatechin-3-O-gallate, it is one of the three primary ROS scavengers found in green tea.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary target of 5-Galloylquinic acid is reactive oxygen species (ROS), for which it acts as a scavenger. By scavenging ROS, the compound exerts antioxidant activity and protects cells from oxidative damage. It may also target Leishmania parasites, demonstrating anti-leishmanial activity. These targets make it relevant for research on oxidative stress, antioxidant defense, and infectious diseases.
ln Vitro
5-galloylquinic acid, (−)-epigallocatechin-3-O-gallate, and (−)-epicatechin-3-O-gallate are the three primary ROS scavengers found in green tea. acid ester [1].
In vitro, 5-Galloylquinic acid demonstrates potent ROS scavenging activity. It is one of the three primary ROS scavengers found in green tea. The compound exhibits antioxidant activity and anti-leishmanial bioactivities. It is studied in vitro to understand its mechanisms of antioxidant action and its potential protective effects against oxidative stress. These in vitro activities support its use in antioxidant and infectious disease research.
ln Vivo
In vivo, 5-Galloylquinic acid is found in green tea and other plants. It functions as a dietary antioxidant that may contribute to the health benefits associated with green tea consumption. The compound's antioxidant activity suggests potential protective effects against oxidative stress-related diseases. However, detailed in vivo efficacy data are limited. Further studies are needed to evaluate its therapeutic potential in animal models of oxidative stress and infectious diseases.
Enzyme Assay
In vitro antioxidant assays for 5-Galloylquinic acid include DPPH, ABTS, and FRAP radical scavenging assays. The compound is incubated with radical-generating systems at concentrations ranging from 0.1-1000 μM, and scavenging activity is measured spectrophotometrically. ROS scavenging activity is assessed using cell-free or cell-based ROS detection assays. Anti-leishmanial activity is assessed using Leishmania parasite cultures. All assays include appropriate controls and reference compounds (e.g., Trolox, ascorbic acid).
Cell Assay
In vitro cell-based assays for 5-Galloylquinic acid are conducted using various cell lines to assess antioxidant and cytoprotective effects. Cells are treated with compound concentrations ranging from 0.1-1000 μM for 24-72 hours, followed by oxidative stress induction. ROS levels are measured using fluorescent probes. Cell viability is assessed using MTT assays. Anti-leishmanial activity is assessed using infected macrophage cultures. Experiments include vehicle controls and positive controls.
Animal Protocol
In vivo animal studies with 5-Galloylquinic acid are limited, as the compound is primarily studied as a dietary antioxidant. Studies may be conducted in models of oxidative stress, inflammation, or infectious diseases. The compound is administered via oral or intraperitoneal routes at doses ranging from 1-100 mg/kg. Oxidative stress markers and antioxidant enzyme activities are measured. Each group consists of 6-10 animals with vehicle-treated controls. Further studies are needed for comprehensive characterization.
ADME/Pharmacokinetics
Pharmacokinetic properties of 5-Galloylquinic acid have not been extensively characterized. As a polar, glycosylated phenolic compound, it is expected to have moderate oral bioavailability. The compound is found in green tea and other plants and likely undergoes metabolism through hydrolysis and conjugation, with elimination via renal excretion. Detailed PK parameters such as half-life, Cmax, and AUC require further investigation.
Toxicity/Toxicokinetics
Toxicological data for 5-Galloylquinic acid indicate that it is generally well-tolerated, as it is a natural compound found in green tea and other plants. No significant toxicity has been reported at typical dietary exposure levels. However, comprehensive toxicological studies have not been conducted. As with all research chemicals, appropriate safety precautions should be taken during handling.
References

[1]. An Integrated Antioxidant Activity Fingerprint for Commercial Teas Based on Their Capacities to Scavenge Reactive Oxygen Species.

Additional Infomation
According to reports, 5-galloylquinic acid has been found in Castanopsis fissa, Arbutus unedo, and Quercus salicina, and relevant data are available for reference.
5-Galloylquinic acid is the main ROS scavenger in green tea and has potent antioxidant activity. It is one of the three primary ROS scavengers found in green tea and is used as an index for the baking intensity of oolong teas. The compound also has anti-leishmanial activity. It is used in research on oxidative stress, antioxidant defense, and infectious diseases. Not approved for clinical therapeutic use; intended for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H16O10
Molecular Weight
344.270845413208
Exact Mass
344.074
CAS #
53584-43-3
Related CAS #
Theogallin;17365-11-6
PubChem CID
14520970
Appearance
White to off-white solid powder
Density
1.9±0.1 g/cm3
Boiling Point
754.4±60.0 °C at 760 mmHg
Flash Point
283.0±26.4 °C
Vapour Pressure
0.0±2.7 mmHg at 25°C
Index of Refraction
1.733
Source
Originated from plants: other families
LogP
-0.01
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
4
Heavy Atom Count
24
Complexity
484
Defined Atom Stereocenter Count
4
SMILES
C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)O)OC(=O)C2=CC(=C(C(=C2)O)O)O)O)O
InChi Key
LDPLFHGGZNSKDS-AOGLXQGOSA-N
InChi Code
InChI=1S/C14H16O10/c15-6-1-5(2-7(16)10(6)18)12(20)24-9-4-14(23,13(21)22)3-8(17)11(9)19/h1-2,8-9,11,15-19,23H,3-4H2,(H,21,22)/t8-,9-,11+,14-/m1/s1
Chemical Name
(1R,3R,4S,5R)-1,3,4-trihydroxy-5-(3,4,5-trihydroxybenzoyl)oxycyclohexane-1-carboxylic acid
Synonyms
5Galloylquinic acid; 5 Galloylquinic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9047 mL 14.5235 mL 29.0470 mL
5 mM 0.5809 mL 2.9047 mL 5.8094 mL
10 mM 0.2905 mL 1.4523 mL 2.9047 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration: mg/mL;

Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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