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(-)-catechin gallate
(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate

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CAS Number: 130405-40-2Picture of molecule3D/inchi
FDA UNII: 0KT1FO6VO6
Nikkaji Web:J362.848E
MDL:MFCD00214258
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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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.
(-)-Catechin gallate 98%
BOC Sciences
For experimental / research use only.
(-)-Catechin gallate >98%
Odor: characteristic
Use: CG, a minor polyphenolic constituent in green tea, was used to study its cytotoxicity.
Carbosynth
For experimental / research use only.
(-)-Catechin Gallate
ExtraSynthese
For experimental / research use only.
(-)-Catechin Gallate (HPLC) ≥98%
Glentham Life Sciences
(-)-Catechin gallate
Nacalai USA
For experimental / research use only.
(-)-Catechin gallate [(-)-Cg]
Santa Cruz Biotechnology
For experimental / research use only.
(-)-Catechin Gallate ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
(-)-Catechin Gallate ≥98% (HPLC), from green tea
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for (-)-catechin gallate usage levels up to:
 not for fragrance use.
 
Recommendation for (-)-catechin gallate flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6419835
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
[(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Chemidplus:0130405402
 
References:
 [(2S,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):6419835
Pubchem (sid):135275395
 
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):Search
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
 tea green tea
Search Trop Picture
 
Synonyms:
 benzoic acid, 3,4,5-trihydroxy-, (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester
(-)-catechingallate
(2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate)
(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
[(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate
 

Articles:

PubMed:Effect of the type of brewing water on the chemical composition, sensory quality and antioxidant capacity of Chinese teas.
PubMed:Metabolomics analysis reveals the metabolic and functional roles of flavonoids in light-sensitive tea leaves.
PubMed:Tea polyphenols dominate the short-term tea (Camellia sinensis) leaf litter decomposition.
PubMed:Ultraviolet B (UVB) Photosensitivities of Tea Catechins and the Relevant Chemical Conversions.
PubMed:Impact of Clonal Variability on Phenolics and Radical Scavenging Activity of Grapes and Wines: A Study on the Recently Developed Merlot and Cabernet Franc Clones (Vitis vinifera L.).
PubMed:Inhibitory Effects of Eight Green Tea Catechins on Cytochrome P450 1A2, 2C9, 2D6, and 3A4 Activities.
PubMed:Mineral and metabolic profiles in tea leaves and flowers during flower development.
PubMed:Vitamin A or E and a catechin synergize as vaccine adjuvant to enhance immune responses in mice by induction of early interleukin-15 but not interleukin-1β responses.
PubMed:Screening and Toxicity Analysis of Catechin Isomers Against FemA Protein.
PubMed:Growth inhibition and apoptosis in cancer cells induced by polyphenolic compounds of Acacia hydaspica: Involvement of multiple signal transduction pathways.
PubMed:Association of Catechin Molecules in Water: Quantitative Binding Study and Complex Structure Analysis.
PubMed:Determination and quality evaluation of green tea extracts through qualitative and quantitative analysis of multi-components by single marker (QAMS).
PubMed:Neuroprotection by epigallo catechin gallate against bupivacaine anesthesia induced toxicity involves modulation of PI3/Akt/PTEN signalling in N2a and SH-SY5Y cells.
PubMed:Catechin inhibition of influenza neuraminidase and its molecular basis with mass spectrometry.
PubMed:In vitro effects of some flavonoids and phenolic acids on human pyruvate kinase isoenzyme M2.
PubMed:Structure-dependent inhibitory effects of green tea catechins on insulin secretion from pancreatic β-cells.
PubMed:Polyphenols: well beyond the antioxidant capacity: gallic acid and related compounds as neuroprotective agents: you are what you eat!
PubMed:Optimization of subcritical water extraction of flavanols from green tea leaves.
PubMed:Galloyl moieties enhance the dentin biomodification potential of plant-derived catechins.
PubMed:In vitro inhibition of fatty acid synthase by 1,2,3,4,6-penta-O-galloyl-β-D-glucose plays a vital role in anti-tumour activity.
PubMed:UHPLC determination of catechins for the quality control of green tea.
PubMed:Green tea catechins quench the fluorescence of bacteria-conjugated Alexa fluor dyes.
PubMed:Chromenylchalcones showing cytotoxicity on human colon cancer cell lines and in silico docking with aurora kinases.
PubMed:Effects of catechin polyphenols and preparations from the plant-parasitic nematode Heterodera glycines on protease activity and behaviour in three nematode species.
PubMed:Epigallocatechin-3-gallate is a potent phytochemical inhibitor of intimal hyperplasia in the wire-injured carotid artery.
PubMed:Epigallocatechin Gallate (EGCG) is the most effective cancer chemopreventive polyphenol in green tea.
PubMed:Role of catechins in the antioxidant capacity of an active film containing green tea, green coffee, and grapefruit extracts.
PubMed:Inhibitory effects of daiokanzoto (da-huang-gan-cao-tang) on p-glycoprotein.
PubMed:Grape seed and tea extracts and catechin 3-gallates are potent inhibitors of α-amylase and α-glucosidase activity.
PubMed:Identification and characterization of proanthocyanidins of 16 members of the Rhododendron genus (Ericaceae) by tandem LC-MS.
PubMed:Engineering the production of major catechins by Escherichia coli carrying metabolite genes of Camellia sinensis.
PubMed:A facile inhibitor screening of SARS coronavirus N protein using nanoparticle-based RNA oligonucleotide.
PubMed:Dietary green and white teas suppress UDP-glucuronosyltransferase UGT2B17 mediated testosterone glucuronidation.
PubMed:Epicatechin-3-O-(3″-O-methyl)-gallate content in various tea cultivars (Camellia sinensis L.) and its in vitro inhibitory effect on histamine release.
PubMed:Survey of antioxidant capacity and phenolic composition of blueberry, blackberry, and strawberry in Nanjing.
PubMed:[Study on extraction process of available components of tea].
PubMed:Analysis of the mechanism of inhibition of human matrix metalloproteinase 7 (MMP-7) activity by green tea catechins.
PubMed:Configurational studies of complexes of various tea catechins and caffeine in crystal state.
PubMed:Effect of girdling at various positions of 'Huang Zhi Xiang' tea tree (Camellia sinensis) on the contents of catechins and starch in fresh leaf.
PubMed:Epicatechin gallate and catechin gallate are superior to epigallocatechin gallate in growth suppression and anti-inflammatory activities in pancreatic tumor cells.
PubMed:The evaluation of catechins that contain a galloyl moiety as potential HIV-1 integrase inhibitors.
PubMed:Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals.
PubMed:Integrated ligand and structure based studies of flavonoids as fatty acid biosynthesis inhibitors of Plasmodium falciparum.
PubMed:Comparison of the nutrient and chemical contents of traditional Korean Chungtaejeon and green teas.
PubMed:Dietary flavonoids activate the constitutive androstane receptor (CAR).
PubMed:Green tea catechin EGCG inhibits ileal apical sodium bile acid transporter ASBT.
PubMed:Effect of girdling on levels of catechins in fresh leaf in relation to quality of 'Huang Zhi Xiang' Oolong' tea.
PubMed:Induction of apoptosis by immature plum in human hepatocellular carcinoma.
PubMed:Mitochondrial alterations in aging rat brain: effective role of (-)-epigallo catechin gallate.
PubMed:(-)Epigallocatechin-3-gallate inhibits the spontaneous firing of rat locus coeruleus neuron.
PubMed:Efficient procedure for isolating methylated catechins from green tea and effective simultaneous analysis of ten catechins, three purine alkaloids, and gallic acid in tea by high-performance liquid chromatography with diode array detection.
PubMed:Comparative neuroprotective properties of stilbene and catechin analogs: action via a plasma membrane receptor site?
PubMed:Determination of extractability of pine bark using supercritical CO(2) extraction and different solvents: optimization and prediction.
PubMed:A new phenylpropanoid derivative of catechin from the needles of Taxus cuspidata.
PubMed:Antioxidants from steamed used tea leaves and their reaction behavior.
PubMed:Total antioxidant capacity and content of flavonoids and other phenolic compounds in canihua (Chenopodium pallidicaule): an Andean pseudocereal.
