Name | (-)-epigallocatechin gallate |
Synonyms | EGCG Green Tea TEA CATECHIN Green Tea P.E Tea polyphenol Tea Polyphenols Green Tea Extract Green tee extract Green Tea Extract Powder L-Epigallocatechin Gallate (-)-epigallocatechin gallate Green tea extract Polyphenols Epigallocatechin-3-Monogallate (-)-Epigallocatechin Gallate-d6 (-)-Epigallocatechin-3-O-gallate (20 mg) (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate (-)-CIS-2-(3,4,5-TRIHYDROXYPHENYL)-3,4-DIHYDRO-1(2H)-BENZOPYRAN-3 ,5,7-TRIOL 3-GALLATE(-)-CIS-3,3',4',5,5',7-HEXAHYDROXY-FLAVANE-3-GALLATE |
CAS | 989-51-5 84650-60-2 |
EINECS | 479-560-7 |
InChI | InChI=1/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 |
InChIKey | WMBWREPUVVBILR-WIYYLYMNSA-N |
Molecular Formula | C22H18O11 |
Molar Mass | 458.37 |
Density | 1.90±0.1 g/cm3(Predicted) |
Melting Point | 222-224°C |
Boling Point | 909.1±65.0 °C(Predicted) |
Specific Rotation(α) | D -185 ±2°(ethanol) |
Flash Point | 320°C |
Water Solubility | Soluble in ethanol, dimethyl formamide, water. |
Solubility | Soluble in water. |
Vapor Presure | 3.71E-35mmHg at 25°C |
Appearance | White to pale pink powder |
Color | White to Light Brown |
Merck | 14,3526 |
pKa | 7.75±0.25(Predicted) |
Storage Condition | 2-8°C |
Stability | Stable, but may be light sensitive. Incompatible with strong oxidizing agents. |
Refractive Index | -175.5 ° (C=1, EtOH) |
MDL | MFCD00075940 |
Physical and Chemical Properties | White crystal, soluble in methanol, ethanol, DMSO and other organic solvents, derived from tea Tea. |
Use | The food industry is used for anti-oxidation, fresh-keeping and deodorizing, the pharmaceutical industry is used for antibacterial, anti-cancer and anti-aging, and the daily chemical products are used as special functional additives. |
In vitro study | (-)-Epigallocatechin gallate has potent antioxidant effects in healthy cells and reduces oxidative damage, acts as an anti-angiogenic and anti-tumor agent, and is also a modulator of tumor cell response to chemotherapy. (-)-Epigallocatechin gallate has a variety of anti-tumor effects, such as anti-proliferation, anti-angiogenesis, blocking various cancer cell transformation, cell cycle arrest and inhibition of tumor metastasis. (-)-Epigallocatechin gallate by regulating multiple tumor-associated cell signaling pathways (regulating the expression levels of key signaling proteins, such as nuclear factor-κB, MAPKs, and activator protein -1,EGFR,IGF,COX-2) affect the methylation of tumor genes and the binding of ligands to membrane receptors to exert anti-tumor effects. (-)-Epigallocatechin gallate has an immunomodulatory effect. Many types of immune cells are affected to varying degrees by (-)-Epigallocatechin gallate in both the innate and adaptive immune systems. Among these effects, significant effects on T cells have been repeatedly demonstrated, including T cell activation, proliferation, differentiation, and cytokine production. Studies based on animal models of autoimmune disease reported that green tea/EGCG treatment improved the animal's condition. (-)-Epigallocatechin gallate has anti-infective activity. The antiviral activity of (-)-Epigallocatechin gallate, produced by different modes of activation, has been demonstrated in many species of viruses, such as retroviruses, Orthomyxoviridae and Flaviviridae, also included are important human pathogenic bacteria such as the human immunodeficiency virus, influenza A virus, and hepatitis C virus. |
Safety Description | 24/25 - Avoid contact with skin and eyes. |
WGK Germany | 2 |
RTECS | KB5200000 |
FLUKA BRAND F CODES | 10-23 |
HS Code | 29339900 |
Toxicity | LD50 oral in mouse: 2170mg/kg |
an aqueous solution of light yellow to brown tea with tea aroma, dehydrated as a gray-white powdery solid or crystal, with astringent taste. Slightly moisture absorption, soluble in water, ethanol, ethyl acetate and other polar solvents, slightly soluble in oil and other weak polar solvents. It is weakly acidic, and the pH value of the aqueous solution is about 3 to 4. Heat and acid resistance is good, stable in the range of pH2 ~ 7, light and alkali resistance is poor, in the pH>8 or light easy oxidation polymerization. It has no inhibitory effect on fungi, yeast, lactic acid bacteria and acetic acid bacteria, but can effectively inhibit the oral variation causing dental caries
Streptococcus. In addition, tea polyphenols have antioxidant, anti-cancer, scavenging free radicals, lowering blood pressure and cholesterol and other biological functions.
