l-epicatechingallate
(-)-epicatechin gallate
CAS: 1257-08-5
Molecular Formula: C22H18O10
l-epicatechingallate - Names and Identifiers
| Name | (-)-epicatechin gallate |
| Synonyms | ECG epicatechol,gallate l-epicatechingallate (-)-epicatechin gallate EPICATECHIN GALLATE, (-)-(P) 8-methoxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-2(1h)-one 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate (2R,3S)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-chromen-5-yl 3,4,5-trihydroxybenzoate |
| CAS | 1257-08-5 |
| EINECS | 603-088-4 |
| InChI | InChI=1/C22H18O10/c23-11-6-18-12(8-17(28)21(31-18)9-1-2-13(24)14(25)3-9)19(7-11)32-22(30)10-4-15(26)20(29)16(27)5-10/h1-7,17,21,23-29H,8H2/t17-,21+/m0/s1 |
| InChIKey | LSHVYAFMTMFKBA-TZIWHRDSSA-N |
l-epicatechingallate - Physico-chemical Properties
| Molecular Formula | C22H18O10 |
| Molar Mass | 442.37 |
| Density | 1.80±0.1 g/cm3(Predicted) |
| Melting Point | 257-258°C |
| Boling Point | 861.7±65.0 °C(Predicted) |
| Specific Rotation(α) | -182～-194°(D/20℃)(c=0.2,CH3OH) |
| Flash Point | 325.2°C |
| Water Solubility | Soluble in water, acetone, DMSO, methanol. |
| Solubility | Soluble in water. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White powder |
| Color | White to Off-White |
| pKa | 7.75±0.25(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Light Sensitive |
| Sensitive | Sensitive to heat |
| Refractive Index | 1.769 |
| MDL | MFCD00075936 |
| Physical and Chemical Properties | Derived from this product is green tea isolate. |
l-epicatechingallate - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | DH9030000 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 29329990 |
l-epicatechingallate - Reference Information
| Plant source: | Tea |
| Tea polyphenol active ingredient | Epicatechin gallate is abbreviated as EGCG, which is an ester formed by gallate catechol and gallic acid. It is a kind of tea polyphenol. It is a flavonoid, right-type ester catechin. epicatechin gallate is a catechin monomer isolated from tea and is the main component of the biological activity of tea polyphenols. |
| tea polyphenols | tea polyphenols are the general term for polyphenols in tea, and are a kind of polyphenols with catechins as the main body with biological oxidation. Chinese tea usually contains 20% ~ 30% tea polyphenols. Tea polyphenols can be divided into 5 categories, of which flavanols (mainly catechins) are the most important, in addition to anthocyanins, flavanones, flavonols and phenolic acids. Catechins account for about 50% ~ 70% of the total tea polyphenols and 12% ~ 24% of the dry weight of tea. It is a class of compounds with relatively complex structures, including 4 simple catechins (also called non-ester catechins) and 2 complex catechins (also called ester catechins). The content of tea polyphenols in tea is roughly more green tea than black tea, and more summer and autumn tea than spring tea. The main pharmacodynamic effects of tea polyphenols are: (1) reduce blood lipids and inhibit atherosclerosis. (2) Strengthen capillaries and lower blood sugar. (3) radiation resistance. (4) Anti-aging. (5) Anti-cancer and anti-mutation. (6) Sterilization. fig. 2 shows the main chemical substances contained in tea polyphenols |
| biological activity | biological activity is poor when taken orally, and the curative effect of taking 800mg dose is one order of magnitude lower than the actual situation. |
| Toxicity | EGCG may cause cancer. Studies have found that the intake of polyphenols during pregnancy will increase the risk of neonatal leukemia, and pregnant women are not easy to consume biological flavonoids. Eating tea or coffee during pregnancy may increase the risk of malignant central nervous system (CNS) tumors in children, but the specific mechanism is unknown. |
| biosynthesis of epicatechin gallate | fig. 3 shows the synthesis pathway of epicatechin gallate in plants. the enzymes involved in the above synthetic pathway mainly include phenylalanine deaminase (phenylalanine ammonialyase, PAL), cinnamic acid carboxylase (cinnamate 4 hydroxylase,C4H), 4 coumaryl CoA ligase (4 coumaroyl CoA ligase, 4CL), chalcone isomerase (chalcone isomerase,CHI), chalcone synthase (chalcone synthase,CHS), flavanone 3 'hydroxylase (flavonoid3' hydroxylase, f3'H), flavanone 3 ',5' hydroxylase (flavonoid3 ',5' hydroxylase,F3'5'H), dihydroflavone 3 hydroxylase ((2S) flavanone 3 hydroxylase,F3H), dihydroflavanol 4 reductase (dihydroflavonol 4 reductase,DFR), colorless anthocyanin reductase (leucoanthocyanidin reductase,LAR), anthocyanin reductase (anthocyanidin reductase,ANR), anthocyanin synthetase (anthocyanidin synthase,ANS), flavonoid glycosyltransferase UDPG flavonoid glucosyl transferase UFGT, etc. |
