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(-)-Epicatechin gallate

Active ingredients of the Tea Polyphenol Tea polyphenols Biological activity Toxicity Biosynthesis pathway of Epicatechin gallate Antibacterial effect Anti-oxidization effect Other pharmacological effects Storage
(-)-Epicatechin gallate
(-)-Epicatechin gallate
CAS No.
1257-08-5
Chemical Name:
(-)-Epicatechin gallate
Synonyms
L-ECG;(-)-ECG;Teatannin;Nsc636594;Aids000675;Aids-000675;ECG)()-Epicatechin;EPICATECHIN GALLATE;epicatechol,gallate;3-O-Galloylgatechin
CBNumber:
CB0738543
Molecular Formula:
C22H18O10
Formula Weight:
442.37
MOL File:
1257-08-5.mol

(-)-Epicatechin gallate Properties

Melting point:
257-258°C
storage temp. 
2-8°C
Water Solubility 
Soluble in water, acetone, DMSO, methanol.
InChIKey
LSHVYAFMTMFKBA-TZIWHRDSSA-N
CAS DataBase Reference
1257-08-5(CAS DataBase Reference)

SAFETY

Safety Statements  24/25
WGK Germany  3
RTECS  DH9030000
10-23

(-)-Epicatechin gallate price More Price(10)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich E3893 (?)-Epicatechin gallate ≥98% (HPLC), from green tea 1257-08-5 10mg $187 2018-11-13 Buy
Sigma-Aldrich 03950590 Epicatechin gallate primary reference standard 1257-08-5 10mg $417 2018-11-13 Buy
TCI Chemical E0890 (-)-Epicatechin Gallate >98.0%(HPLC) 1257-08-5 20mg $202 2018-11-22 Buy
TCI Chemical E0890 (-)-Epicatechin Gallate >98.0%(HPLC) 1257-08-5 100mg $704 2018-11-22 Buy
Alfa Aesar J60814 (-)-Epicatechin gallate 1257-08-5 10mg $151 2018-11-13 Buy

(-)-Epicatechin gallate Chemical Properties,Uses,Production

Active ingredients of the Tea Polyphenol

Epicatechin gallate briefly referred to as EGCG, being the ester formed by epigallocatechin and gallate acid, belonging to a kind of tea polyphenols; is a kind of flavonoids, D-form ester catechins.
Epicatechin gallate is the cathchin monomer isolated from the tea, being the major active ingredients of polyphenols.

Figure 1 shows the stereochemical structure of epicatechin gallate

Tea polyphenols

Tea polyphenols are the general term of the tea polyphenols, being a kind of polyphenols using catechins as the major body with biological oxidation effect. Chinese tea usually contains 20% to 30% tea polyphenols. Tea polyphenols can be divided into five categories, of which the flavanol (mainly catechins) is the most important; besides there are also anthocyanins, flavonoids, flavonols and phenolic acids. Catechins account for about 50% to 70% of the total amount of tea polyphenols, accounting for 12% to 24% of the dry weight of tea. It is a compound of complex structure, including four kinds of simple catechins (also called non-esters type catechins) and two kinds of complex catechins (also known as ester type catechins). The trend of the content of tea polyphenols is generally as below: green tea is higher than black tea; summer and autumn tea are more than spring tea. The main pharmacological effects of tea polyphenols are:
(1) Lower the blood lipid, inhibit atherosclerosis. (2) Enhance the capillaries, lower blood sugar. (3) Anti-radiation. (4) Anti-aging. (5) Anti-cancer and anti-mutation. (6) Bactericidal effect.

Figure 2 is the tea polyphenols containing the major chemical substances;

Biological activity

Oral biological activity is poor; the efficacy of taking a dosage of 800 mg is actually an order of magnitude lower than the real situation.

Toxicity

EGCG might be carcinogenic; study has found that during pregnancy, intake of polyphenols will increase the risk of neonatal leukemia; it is not good for pregnant women to uptake bioflavones; during pregnancy, administration of tea or coffee during pregnancy may increase the risk for children of suffering from malignant tumor of central nervous system (CNS), and the specific mechanism remains unknown.

Biosynthesis pathway of Epicatechin gallate


Figure 3 shows the synthesis of Epicatechin gallate in plants.
Enzymes involved in the synthesis pathway include phenylalanine ammonialyase (PAL), cinnamate 4-hydroxylase (C4H), 4-¬coumaroyl¬CoA ligase (4CL), chalcone isomerase (CHI), chalcone synthase (CHS), flavonoid3’¬hydroxylase (F3’H),flavonoid3’, 5’¬hydroxylase (F3’5’H), (2S)¬flavanone 3¬hydroxylase (F3H), dihydroflavonol-4-¬reductase (DFR), leucoanthocyanidin reductase (LAR), anthocyanidin reductase,ANR、anthocyanidin synthase (ANS) and UDPG¬ flavonoid glucosyl transferase UFGT and so on.

