-Catechin gallate Chemical Structure.png)
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) |
Biological Activity
| Targets |
Inhibits COX-1 and COX-2 enzyme activities. Inhibits the gene expression of matrix metalloproteinase-9 (MMP-9) in macrophage-differentiated HL-60 myeloid leukemia cells. Inhibits the activity of various proteasomes (multicatalytic proteases). Directly interacts with DNA oligomers. [1] |
| 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]. (-)-Catechin gallate exhibits cytotoxicity towards various human oral cavity-derived cell lines. The sensitivity sequence for a 3-day exposure is: immortalized gingival epithelioid S-G cells > tongue squamous carcinoma CAL27 cells > salivary gland squamous carcinoma HSG cells > normal gingival HGF-1 fibroblasts. The midpoint cytotoxicity (NR₅₀) values for a 3-day exposure to CG were 58 µM for S-G cells, 62 µM for CAL27 cells, 90 µM for HSG cells, and 132 µM for HGF-1 fibroblasts. [1] In S-G cells, the cytotoxicity of a panel of green tea catechins follows the sequence: CG, epicatechin gallate (ECG) > epigallocatechin gallate (EGCG) > epigallocatechin (EGC) > epicatechin (EC), catechin (C). The NR₅₀ values for a 3-day exposure in S-G cells were 58 µM for CG and 36 µM for ECG. [1] Cytotoxicity is time-dependent. For S-G cells, the NR₅₀ values were 127 µM, 67 µM, and 58 µM for 1-, 2-, and 3-day exposures, respectively. [1] Cytotoxicity is not primarily due to oxidative stress. CG is a poor generator of H₂O₂ in culture medium (94 ± 2.3 µmol/L after 3h incubation with 250 µM CG). Intracellular glutathione (GSH) levels were unaffected by CG exposure, and co-incubation with catalase did not ameliorate CG-induced cytotoxicity. [1] CG alone did not induce lipid peroxidation but enhanced Fe²⁺-induced lipid peroxidation in S-G cells. [1] CG induces apoptosis in S-G cells, as evidenced by morphological changes (chromatin condensation, membrane blebbing) observed with acridine orange staining and confirmed by the TUNEL assay. [1] Apoptosis induced by CG appears to be caspase-independent, as no caspase-3 activity was detected in treated cells, and agarose gel electrophoresis showed a DNA smear rather than internucleosomal DNA fragmentation ("DNA laddering"). [1] |
| Cell Assay |
Cell Proliferation/Cytotoxicity Assay (Neutral Red Uptake): Cells were seeded in 96-well plates at different densities depending on exposure duration. After incubation, growth medium was replaced with exposure medium containing varying concentrations of CG or other catechins. After 1-3 days, cell viability was assessed. The medium was removed and replaced with Neutral Red (NR) working solution (0.04 mg/mL in exposure medium) for 1 hour. Cells were then washed, fixed with a formalin-CaCl₂ solution, and the incorporated dye was released with an acetic acid-ethanol solution. Absorbance was measured at 540 nm. Cytotoxicity was expressed as percentage of control, and midpoint cytotoxicity (NR₅₀) values were calculated. [1] Intracellular Glutathione (GSH) Assay: Confluent cells in 6-well plates were treated with CG in PBS for 3 hours. Cells were lysed with Triton X-100, and proteins were precipitated with sulfosalicylic acid. After centrifugation, GSH in the acid-soluble extract was determined by its reaction with 5,5'-dithiobis(2-nitrobenzoic acid) (DTNB). The formation of the yellow chromagen (5-thio-2-nitrobenzoic acid) was measured at 412 nm, and GSH concentration was calculated using a standard curve. [1] Hydrogen Peroxide (H₂O₂) Assay (FOX Method): Exposure medium amended with CG was incubated at room temperature. The FOX reagent was added, and after further incubation and centrifugation, the absorbance of the supernatant was measured at 595 nm. The assay kit used was specific for H₂O₂ generated in the cell culture medium. [1] Lipid Peroxidation Assay: Confluent cells were treated with PBS, Fe²⁺, CG, or both for 4 hours. Trichloroacetic acid was added, cells were scraped, and proteins were precipitated. The supernatant was reacted with thiobarbituric acid in NaOH, heated, and cooled. After centrifugation, the formation of malondialdehyde-thiobarbituric acid adduct (an orange-pink chromagen) was measured at 532 nm. [1] Caspase-3 Activity Assay: S-G cells were treated with CG with or without a pan-caspase inhibitor. Cells were lysed, and lysates were incubated with the caspase-3 substrate DEVD-pNA. Absorbance was read at 410 nm after incubation. [1] Agarose Gel Electrophoresis for DNA Fragmentation: Cells treated with CG were lysed in a digestion buffer with proteinase K and RNase. Extracted DNA was mixed with loading dye, run on a 2% agarose gel, stained with ethidium bromide, and visualized under UV light. [1] Microscopy for Apoptosis Detection (Acridine Orange & TUNEL): Cells grown on coverslips were treated with CG, fixed, and stained with acridine orange. Apoptotic cells were identified by fluorescence microscopy based on chromatin condensation and nuclear fragmentation. Apoptosis was also confirmed using a TUNEL kit according to the manufacturer's instructions, which labels free 3'-ends of broken DNA strands. [1] |
| Toxicity/Toxicokinetics |
The study primarily assesses in vitro cytotoxicity, not classical toxicity parameters. Cytotoxicity varies by cell type, with normal human gingival fibroblasts (HGF-1) being less sensitive (NR₅₀ = 132 µM for 3-day exposure) than immortalized or cancerous oral cell lines. [1] Cytotoxicity was not due to acute oxidative stress or a decrease in intracellular glutathione. [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. (-)-Catechin gallate is a minor polyphenolic constituent of green tea. [1] Its biological and cytotoxic activities are very similar to its epimer, epicatechin gallate (ECG). Both are poor generators of H₂O₂ compared to EGCG, and their cytotoxicity does not appear to be mediated primarily by oxidative stress. [1] The study suggests that CG induces apoptosis in sensitive cells via a caspase-independent pathway. [1] The research supports the idea that minor tea catechins like CG may contribute to the overall chemopreventive effects of green tea consumption, particularly for oral health, as the oral cavity is exposed to high concentrations of tea polyphenols during consumption. [1] |
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 |