| antibacterial effect | epicatechin gallate has antibacterial effect on common Proteus, Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus mutans, botulinum Many pathogenic bacteria such as Bacillus, Lactobacillus, Vibrio cholerae, especially intestinal pathogenic bacteria have different degrees of inhibition and killing effects. At the same time, epicatechin gallate can effectively prevent antibiotic-resistant staphylococcal infection, and also has inhibitory activity on hemolysin ECG and EGCG. In addition, it also has a strong inhibitory effect on pathogenic fungi that can cause human skin diseases, such as head white tinea, spotted blister white tinea, sweaty blister white tinea and stubborn tinea. |
| antioxidant effect | epatechin gallate is a polyphenol hydroxyl chemical substance, which is easily oxidized into esters and provides proton h, so it has remarkable antioxidant characteristics. The antioxidant capacity of tea polyphenols is 18 times that of vitamin E and 3-10 times that of vitamin C. It has the function of blocking the synthesis of N-nitroso compounds, inhibiting the activity of lipoxygenase and lipid peroxidation. It shows superior disease prevention and treatment effects in many aspects such as anti-cancer, anti-cancer, anti-mutation, anti-aging, prevention and treatment of cardiovascular diseases, and treatment of hepatitis. |
| other pharmacological effects | 1. hypoglycemic effect. several experimental data confirm that tea polyphenols are inhibitors of sucrase, so it can inhibit the conversion of sucrose to glucose and reduce blood sugar. 2. Antiviral effect, has the effect of inhibiting influenza A and B viruses, and has an inhibitory effect on human respiratory system synospora virus (RSV). In addition, tea polyphenols have a strong anti-inhibitory effect on gastroenteritis virus, hepatitis A virus, and plant virus. In recent years, it has been proved that tea polyphenol is indeed a new strong inhibitor of HIV-IRT. 3. Anti-cancer and anti-mutation effects, epatechin gallate can not only inhibit mutations induced by various chemical carcinogens, but also inhibit some mixed carcinogens (tobacco mist concentrate, coal tar, smoked fish extract, X-ray) Mutagenic effect. 4. For cardiovascular diseases, studies have proved that tea polyphenols have the effects of anticoagulation, fibrinolysis, anti-platelet aggregation, lowering blood pressure, lowering blood lipids, preventing and treating atherosclerosis, and protecting myocardium. 5. Anti-allergic and anti-inflammatory effects. Tea polyphenols have significant inhibitory effects on hyaluronic acid, among which theaflavins have 99.1% inhibitory activities to kill gallic acid, which can effectively inhibit rapid allergic reactions. 6. The gastrointestinal protective function can inhibit the H-K-ATP enzymes on the gastric mucosa, thereby fundamentally inhibiting the secretion of gastric acid, reducing the stimulation and damage of gastric acid to the gastric mucosa, and at the same time can treat ulcers. It also has a certain relief effect on gastrointestinal spasm. |
| store | sealed and placed in a cool and dry environment to avoid humidity, strong light and high temperature. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: epigallocatechin gallate is the most effective active ingredient in tea polyphenols. It has antibacterial, antiviral, antioxidant, anti-arteriosclerosis, anti-thrombosis, anti-vascular proliferation and anti-inflammatory effects. EGCG has a good anti-tumor effect: especially gastric cancer, leukemia, liver cancer, lung cancer has a certain preventive and therapeutic effect. Especially for cardiovascular diseases, it can protect the endothelium, and has very clear basic effects such as promoting vasodilation, preventing infectious diseases, preventing oxidative damage, preventing inflammation, and preventing platelet coagulation. As an antioxidant for adjuvant treatment of some methicillin-resistant bacteria. (-)Epicatechin gallate is a polyphenol apoptosis inducer in tumor cells commonly found in green tea. Studies suggest that (-)Epicatechin gallate causes anti-proliferative and anti-inflammatory effects on pancreatic ductal adenocarcinoma cells. Alternate studies show that (-)Epicatechin gallate can suppress H2O2-induced genotoxicity in vitro in C6 astroglial cells. In contrast at high concentrations polyphenols are shown to reverse the genoprotective effects that they produce at low concentrations. Furthermore, (-)Epicatechin gallate can inhibit the development of mouse blastocysts via apoptosis. Studies indicate that (-)Epicatechin gallate binds to the cell membrane in methicillin-resistant Staphylococcus aureus which decreases the fluidity of the bilayer and induces changes in gene expression. Also upon binding to penicillin-binding protein (PBP) 2a on the cell membrane of Staphylococcus aureus the membrane is sensitized to Oxacillin and other &beta-lactam agents. |
Last Update：2024-04-09 20:45:29
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