(-)-Catechin gallate

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10 Milligram	Negotiable

10 Milligram

Negotiable

Min.Order :10 Milligram
Purity: ≥98%
Payment Terms : T/T

Keywords

(-)-Catechin gallate 130405-40-2 standard supplier in China

Quick Details

Appearance:detailed see specifications
Application:analysis,activity test,Botanical Reference Materials,Standard materials
PackAge:According to the clients requirement.
ProductionCapacity:1|Metric Ton|Day
Storage:Store at 2~8°C
Transportation:by air or by ocean shipping

Superiority:

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers.
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.

Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
E.Traditional Chinese Medicine compounds library

1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
3.Provide various screening libraries and more inhibitor products;
4.Provide separation and structural determination of natural products;
5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries

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.

Details:

Chemical Properties of (-)-Catechin gallate(CG)

Cas No.	130405-40-2
PubChem ID	6419835	Appearance	White-beige powder
Formula	C₂₂H₁₈O₁₀	M.Wt	442.37
Type of Compound	Flavonoids	Storage	Desiccate at -20°C
Synonyms	(-)-Catechin 3-gallate; (-)-Catechin 3-O-gallate
Solubility	DMSO : 100 mg/mL (226.06 mM; Need ultrasonic)
Chemical Name	[(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-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)OC(=O)C4=CC(=C(C(=C4)O)O)O
Standard InChIKey	LSHVYAFMTMFKBA-CTNGQTDRSA-N
Standard InChI	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
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 (-)-Catechin gallate(CG)

The wood of Acacia catechu (L.F.) Willd.

Biological Activity of (-)-Catechin gallate(CG)

Description

(-)-Catechin gallate is a minor constituent in green tea catechins, it inhibits the activity of COX-1 and COX-2 enzymes. Catechin gallate (IC50=53 microM) shows cytotoxicity against the colorectal adenocarcinoma cell line HCT116, it also exhibits strong anti-proliferative and anti-inflammatory activities on pancreatic ductal adenocarcinoma (PDAC) cells. Catechin 3-gallate is a good inhibitor of maltase, with IC50 values of 62 uM, it inhibits both α-glucosidases and rabbit glycogen phosphorylase (GP) in vitro and in cell culture, would contribute to the protection or improvement of type 2 diabetes.

Targets

Caspase | IL Receptor | CDK | TNF-α | NF-kB

In vitro

In vitro cytotoxicity of (-)-catechin gallate, a minor polyphenol in green tea.[Pubmed: 17606338]

Toxicol Lett. 2007 Jul 10;171(3):171-80.

The cytotoxicity of (-)-Catechin gallate(CG), a minor polyphenolic constituent in green tea, towards cells derived from tissues of the human oral cavity was studied.
METHODS AND RESULTS:
The sequence of sensitivity to (-)-Catechin gallate(CG) was: immortalized epithelioid gingival S-G cells>tongue squamous carcinoma CAL27 cells>salivary gland squamous carcinoma HSG cells>>normal gingival HGF-1 fibroblasts. Further studies focused on S-G cells, the cells most sensitive to (-)-Catechin gallate(CG). The response of the S-G cells to (-)-Catechin gallate(CG) was dependent on the length of exposure, with midpoint cytotoxicity values of 127, 67 and 58muM (-)-Catechin gallate(CG) for 1-, 2- and 3-day exposures, respectively. The sequence of sensitivity of the S-G cells to various green tea catechins was characterized as follows: (-)-Catechin gallate(CG), epicatechin gallate (ECG)>epigallocatechin gallate (EGCG)>epigallocatechin (EGC)>>epicatechin (EC), catechin (C). The cytotoxicity of (-)-Catechin gallate(CG), apparently, was not due to oxidative stress as it was a poor generator of H(2)O(2) in tissue culture medium, had no effect on the intracellular glutathione level, its cytotoxicity was unaffected by catalase, and it did not induce lipid peroxidation. However, (-)-Catechin gallate(CG) did enhance Fe(2+)-induced, lipid peroxidation. (-)-Catechin gallate(CG)-induced apoptosis was detected by nuclear staining, both with acridine orange and by the more specific TUNEL procedure. The lack of caspase-3 activity in cells exposed to (-)-Catechin gallate(CG) and the detection of a DNA smear, rather than of discrete internucleosomal DNA fragmentation, upon agarose gel electrophoresis, suggest, possibly, that the mode of cell death was by a caspase-independent apoptotic pathway.
CONCLUSIONS:
The overall cytotoxicity of (-)-Catechin gallate(CG) was similar to its epimer, ECG and both exhibited antiproliferative effects equivalent to, or stronger than, EGCG, the most abundant catechin in green tea.

