3D Mol Similar

(-)-Epicatechin gallate

: Iupac Name：[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,
4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate; CAS No.: 1257-08-5; Molecular Weight：442.37232; Modify Date.: 2022-11-09 22:18; Introduction: 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 catechins 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. View more+

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1. Names and Identifiers

: 1.1 Name; (-)-Epicatechin gallate; 1.2 Synonyms; (&minus)-Epicatechin gallate (&minus)-Epicatechin gallate,from green tea (-)-cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate (-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallate (-)-epicatechin-3-gallate (-)-Epicatechingallate (2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate 8-methoxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-2(1h)-one Benzoic acid, 3,4,5- trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-ylester, (2R-cis)-, Benzoic acid, 3,4,5-trihydroxy-, (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester ECG Epicatechin gallate EPICATECHIN GALLATE, (-)- SNAP-N-SHOOT 0.1mg/ml(P) EPICATECHIN GALLATE, (-)-(P) Epicatechol, 3-gallate, (-)- (8CI) epicatechol,gallate l-epicatechingallate MFCD00075936; View all

1.3 CAS No.: 1257-08-5

1.4 CID: 107905

1.5 EINECS(EC#): 603-088-4

1.6 Molecular Formula: C22H18O10 (isomer)

1.7 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

1.8 InChIkey: LSHVYAFMTMFKBA-TZIWHRDSSA-N

1.9 Canonical 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

1.10 Isomers Smiles: C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

2. Properties

2.1 Density: 1.685

2.1 Melting point: 257-258°C

2.1 Boiling point: 920.9°C at 760 mmHg

2.1 Refractive index: 1.769

2.1 Flash Point: 325.2°C

2.1 Precise Quality: 442.09000

2.1 PSA: 177.14000

2.1 logP: 2.52760

2.1 Appearance: White to Light yellow to Light orange powder to crystal

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

2.3 Chemical Properties: White powder

2.4 Color/Form: Powder

2.5 pKa: 7.75±0.25(Predicted)

2.6 Water Solubility: Soluble in water, acetone, DMSO, methanol.

2.7 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 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. (-)-Epicatechin gallateSupplier

3.2 Usage: 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 catechins 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.

4. Safety and Handling

4.1 Safety Statements: 24/25

4.1 RIDADR: NONH for all modes of transport

4.1 WGK Germany: 3

4.1 RTECS: DH9030000

4.1 Specification: (-)-Epicatechin gallate (CAS NO.1257-08-5) also can be called (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate) ; and (-)-ECG .

4.2 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	> 1gm/kg (1000mg/kg)		Japanese Kokai Tokyo Koho Patents. Vol. #93-944,

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

1257-08-5Total: 22 Synthesis Route

100-53-8 104 Suppliers

37064-35-0

80418-27-5

1257-08-5 161 Suppliers

154-23-4 137 Suppliers

Literatures:
Chemical and Pharmaceutical Bulletin, , vol. 29, # 10 p. 2862 - 2870
Yield: null

1486-47-1

1257-08-5 161 Suppliers

Literatures:
Bioorganic and Medicinal Chemistry, , vol. 12, # 13 p. 3521 - 3527
Yield: null

1486-48-2 17 Suppliers

1257-08-5 161 Suppliers

Literatures:
Bioorganic and Medicinal Chemistry, , vol. 12, # 13 p. 3521 - 3527
Yield: null

View all

7. Precursor and Product

precursor:

126715-92-2

87292-54-4

126715-82-0

63604-98-8

1255211-38-1

918157-97-8

100-53-8

82916-01-6

256236-30-3

1309248-11-0

1309248-12-1

87292-49-7

732298-11-2

1486-47-1

1255211-63-2

1309248-14-3

732298-08-7

1309248-10-9

20728-73-8

1486-48-2

918158-03-9

20728-98-7

View all

product :

6500-64-7

191666-22-5

30462-35-2

111397-00-3

130405-40-2

149-91-7

1707-75-1

108907-44-4

31129-95-0

30462-34-1

28543-07-9

621-54-5

490-46-0

31129-94-9

View all

8. Other Information

8.0 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

8.1 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;; View all

8.2 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.

8.3 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.

8.4 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.

8.5 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.

8.6 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.

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

8.8 Chemical Properties: White powder

8.9 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.

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

8.11 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.

8.12 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.

8.13 Usage: (-)-Epicatechin gallate is used as an antioxidant investigated as an adjunct treatment of some methyicillin resistant bacteria. 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. 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 catechins alter gA channel function and modify bilayer properties, with a 500-fold range in potency.

8.14 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.

8.15 Uses: (-)-Epicatechin gallate is polyphenols which are abundant in green and black teas. (-)-Epicatechin gallate (ECG) is a natural catechin with a single galloyl group. The hydroxyl groups of ECG contribute to its potent antioxidant activity and facilitate the killing of methicillin-resistant strains of S. aureus.

8.16 General Description: (?)-Epicatechin gallate is one of the major polyphenols present in green tea. It belongs to the catechin gallates group of organic compounds. ECG has a chemical structure like that of (?)-epigallocatechin gallate (EGCG), the other major polyphenol found in green tea.

9. Computational chemical data

Molecular Weight: 442.37232g/mol
Molecular Formula: C₂₂H₁₈O₁₀
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 442.08999677
Monoisotopic Mass: 442.08999677
Complexity: 649
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 7
Hydrogen Bond Acceptor Count: 10
Topological Polar Surface Area: 177
Heavy Atom Count: 32
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4PAAAAAAAAAAAAAAAAAAAAAAAAAA0YMEAAAAAAACRUAAAGgAACAAADBSgmAIwDoAABgCIAiDSCAACCAAkIAAIiAEGiMgNJzKGNRqCeSGlwBULuYfK7PzOIAABCAAIQABAAAIQABCAAAAAAAAAAA==

10. Question & Answer

Application and synthesis of (-)-Epicatechin gallate Jul 22 2023
Introduction (-)-Epicatechin gallate (Epicatechin gallate, ECG), (-)-Epicatechin gallate appears as white powder and is easily soluble in organic solvents such as water and ethanol. (-)-Epicatechin ga..
Can Epicatechin Gallate be a Novel Inhibitor for NDM-1 and a Potential Cancer Treatment? Oct 10 2022
Introduction Tea, a popular beverage consumed by two-thirds of the world's population, can be categorized into three types: green tea, black tea, and oolong tea. Research has shown that green tea extr..

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