The extraction methods of tea polyphenols from tea mainly include precipitation separation method, adsorption separation method, organic solvent extraction method, low temperature purification enzyme extraction method, salting-out method, the new developed methods include supercritical solvent extraction. Here we introduce the most commonly used calcium salt precipitation separation method. After crushing, the tea leaves are soaked in hot water at 80 ℃ for 30min in the extraction kettle, filtered, the filter cake is washed with a small amount of boiling water, the washing solution is combined with the filtrate, and other components such as caffeine can be extracted after the filter cake is dried. The filtrate is poured into the precipitation vessel, and saturated lime water, saturated lime water and saturated salt water are added at a ratio of about 1:6:5 of filtrate: lime water: salt water. After fully stirring, the mixture is allowed to stand for 30 min, filtration. The filter cake was then placed in an acidifier and 0. 5%~ 0.8% of the H2 S04, adjust the pH of a 7.1~7.2, and then use acetic acid or citric acid to adjust the pH value to 7.O, fully stirred, then stand for 30min, filter, wash, the filtrate was spray-dried to obtain the finished product.
can be used as food antioxidants and preservatives, widely used in animal and plant oils, aquatic products, beverages, candy, dairy products, fried food, spices, cosmetics and functional food antioxidant, but also to eliminate odor, preservation and other effects. If the object of use is lipid
Soluble, tea polyphenols can be dissolved in 95% food ethanol solution after adding. If the object is water-soluble, tea polyphenols can be directly added or dissolved in water after adding, the meat products can be directly with 0. 05% tea polyphenol solution impregnation or spraying.
Plant Source: | tea |
Introduction | (-)-epigallocatechin gallate is the most effective active ingredient in catechins, about 8%~ 13% of the gross weight of green tea, is the highest content of catechins in the composition. (-)-epigallocatechin gallate is an ester formed by α-linked phenol-based benzopyran and gallic acid, which has phenolic antioxidant properties, and has 6 ortho-phenolic hydroxyl groups in its molecular structure, there are therefore many properties that are superior to other catechins. |
function and use | (-)-epigallocatechin gallate has antibacterial anti-inflammatory, antioxidant and antimutagenic effects, can also be used as tumor multidrug resistance reversal agent, can improve the sensitivity of cancer cells to chemotherapy, reduce the toxicity to the heart, as well as the role of protecting the endothelium, can effectively promote vasodilation, reduce the occurrence of cardiovascular disease. |
consumption | ≤ 300 mg/day (based on EGCG) |
applicable food category | the scope of use does not include infant food. |
approval date | 2010-10-29 |
Announcement No. | Ministry of Health no.17, 2010 |
title | announcement on approval of new resource foods such as Haematococcus pluvialis |
Trait | off-white to light pink powder |
Epigallocatechin gallate | ≥ 94% (on dry basis) |
Caffeine | ≤0.1% |
Loss on drying | ≤5% |
biological activity | (-)-Epigallocatechin Gallate(EGCG) it is a potent antioxidant, Polyphenol flavonoid, isolated from green tea. Inhibits telomerase and DNA methyltransferase, blocks the activation of EGF receptors and HER-2 receptors, inhibits the activity of fatty acid synthase and glutamate dehydrogenase. |
Target | Value |
uses | has obvious anti-tumor effect, which can inhibit nuclear transcription factor kappa B(NF-κB), mitogen-activated protein kinase (MAPK), epidermal growth factor receptor, insulin-like growth factor, cyclooxygenase (COX)-2 and other related signaling pathways prevent tumor, tumor metastasis can also be prevented by inhibiting vascular endothelial growth factor, matrix metalloproteinase (MMP), urokinase plasminogen activator, etc. |