In vitro inhibition of α-glucosidases and glycogen phosphorylase by catechin gallates in green tea.[Reference: WebLink]

Food Chem.,2010,122(4):1061-6.

We investigated in vitro inhibition of mammalian carbohydrate-degrading enzymes by green tea extract and the component catechins, and further evaluated their inhibitory activities in cell cultures.
METHODS AND RESULTS:
The extract showed good inhibition toward rat intestinal maltase and rabbit glycogen phosphorylase (GP) b, with IC50 values of 45 and 7.4 μg/ml, respectively. The polyphenol components, catechin 3-gallate (CG), gallocatechin 3-gallate (GCG), epicatechin 3-gallate (ECG), and epigallocatechin 3-gallate (EGCG), were good inhibitors of maltase, with IC50 values of 62, 67, 40, and 16 μM, respectively, and EGCG also showed good inhibition toward maltase expressed on Caco-2 cells, with an IC50 value of 27 μM. The ungallated catechins, such as catechin, gallocatechin (GC), epicatechin (EC), and epigallocatechin (EGC), showed no significant inhibition toward GP b, whereas the gallated catechins CG, GCG, ECG, and EGCG inhibited the enzyme, with IC50 values of 35, 6.3, 27, and 34 μM. From multiple inhibition studies by Dixon plots, GCG appears to bind a new allostelic site, the indole inhibitor site. These gallated catechins also inhibited glucagon-stimulated glucose production dose-dependently, with IC50 values ranging from 33 to 55 μM.
CONCLUSIONS:
Dietary supplementation with these gallated catechins or the green tea extract containing them, which inhibits both α-glucosidases and GP in vitro and in cell culture, would contribute to the protection or improvement of type 2 diabetes.

Protocol of (-)-Catechin gallate(CG)

Cell Research

Epicatechin gallate and catechin gallate are superior to epigallocatechin gallate in growth suppression and anti-inflammatory activities in pancreatic tumor cells.[Pubmed: 21241417 ]

Cancer Sci. 2011 Apr;102(4):728-34.

Green tea catechins are considered as possible cancer preventive agents for several cancer types but little is known regarding their effects on pancreatic cancer cells. The best studied catechin and the major polyphenol present in green tea is epigallocatechin gallate (EGCG).
METHODS AND RESULTS:
In the present study, we investigated the in vitro anti-tumoral properties of EGCG on human pancreatic ductal adenocarcinoma (PDAC) cells PancTu-I, Panc1, Panc89 and BxPC3 in comparison with the effects of two minor components of green tea catechins, catechin gallate (CG) and epicatechin gallate (ECG). We found that all three catechins inhibited proliferation of PDAC cells in a dose- and time-dependent manner. Interestingly, CG and ECG exerted much stronger anti-proliferative effects than EGCG. Western blot analyses performed with PancTu-I cells revealed catechin-mediated modulation of cell cycle regulatory proteins (cyclins, cyclin-dependent kinases [CDK], CDK inhibitors). Again, these effects were clearly more pronounced in CG or ECG than in EGCG-treated cells. Importantly, catechins, in particular ECG, inhibited TNFα-induced activation of NF-κB and consequently secretion of pro-inflammatory and invasion promoting proteins like IL-8 and uPA.
CONCLUSIONS:
Overall, our data show that green tea catechins ECG and CG exhibit potent and much stronger anti-proliferative and anti-inflammatory activities on PDAC cells than the most studied catechin EGCG.

Preparing Stock Solutions of (-)-Catechin gallate(CG)

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.2606 mL	11.3028 mL	22.6055 mL	45.211 mL	56.5138 mL
5 mM	0.4521 mL	2.2606 mL	4.5211 mL	9.0422 mL	11.3028 mL
10 mM	0.2261 mL	1.1303 mL	2.2606 mL	4.5211 mL	5.6514 mL
50 mM	0.0452 mL	0.2261 mL	0.4521 mL	0.9042 mL	1.1303 mL
100 mM	0.0226 mL	0.113 mL	0.2261 mL	0.4521 mL	0.5651 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.

References on (-)-Catechin gallate(CG)

Synthesis and preliminary anticancer activity studies of C4 and C8-modified derivatives of catechin gallate (CG) and epicatechin gallate (ECG).[Pubmed:17168588]

J Org Chem. 2006 Dec 22;71(26):9701-12.

