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(-)-epicatechin-3-O-gallate
3,4,5-trihydroxy-benzoic acid (2R,3R)-2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl ester

Supplier Sponsors

CAS Number: 1257-08-5Picture of molecule3D/inchi
FDA UNII: 92587OVD8Z
Nikkaji Web:J277.682K
XlogP3:1.50 (est)
Molecular Weight:442.37746000
Formula:C22 H18 O10
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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US Patents:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 861.70 °C. @ 760.00 mm Hg (est)
Flash Point: 581.00 °F. TCC ( 305.00 °C. ) (est)
logP (o/w): 2.670 (est)
Soluble in:
 water, 36.86 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Epicatechin gallate?ECG? 98%
BOC Sciences
For experimental / research use only.
(-)-epicatechin gallate >98%
Odor: characteristic
Use: (?)-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
Carbosynth
For experimental / research use only.
(-)-epiCatechin-3-o-gallate
ExtraSynthese
For experimental / research use only.
(-)-epiCatechin gallate (HPLC) ≥97.5%
Glentham Life Sciences
Epicatechin gallate
Santa Cruz Biotechnology
For experimental / research use only.
(-)-epiCatechin gallate ≥98%
Sigma-Aldrich
For experimental / research use only.
(-)-epiCatechin gallate ≥98% (HPLC), from green tea
TCI AMERICA
For experimental / research use only.
(-)-epiCatechin gallate >98.0%(HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50 > 1000 mg/kg
Japanese Kokai Tokyo Koho Patents. Vol. #93-944

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for (-)-epicatechin-3-O-gallate usage levels up to:
 not for fragrance use.
 
Recommendation for (-)-epicatechin-3-O-gallate flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :107905
National Institute of Allergy and Infectious Diseases:Data
[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Chemidplus:0001257085
RTECS:DH9030000 for cas# 1257-08-5
 
References:
 [(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):107905
Pubchem (sid):135064955
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB37944
FooDB:FDB017114
Export Tariff Code:2932.99.7000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 buckwheat tissue culture
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 carob bean
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 grape fruit
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 grape leaf
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 grape seed
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 rhubarb root
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 star fruit
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 tea green tea
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 tea leaf
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 tea shoot
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Synonyms:
 benzoic acid, 3,4,5-trihydroxy-, (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester
(-)-epicatechin gallate
(-)-epicatechin-3-gallate
(-)-epicatechingallate
epicatechol, 3-gallate, (-)- (8CI)
(2R,3R)-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-trihydroxy-benzoic acid (2R,3R)-2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl ester
 

Articles:

PubMed:Antifungal Properties of Crude Extracts, Fractions, and Purified Compounds from Bark of Curatella americana L. (Dilleniaceae) against Candida Species.
PubMed:Extract from Ceratonia siliqua Exhibits Depigmentation Properties.
PubMed:Separation of polyphenols and caffeine from the acetone extract of fermented tea leaves (Camellia sinensis) using high-performance countercurrent chromatography.
PubMed:Preparative HSCCC isolation of phloroglucinolysis products from grape seed polymeric proanthocyanidins as new powerful antioxidants.
PubMed:Extract from Rumex acetosa L. for prophylaxis of periodontitis: inhibition of bacterial in vitro adhesion and of gingipains of Porphyromonas gingivalis by epicatechin-3-O-(4β→8)-epicatechin-3-O-gallate (procyanidin-B2-Di-gallate).
PubMed:A galloylated dimeric proanthocyanidin from grape seed exhibits dentin biomodification potential.
PubMed:Fast identification of lipase inhibitors in oolong tea by using lipase functionalised Fe3O4 magnetic nanoparticles coupled with UPLC-MS/MS.
PubMed:Tea Flavanols Block Advanced Glycation of Lens Crystallins Induced by Dehydroascorbic Acid.
PubMed:3-O-galloylated procyanidins from Rumex acetosa L. inhibit the attachment of influenza A virus.
PubMed:A preliminary characterization of Aglianico (Vitis vinifera L. cv.) grape proanthocyanidins and evaluation of their reactivity towards salivary proteins.
PubMed:Effect of wine pH and bottle closure on tannins.
PubMed:Human studies on the absorption, distribution, metabolism, and excretion of tea polyphenols.
PubMed:[Chemical constituents of Camellia sinensis var. assamica].
PubMed:Flavan-3-ol-cysteine and acetylcysteine conjugates from edible reagents and the stems of Cynomorium songaricum as potent antioxidants.
PubMed:Antioxidative polyphenols from Nigerian mistletoe Loranthus micranthus (Linn.) parasitizing on Hevea brasiliensis.
PubMed:Compositional and sensory characterization of red wine polymers.
PubMed:Wound-healing plants from TCM: in vitro investigations on selected TCM plants and their influence on human dermal fibroblasts and keratinocytes.
PubMed:Antioxidant phenolic compounds from Pu-erh tea.
PubMed:Comparison of the affinity and selectivity of insoluble fibres and commercial proteins for wine proanthocyanidins.
PubMed:Polyphenolic constituents of Cynomorium songaricum Rupr. and antibacterial effect of polymeric proanthocyanidin on methicillin-resistant Staphylococcus aureus.
PubMed:Capability of Lactobacillus plantarum IFPL935 to catabolize flavan-3-ol compounds and complex phenolic extracts.
PubMed:Development of rapid and simultaneous quantitative method for green tea catechins on the bioanalytical study using UPLC/ESI-MS.
PubMed:Bioactivity-guided fractionation of Phyllanthus orbicularis and identification of the principal anti HSV-2 compounds.
PubMed:Phenolic derivatives from Ruprechtia polystachya and their inhibitory activities on the glucose-6-phosphatase system.
PubMed:Anti-inflammatory and antioxidant components from Hygroryza aristata.
PubMed:Effect of green tea powder (Camellia sinensis L. cv. Benifuuki) particle size on O-methylated EGCG absorption in rats; The Kakegawa Study.
PubMed:Catechin derivatives from Parapiptadenia rigida with in vitro wound-healing properties.
PubMed:Oligomeric proanthocyanidins from Rumex acetosa L. inhibit the attachment of herpes simplex virus type-1.
PubMed:Metabolism of green tea catechins by the human small intestine.
PubMed:Bile acid-binding ability of kaki-tannin from young fruits of persimmon (Diospyros kaki) in vitro and in vivo.
PubMed:Ability of a salivary intrinsically unstructured protein to bind different tannin targets revealed by mass spectrometry.
PubMed:Beta-cyclodextrin/surface plasmon resonance detection system for sensing bitter-astringent taste intensity of green tea catechins.
PubMed:Chemosystematics of tea trees based on tea leaf polyphenols as phenetic markers.
PubMed:Distribution and biosynthesis of flavan-3-ols in Camellia sinensis seedlings and expression of genes encoding biosynthetic enzymes.
PubMed:Comparative study of the phenolic composition of seeds and skins from Carménère and Cabernet Sauvignon grape varieties (Vitis vinifera L.) during ripening.
PubMed:Statistical correlation between flavanolic composition, colour and sensorial parameters in grape seed during ripening.
PubMed:Structural characteristics for superoxide anion radical scavenging and productive activities of green tea polyphenols including proanthocyanidin dimers.
PubMed:Tea catechins' affinity for human cannabinoid receptors.
PubMed:Dietary polyphenols generate nitric oxide from nitrite in the stomach and induce smooth muscle relaxation.
PubMed:Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L.
PubMed:Biobased epicatechin conjugates protect erythrocytes and nontumoral cell lines from H2O2-induced oxidative stress.
PubMed:New seco-anthraquinone glucosides from Rumex nepalensis.
PubMed:Procyanidins from Myrothamnus flabellifolia.
PubMed:New approach for the synthesis and isolation of dimeric procyanidins.
PubMed:Cytotoxic effects of digalloyl dimer procyanidins in human cancer cell lines.
PubMed:Potential anthelmintics: polyphenols from the tea plant Camellia sinensis L. are lethally toxic to Caenorhabditis elegans.
PubMed:The impact of the 67kDa laminin receptor on both cell-surface binding and anti-allergic action of tea catechins.
PubMed:Polymer-like polyphenols of black tea and their lipase and amylase inhibitory activities.
PubMed:Structures of epicatechin gallate trimer and tetramer produced by enzymatic oxidation.
PubMed:Preparative isolation of procyanidins from grape seed extracts by high-speed counter-current chromatography.
PubMed:[Dihydroflavonol glycosides and flavan-3-ols from Bauhinia aurea].
PubMed:Activity of compounds from Chinese herbal medicine Rhodiola kirilowii (Regel) Maxim against HCV NS3 serine protease.