Antibacterial effect

Epicatechin gallate has antibacterial effect, having varied bacteriostatic and bactericidal effect against many kinds of common pathogens including Proteus, Staphylococcus aureus, Staphylococcus epidermidis; Streptococcus, Botox, Lactobacillus and Vibrio cholera, especially intestinal pathogens. Moreover, epicatechin gallate can also effectively prevent the infection of antibiotic-resistant staphylococcus; it has inhibitory effect against hemolysin ECG and EGCG. In addition, it also has inhibitory effect against pathogenic fungi that can cause human skin disease, such as the head tinea alba, plaque blister white ringworm, sweat bubble white ringworm and stubborn tinea and other parasitic fungi.

Anti-oxidization effect

Epicatechin gallate belongs to a polyphenol hydroxyl chemical, and is quite easily to be oxidized into esters and provide proton H, thus having significant antioxidant property. The antioxidant capacity of tea polyphenols is 18 times than that of vitamin E; 3 to 10 times than that of vitamin C. It has the ability to block the synthesis of N-nitroso compounds, inhibit the activity of lipoxygenase and lipid peroxidation. This makes it play excellent disease prevention and treatment effect in the anti-cancer, anti-mutation, anti-aging, prevention and treatment of cardiovascular disease, treatment of hepatitis and many other aspects.

Other pharmacological effects

  • Hypoglycemic effect, a number of experimental data have confirmed that tea polyphenols is an invertase inhibitor, so it can inhibit the conversion of sucrose to glucose, leading to the decrease of the blood sugar.
  • Antiviral effect, it has inhibitory effect against influenza A, influenza B virus as well as the human respiratory system covariate virus (RSV). In addition, tea polyphenols also have a strong anti-inhibitoryeffect against gastroenteritis virus, hepatitis A virus and plant viruses. In recent years, it has been confirmed that tea polyphenol is a strong novel inhibitor of HIV-IRT.
  • Anti-cancer, anti-mutation effect; epicatechin gallate not only inhibits a variety of chemical carcinogen-induced mutations, but also inhibit the mutagenic effect of some kinds of mixed carcinogens (tobacco fog thickener, coal tar, smoked fish extract, X Ray).
  • For the treatment of cardiovascular disease; studies have shown that tea polyphenols have various effects including anticoagulant, promote fibrinolysis, anti-platelet aggregation, lowering blood pressure, lowering blood pressure, prevention and treatment of atherosclerosis as well as protecting the myocardium.
  • Anti-allergic and anti-inflammatory effect, tea polyphenols has a significant inhibitory effect on the transparent enzyme, among which theaflavin gallate has an inhibitory activity of 99.1%, being able to effectively inhibit the rapid allergic reaction.
  • Gastrointestinal protection function. It can inhibit the H-K-ATPase in the gastric mucosa, which fundamentally inhibits the secretion of gastric acid. This reduces the gastric irritation and injury by gastric acid. It can treat ulcers and alleviate the gastrointestinal spasm as well.

Storage

It should be sealed, placed in a cool dry environment, to be avoided of moisture, light and high temperature.

Chemical Properties

White powder

Uses

One of the catechin isomers and a potent antioxidant that can modulate a wide range of membrane proteins. Its bilayer-modifying potency was tested using gramicidin A (gA) channels as probes. All the c atechins alter gA channel function and modify bilayer properties, with a 500-fold range in potency. The gallate group causes current block, as evident by brief downward current transitions.

Uses

An antioxidant investigated as an adjunct treatment of some methyicillin resistant bacteria.

Definition

ChEBI: A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.

Uses

The catechins, including (?)-epicatechin (EC) and (?)-epigallocatechin gallate (EGCG) , are polyphenols which are abundant in green and black teas. (?)-Epicatechin gallate (ECG) is a natural catechin with a single galloyl group. Like EGCG, it inhibits the growth of cancer cells and has anti-inflammatory effects. The hydroxyl groups of ECG contribute to its potent antioxidant activity and facilitate the killing of methicillin-resistant strains of S. aureus.

(-)-Epicatechin gallate Preparation Products And Raw materials

Raw materials

Preparation Products


(-)-Epicatechin gallate Suppliers

Global( 202)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Nanjing Dolon Biotechnology Co.,Ltd.
18905173768
sales@dolonchem.com CHINA 2982 58
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32764 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 14297 60
Chengdu Biopurify Phytochemicals Ltd.
18080483897
maggie@biopurify.com CHINA 2200 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 20001 58
Kono Chem Co., Ltd
+86-132 8924 6953
info@konochemical.com CHINA 2164 58
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3624 58
Shanghai BeiZhuo Biotech Co., Ltd. 021-61119791/13386096464
021-50190009 bzswkf@foxmail.com China 3983 50
Nanjing Duolong Bio-tech Co.,Ltd. 18905173768
025-83263139 52513593@qq.com China 4107 50
Shanghai Macklin Biochemical Co.,Ltd. 15221275939
021-51821727 shenlinxing@macklin.cn China 15835 55

View Lastest Price from (-)-Epicatechin gallate manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-15 (-)-Epicatechin gallate
1257-08-5
US $8.00 / kg 1kg 99% 100MT career henan chemical co

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