We have developed an improved and reliable method for stereoselective functionalization at C4 of naturally occurring (+)-catechin. Our method utilizes DDQ oxidation followed by trapping of the quinonemethide intermediate with allyl alcohol. The quinonemethide intermediate can be regenerated from the allyl ether by exposure to boron trifluoride diethyl etherate. This reactive intermediate can be trapped with a wide range of external nucleophiles. NBS bromination, lithium halogen exchange, and alkylation gave access to C8-allyl derivatives of (+)-catechin, and this allyl group was used in a series of cross-metathesis experiments to prepare novel dimeric catechin-derived products. Gallate ester derivatives of the novel C4- and C8-substituted catechins were prepared, and these materials were screened for potential anticancer activity in a range of human cancer cell lines. From these preliminary cytotoxicity assays (MTT) we found that C8-propyl-catechin gallate was more active (IC50 = 31 microM) than catechin gallate (CG, IC50 = 53 microM) or epicatechin gallate (ECG, IC50 = 76 microM) against the colorectal adenocarcinoma cell line HCT116. Differential sensitivity in pancreas (Pan1), bladder (RT112), stomach (MGLVA1), liver (HepG2), and fibroblasts (46Br.1G1) cell lines was also observed.

In vitro cytotoxicity of (-)-catechin gallate, a minor polyphenol in green tea.[Pubmed:17606338]

Toxicol Lett. 2007 Jul 10;171(3):171-80.

The cytotoxicity of (-)-catechin gallate (CG), a minor polyphenolic constituent in green tea, towards cells derived from tissues of the human oral cavity was studied. The sequence of sensitivity to CG was: immortalized epithelioid gingival S-G cells>tongue squamous carcinoma CAL27 cells>salivary gland squamous carcinoma HSG cells>>normal gingival HGF-1 fibroblasts. Further studies focused on S-G cells, the cells most sensitive to CG. The response of the S-G cells to CG was dependent on the length of exposure, with midpoint cytotoxicity values of 127, 67 and 58muM CG for 1-, 2- and 3-day exposures, respectively. The sequence of sensitivity of the S-G cells to various green tea catechins was characterized as follows: CG, epicatechin gallate (ECG)>epigallocatechin gallate (EGCG)>epigallocatechin (EGC)>>epicatechin (EC), catechin (C). The cytotoxicity of CG, apparently, was not due to oxidative stress as it was a poor generator of H(2)O(2) in tissue culture medium, had no effect on the intracellular glutathione level, its cytotoxicity was unaffected by catalase, and it did not induce lipid peroxidation. However, CG did enhance Fe(2+)-induced, lipid peroxidation. CG-induced apoptosis was detected by nuclear staining, both with acridine orange and by the more specific TUNEL procedure. The lack of caspase-3 activity in cells exposed to CG and the detection of a DNA smear, rather than of discrete internucleosomal DNA fragmentation, upon agarose gel electrophoresis, suggest, possibly, that the mode of cell death was by a caspase-independent apoptotic pathway. The overall cytotoxicity of CG was similar to its epimer, ECG and both exhibited antiproliferative effects equivalent to, or stronger than, EGCG, the most abundant catechin in green tea.

Epicatechin gallate and catechin gallate are superior to epigallocatechin gallate in growth suppression and anti-inflammatory activities in pancreatic tumor cells.[Pubmed:21241417]

Cancer Sci. 2011 Apr;102(4):728-34.

Green tea catechins are considered as possible cancer preventive agents for several cancer types but little is known regarding their effects on pancreatic cancer cells. The best studied catechin and the major polyphenol present in green tea is epigallocatechin gallate (EGCG). In the present study, we investigated the in vitro anti-tumoral properties of EGCG on human pancreatic ductal adenocarcinoma (PDAC) cells PancTu-I, Panc1, Panc89 and BxPC3 in comparison with the effects of two minor components of green tea catechins, catechin gallate (CG) and epicatechin gallate (ECG). We found that all three catechins inhibited proliferation of PDAC cells in a dose- and time-dependent manner. Interestingly, CG and ECG exerted much stronger anti-proliferative effects than EGCG. Western blot analyses performed with PancTu-I cells revealed catechin-mediated modulation of cell cycle regulatory proteins (cyclins, cyclin-dependent kinases [CDK], CDK inhibitors). Again, these effects were clearly more pronounced in CG or ECG than in EGCG-treated cells. Importantly, catechins, in particular ECG, inhibited TNFalpha-induced activation of NF-kappaB and consequently secretion of pro-inflammatory and invasion promoting proteins like IL-8 and uPA. Overall, our data show that green tea catechins ECG and CG exhibit potent and much stronger anti-proliferative and anti-inflammatory activities on PDAC cells than the most studied catechin EGCG.

Description

(-)-Catechin gallate is a minor constituent in green tea catechins. (-)-Catechin gallate inhibits the activity of COX-1 and COX-2 enzymes.

Keywords:

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