PubMed:Antioxidant effect of Wen-Pi-Tang and its component crude drugs on oxidative stress.
PubMed:Isolation, purification and identification of ellagic acid derivatives, catechins, and procyanidins from the root bark of Anisophyllea dichostyla R. Br.
PubMed:Effect of shading on accumulation of flavonoid compounds in (Vitis vinifera L.) pinot noir fruit and extraction in a model system.
PubMed:Electron-transfer capacity of catechin derivatives and influence on the cell cycle and apoptosis in HT29 cells.
PubMed:Determination of the predominant catechins in Acacia catechu by liquid chromatography/electrospray ionization-mass spectrometry.
PubMed:Antioxidant activity of extract of Rhus oxyacantha root cortex.
PubMed:Studies on nepalese crude drugs. XXVIII. Chemical constituents of Bhote Khair, the underground parts of Eskemukerjea megacarpum HARA.
PubMed:Stereoselective oxidation at C-4 of flavans by the endophytic fungus Diaporthe sp. isolated from a tea plant.
PubMed:Pharmacokinetics of TJ-8117(Onpi-to), a drug for renal failure (II): effects of food, repeated administration and renal failure to plasma concentration of [3H]-(-)epicatechin 3-O-gallate in rats.
PubMed:Conjugation of catechins with cysteine generates antioxidant compounds with enhanced neuroprotective activity.
PubMed:Effect of new antioxidant cysteinyl-flavanol conjugates on skin cancer cells.
PubMed:In vitro antimycotic activity of some plant extracts towards yeast and yeast-like strains.
PubMed:A difference between epigallocatechin-3-gallate and epicatechin-3-gallate on anti-allergic effect is dependent on their distinct distribution to lipid rafts.
PubMed:Pharmacokinetics of TJ-8117 (Onpi-to), a drug for renal failure (I): Plasma concentration, distribution and excretion of [3H]-(-)epicatechin 3-O-gallate in rats and dogs.
PubMed:Anti-genotoxic effects of tea catechins against reactive oxygen species in human lymphoblastoid cells.
PubMed:Tea polyphenols inhibit acetyl-CoA:1-alkyl-sn-glycero-3-phosphocholine acetyltransferase (a key enzyme in platelet-activating factor biosynthesis) and platelet-activating factor-induced platelet aggregation.
PubMed:Cellular toxicity of catechin analogues containing gallate in opossum kidney proximal tubular (OK) cells.
PubMed:(-)-Epicatechin 3-O-gallate ameliorates the damages related to peroxynitrite production by mechanisms distinct from those of other free radical inhibitors.
PubMed:Polyphenolics in grape seeds-biochemistry and functionality.
PubMed:Protective activity of (-)-epicatechin 3-O-gallate against peroxynitrite-mediated renal damage.
PubMed:Pharmacokinetics of (-)-epicatechin-3-O-gallate, an active component of Onpi-to, in rats.
PubMed:Indonesian medicinal plants. XXV. Cancer cell invasion inhibitory effects of chemical constituents in the parasitic plant Scurrula atropurpurea (Loranthaceae).
PubMed:Epimerization of tea catechins and O-methylated derivatives of (-)-epigallocatechin-3-O-gallate: relationship between epimerization and chemical structure.
PubMed:[Studies on non-anthraquinones in Rheum officinale Baill].
PubMed:Direct scavenging of nitric oxide and superoxide by green tea.
PubMed:Effects of epigallocatechin 3-O-gallate on cellular antioxidative system in HepG2 cells.
PubMed:Galloylated catechins and stilbene diglucosides in Vitis vinifera cell suspension cultures.
PubMed:Cysteinyl-flavan-3-ol conjugates from grape procyanidins. Antioxidant and antiproliferative properties.
PubMed:Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.
PubMed:Analytical method of measuring tea catechins in human plasma by solid-phase extraction and HPLC with electrochemical detection.
PubMed:Supercritical fluid extraction of catechins from Cratoxylum prunifolium dyer and subsequent purification by high-speed counter-current chromatography.
PubMed:Inhibitory effects of tea catechins and O-methylated derivatives of (-)-epigallocatechin-3-O-gallate on mouse type IV allergy.
PubMed:Antioxidative activity of green tea treated with radical initiator 2, 2'-azobis(2-amidinopropane) dihydrochloride.
PubMed:Prolyl endopeptidase inhibitory activity of fourteen Kampo formulas and inhibitory constituents of Tokaku-joki-to.
PubMed:Characterization of proanthocyanidins from grape seeds.
PubMed:Green tea polyphenols: novel and potent inhibitors of squalene epoxidase.
PubMed:Inhibition of tyrosinase by green tea components.
PubMed:Isolation from Wen-Pi-Tang of the active principles possessing antioxidation and radical-scavenging activities.
PubMed:[Effects of onpi-to (TJ-8117) and (-)epicatechin-3-O-gallate on the proliferating changes in glomeruli of 5/6 nephrectomized rats].
PubMed:Protective effects of Wen-Pi-Tang against cultured renal epithelial cellular injury.
PubMed:Biotransformation of (-)-epicatechin 3-O-gallate by human intestinal bacteria.
PubMed:Proof that green tea tannin suppresses the increase in the blood methylguanidine level associated with renal failure.
PubMed:Effects of a component of green tea on the proliferation of vascular smooth muscle cells.
PubMed:Inhibitory Effects of Polyphenolic Catechins from Chinese Green Tea on HIV Reverse Transcriptase Activity.
PubMed:Effect of flavan-3-ol tannins purified from Camellia sinensis on lipid peroxidation of rat heart mitochondria.
PubMed:Proanthocyanidins from Quercus petraea Bark.
PubMed:Inhibitory effects of crude drug components on the proliferation of cultured human mesangial cells.
PubMed:Effects of rhubarb tannins on renal function in rats with renal failure.
PubMed:Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
PubMed:Stimulation of monocyte iodination and IL-1 production by tannins and related compounds.
PubMed:Effects of rhubarb tannins on uremic toxins.
 
Notes:
Isol. from tea and numerous other plant spp. inc. rhubarb and grapes
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