(-)-Gallocatechin gallateCAS# 4233-96-9 |
- Gallocatechin gallate
Catalog No.:BCN6803
CAS No.:5127-64-0
- (-)-Epigallocatechin gallate
Catalog No.:BCN6326
CAS No.:989-51-5
Quality Control & MSDS
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| Cas No. | 4233-96-9 | SDF | Download SDF |
| PubChem ID | 199472 | Appearance | White powder |
| Formula | C22H18O11 | M.Wt | 458.37 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Synonyms | (-)-Gallocatechol gallate | ||
| Solubility | DMSO : ≥ 150 mg/mL (327.25 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | [(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate | ||
| SMILES | C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O | ||
| Standard InChIKey | WMBWREPUVVBILR-NQIIRXRSSA-N | ||
| Standard InChI | InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21+/m1/s1 | ||
| 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. |
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| 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. |
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| 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. | ||
| Description | (-)-Gallocatechin gallate has cancer-preventive activities, it can precipitate cholesterol, decreasee osteoclastogenesis at 20 microM. |
| Targets | NF-κB | mRNA |
| In vitro | Effects of tea catechins, epigallocatechin, gallocatechin, and gallocatechin gallate, on bone metabolism.[Pubmed: 19653629 ]J Agric Food Chem. 2009 Aug 26;57(16):7293-7.
Heat-epimerized tea catechins rich in gallocatechin gallate and catechin gallate are more effective to inhibit cholesterol absorption than tea catechins rich in epigallocatechin gallate and epicatechin gallate.[Pubmed: 14640575]J Agric Food Chem. 2003 Dec 3;51(25):7303-7.It has been known that tea catechins, (-)-epicatechin (1), (-)-epigallocatechin (2), (-)-epicatechin gallate (3), and (-)-epigallocatechin gallate (4) are epimerized to(-)-catechin (5), (-)-gallocatechin (6), (-)-catechin gallate (7), and (-)-Gallocatechin gallate (8), respectively, during retort pasteurization. We previously reported that tea catechins, mainly composed of 3 and 4, effectively inhibit cholesterol absorption in rats.
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| Cell Research | Epigallocatechin gallate and gallocatechin gallate in green tea catechins inhibit extracellular release of Vero toxin from enterohemorrhagic Escherichia coli O157:H7.[Pubmed: 10572924]Biochim Biophys Acta. 1999 Oct 18;1472(1-2):42-50.We studied the effects of six catechin derivatives (catechin, epigallocatechin, epicatechin, epicatechin gallate, epigallocatechin gallate (EGCg) and (-)-Gallocatechin gallate(GCg)) in green tea on the production and extracellular release of Vero toxins (VTs) from enterohemorrhagic Escherichia coli (EHEC) cultured at 37 degrees C for 24 h. EGCg and GCg in the culture medium markedly inhibited extracellular VTs release from EHEC cells into the culture supernatant fluid at concentrations of 0.05 mg/ml or higher, as estimated by both the reversed passive latex agglutination assay and cytotoxic assay using Vero cells. Production and extracellular release of maltose binding protein, a periplasmic protein, into the culture supernatant were also inhibited by EGCg and (-)-Gallocatechin gallate, indicating that their inhibitory effect on release from periplasm into the outer milieu is not specific to VTs, but general to the proteins accumulated in EHEC periplasm. |
(-)-Gallocatechin gallate Dilution Calculator
(-)-Gallocatechin gallate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1816 mL | 10.9082 mL | 21.8164 mL | 43.6329 mL | 54.5411 mL |
| 5 mM | 0.4363 mL | 2.1816 mL | 4.3633 mL | 8.7266 mL | 10.9082 mL |
| 10 mM | 0.2182 mL | 1.0908 mL | 2.1816 mL | 4.3633 mL | 5.4541 mL |
| 50 mM | 0.0436 mL | 0.2182 mL | 0.4363 mL | 0.8727 mL | 1.0908 mL |
| 100 mM | 0.0218 mL | 0.1091 mL | 0.2182 mL | 0.4363 mL | 0.5454 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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(-)-Gallocatechin gallate is the polyphenol isolated from tea, with cancer-preventive activities.
In Vitro:The amount of (-)-Gallocatechin gallate does not differ in leaves of different stages, and the content is relatively low[1]. (−)-gallocatechin gallate in combination with active catechins ((−)-epigallocatechin gallate) has synergistic effects on the induction of apoptosis and inhibition of cell growth for PC-9 cells. (−)-gallocatechin gallate shows inhibitory effect on α-Glucosidase and DPPH, with IC50s of 30.2 μM and 12.2 μg/mL[2].
