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(-)-Catechin gallate

Cat No.:V33292 Purity: ≥98%
(-)-Catechin gallate is a trace component of green tea catechin.
(-)-Catechin gallate
(-)-Catechin gallate Chemical Structure CAS No.: 130405-40-2
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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1mg
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10mg
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Product Description
(-)-Catechin gallate is a trace component of green tea catechin. (-)-Catechin gallate inhibits COX-1 and COX-2 activity.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
(-)-Catechin gallate (CG) directly interacts with DNA oligomers and inhibits the activity of COX-1 and COX-2 enzymes, matrix metalloproteinases in macrophage differentiated HL-60 myeloid leukemia cells -9 gene expression, adipocyte uptake by the role of the glucose transporter GLUT4, and the activity of various proteasomes, the multicatalytic proteases responsible for the degradation of most cellular proteins. The relative cytotoxicity of (-)-catechin gallate for 3 days of exposure to malignant CAL27 and HSG cells, immortalized epithelioid SG cells, and normal HGF-1 gingival fibroblasts was evaluated. Concentrations at which toxicity initially occurred (P ≤ 0.01) were: 25 μM (-)-catechin gallate for SG cells, 50 μM (-)-catechin gallate for CAL27 cells, and 50 μM (-)-catechin gallate for HSG cells. 62.5 μM (-)-catechin gallate, and 75 μM (-)-catechin gallate. μM (-)-catechin gallate for HGF-1 fibroblasts. Calculated neutral red (NR50) values after 3 days of exposure to (-)-catechin gallate were: 58 μM for SG cells, 62 μM for CAL27 cells, 90 μM for HSG cells, and HGF-1 Fibrocytes are 132 μM[1].
References

[1]. In vitro cytotoxicity of (-)-catechin gallate, a minor polyphenol in green tea. Toxicol Lett. 2007 Jul 10;171(3):171-80.

Additional Infomation
(-)-catechin-3-O-gallate is a gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of (-)-catechin. It has a role as a metabolite. It is a gallate ester, a polyphenol and a member of flavans. It is functionally related to a (-)-catechin and a gallic acid. It is an enantiomer of a (+)-catechin-3-O-gallate.
(-)-Catechin gallate has been reported in Camellia sinensis, Rheum palmatum, and other organisms with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H18O10
Molecular Weight
442.37232
Exact Mass
442.089
CAS #
130405-40-2
Related CAS #
(+/-)-Catechin Gallate-13C3
PubChem CID
6419835
Appearance
Light yellow to brown solid powder
Density
1.8±0.1 g/cm3
Boiling Point
861.7±65.0 °C at 760 mmHg
Flash Point
305.0±27.8 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.825
LogP
2.67
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
4
Heavy Atom Count
32
Complexity
649
Defined Atom Stereocenter Count
2
SMILES
C1[C@H]([C@@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
InChi Key
LSHVYAFMTMFKBA-CTNGQTDRSA-N
InChi Code
InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21+/m1/s1
Chemical Name
[(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
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)
DMSO : ~100 mg/mL (~226.06 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.65 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (5.65 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.2606 mL 11.3028 mL 22.6055 mL
5 mM 0.4521 mL 2.2606 mL 4.5211 mL
10 mM 0.2261 mL 1.1303 mL 2.2606 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.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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