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Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 861.70 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 581.00 °F. TCC ( 305.00 °C. ) (est)
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| logP (o/w): | 2.670 (est) |
| Soluble in: |
| | water, 36.86 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| 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
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | natural substances and extractives |
| Recommendation for (-)-epicatechin-3-O-gallate usage levels up to: | | | not for fragrance use.
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| Recommendation for (-)-epicatechin-3-O-gallate flavor usage levels up to: |
| | not for flavor use.
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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:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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 | | (-)-epi | catechin gallate | | (-)-epi | catechin-3-gallate | | (-)-epi | catechingallate | | epi | catechol, 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. |
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