References:
[1]. Zhang LQ, et al. Accumulation of catechins and expression of catechin synthetic genes in Camellia sinensis at different developmental stages. Bot Stud. 2016 Dec;57(1):31.
[2]. Zhou H, et al. C-geranylated flavanones from YingDe black tea and their antioxidant and α-glucosidase inhibition activities. Food Chem. 2017 Nov 15;235:227-233.
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Effects of tea catechins, epigallocatechin, gallocatechin, and gallocatechin gallate, on bone metabolism.[Pubmed:19653629]
J Agric Food Chem. 2009 Aug 26;57(16):7293-7.
In this study, three tea catechins, epigallocatechin (EGC), gallocatechin (GC), and gallocatechin gallate (GCG), were investigated for their effects on bone metabolism. The effects of the tea catechins on bone formation were evaluated using cultured rat osteoblast-like osteosarcoma cell line UMR-106. EGC stimulated alkaline phosphatase activity significantly at concentrations of 10 and 20 microM. The amount of mineralization also increased significantly with EGC. On another cell culture platform, EGC significantly inhibited osteoclast formations from RAW 264.7 cells upon receptor activation of nuclear factor-kappaB ligand induction on the fourth day of treatment, at a concentration of 10 microM. EGC also dose-dependently inhibited the mRNA expression of tatrate-resistant acid phosphatase. GC and GCG could decrease osteoclastogenesis at 20 microM. The present study illustrated that the tea catechins, EGC in particular, had positive effects on bone metabolism through a double process of promoting osteoblastic activity and inhibiting osteoclast differentiations.
Heat-epimerized tea catechins rich in gallocatechin gallate and catechin gallate are more effective to inhibit cholesterol absorption than tea catechins rich in epigallocatechin gallate and epicatechin gallate.[Pubmed:14640575]
J Agric Food Chem. 2003 Dec 3;51(25):7303-7.
It has been known that tea catechins, (-)-epicatechin (1), (-)-epigallocatechin (2), (-)-epicatechin gallate (3), and (-)-epigallocatechin gallate (4) are epimerized to(-)-catechin (5), (-)-gallocatechin (6), (-)-catechin gallate (7), and (-)-Gallocatechin gallate (8), respectively, during retort pasteurization. We previously reported that tea catechins, mainly composed of 3 and 4, effectively inhibit cholesterol absorption in rats. In this study, the effect of heat-epimerized catechins on cholesterol absorption was compared with tea catechins. Both tea catechins and heat-epimerized catechins lowered lymphatic recovery of cholesterol in rats cannulated in the thoracic duct and epimerized catechins were more effective than tea catechins. The effect of purified catechins on micellar solubility of cholesterol was examined in an in vitro study. The addition of gallate esters of catechins reduced micellar solubility of cholesterol by precipitating cholesterol from bile salt micelles. Compounds 7 and 8 were more effective to precipitate cholesterol than 3 and 4, respectively. These observations strongly suggest that heat-epimerized catechins may be more hypocholesterolemic than tea catechins.
Epigallocatechin gallate and gallocatechin gallate in green tea catechins inhibit extracellular release of Vero toxin from enterohemorrhagic Escherichia coli O157:H7.[Pubmed:10572924]
Biochim Biophys Acta. 1999 Oct 18;1472(1-2):42-50.
We studied the effects of six catechin derivatives (catechin, epigallocatechin, epicatechin, epicatechin gallate, epigallocatechin gallate (EGCg) and gallocatechin gallate (GCg)) in green tea on the production and extracellular release of Vero toxins (VTs) from enterohemorrhagic Escherichia coli (EHEC) cultured at 37 degrees C for 24 h. EGCg and GCg in the culture medium markedly inhibited extracellular VTs release from EHEC cells into the culture supernatant fluid at concentrations of 0.05 mg/ml or higher, as estimated by both the reversed passive latex agglutination assay and cytotoxic assay using Vero cells. Production and extracellular release of maltose binding protein, a periplasmic protein, into the culture supernatant were also inhibited by EGCg and GCg, indicating that their inhibitory effect on release from periplasm into the outer milieu is not specific to VTs, but general to the proteins accumulated in EHEC periplasm.