PubMed:Multifunctional effects of green tea catechins on prevention of the metabolic syndrome.
PubMed:Tea catechins enhance the mRNA expression of uncoupling protein 1 in rat brown adipose tissue.
PubMed:Cytotoxic effects of digalloyl dimer procyanidins in human cancer cell lines.
PubMed:The impact of the 67kDa laminin receptor on both cell-surface binding and anti-allergic action of tea catechins.
PubMed:Catechin gallates are NADP+-competitive inhibitors of glucose-6-phosphate dehydrogenase and other enzymes that employ NADP+ as a coenzyme.
PubMed:Bioactivity-guided isolation of the active compounds from Rosa nutkana and quantitative analysis of ascorbic acid by HPLC.
PubMed:Identification of major phenolic compounds of Chinese water chestnut and their antioxidant activity.
PubMed:Isomeric differentiation of green tea catechins using gas-phase hydrogen/deuterium exchange reactions.
PubMed:Epigallocatechin gallate-induced apoptosis does not affect adipocyte conversion of preadipocytes.
PubMed:In vitro cytotoxicity of (-)-catechin gallate, a minor polyphenol in green tea.
PubMed:Mass spectrometry-based systems approach for identification of inhibitors of Plasmodium falciparum fatty acid synthase.
PubMed:Effect of molecular structure of phenolic families as hydroxycinnamic acids and catechins on their antioxidant effectiveness in minced fish muscle.
PubMed:Synergistic effects of multiple treatments, and both DNA and RNA direct bindings on, green tea catechins.
PubMed:Neuroprotective effects of natural products: interaction with intracellular kinases, amyloid peptides and a possible role for transthyretin.
PubMed:Phenolic phytochemicals derived from red pine (Pinus densiflora) inhibit the invasion and migration of SK-Hep-1 human hepatocellular carcinoma cells.
PubMed:Attomole catechins determination by capillary liquid chromatography with electrochemical detection.
PubMed:Flavonoid content of U.S. fruits, vegetables, and nuts.
PubMed:Synthesis and preliminary anticancer activity studies of C4 and C8-modified derivatives of catechin gallate (CG) and epicatechin gallate (ECG).
PubMed:Inhibition of HuR and MMP-9 expression in macrophage-differentiated HL-60 myeloid leukemia cells by green tea polyphenol EGCg.
PubMed:Enzymatic O-methylation of flavanols changes lag time, propagation rate, and total oxidation during in vitro model triacylglycerol-rich lipoprotein oxidation.
PubMed:Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.
PubMed:Inhibition of fatty acid synthase by polyphenols.
PubMed:Potentiation of catechin gallate-mediated sensitization of Staphylococcus aureus to oxacillin by nongalloylated catechins.
PubMed:Rational design of anticytoadherence inhibitors for Plasmodium falciparum based on the crystal structure of human intercellular adhesion molecule 1.
PubMed:Neuroprotective effects of green and black teas and their catechin gallate esters against beta-amyloid-induced toxicity.
PubMed:Catechin derivatives: specific inhibitor for caspases-3, 7 and 2, and the prevention of apoptosis at the cell and animal levels.
PubMed:Inhibition of growth, induction of apoptosis and alteration of gene expression by tea polyphenols in the highly metastatic human lung cancer cell line NCI-H460.
PubMed:Inhibitory effects of catechin gallates on o-methyltranslation of protocatechuic acid in rat liver cytosolic preparations and cultured hepatocytes.
PubMed:Separation of catechin constituents from five tea cultivars using high-speed counter-current chromatography.
PubMed:Determination of proanthocyanidins in fresh grapes and grape products using liquid chromatography with mass spectrometric detection.
PubMed:[Determination of catechins and caffeine in tea and tea beverages by high-performance liquid chromatography].
PubMed:Structural analysis of catechin derivatives as mammalian DNA polymerase inhibitors.
PubMed:Novel inhibitors of fatty-acid synthase from green tea (Camellia sinensis Xihu Longjing) with high activity and a new reacting site.
PubMed:Dietary gallate esters of tea catechins reduce deposition of visceral fat, hepatic triacylglycerol, and activities of hepatic enzymes related to fatty acid synthesis in rats.
PubMed:Antimutagenic properties of green tea.
PubMed:Tea catechins with a galloyl moiety suppress postprandial hypertriacylglycerolemia by delaying lymphatic transport of dietary fat in rats.
PubMed:Differential in vitro cytotoxicity of (-)-epicatechin gallate (ECG) to cancer and normal cells from the human oral cavity.
PubMed:Tannins and catechin gallate mediate the vasorelaxant effect of Arbutus unedo on the rat isolated aorta.
PubMed:New apoptosis cascade mediated by lysosomal enzyme and its protection by epigallo-catechin gallate.
PubMed:Myricetin, quercetin and catechin-gallate inhibit glucose uptake in isolated rat adipocytes.
PubMed:Determination of catechins and catechin gallates in tissues by liquid chromatography with coulometric array detection and selective solid phase extraction.
PubMed:Direct enantioseparation of catechin and epicatechin in tea drinks by 6-O-alpha-D-glucosyl-beta-cyclodextrin-modified micellar electrokinetic chromatography.
PubMed:Study of the green tea polyphenols catechin-3-gallate (CG) and epicatechin-3-gallate (ECG) as proteasome inhibitors.
PubMed:Comparison of antioxidant activity and bioavailability of tea epicatechins with their epimers.
PubMed:Flavonoids from Argentine Tagetes (Asteraceae) with antimicrobial activity.
PubMed:Modulation of beta-lactam resistance in Staphylococcus aureus by catechins and gallates.
PubMed:Inhibitory effect of green tea catechins on cysteine proteinases in Porphyromonas gingivalis.
PubMed:Vascular actions of the polyphenolic catechin gallate EGCG: endothelium-dependent contraction and relaxation.
PubMed:Anti-Trypanosoma cruzi activity of green tea (Camellia sinensis) catechins.
PubMed:Proanthocyanidin composition in the seed coat of lentils (Lens culinaris L.).
PubMed:Heat-epimerized tea catechins rich in gallocatechin gallate and catechin gallate are more effective to inhibit cholesterol absorption than tea catechins rich in epigallocatechin gallate and epicatechin gallate.
PubMed:Effect of flavan-3-ols on in vitro egg hatching, larval development and viability of infective larvae of Trichostrongylus colubriformis.
PubMed:Effects of flavonoids on vascular smooth muscle of the isolated rat thoracic aorta.
PubMed:Green tea catechins as a BACE1 (beta-secretase) inhibitor.
PubMed:Inhibition of proliferation of human cancer cells and cyclooxygenase enzymes by anthocyanidins and catechins.
PubMed:Determination of proanthocyanidins in grape products by liquid chromatography/mass spectrometric detection under low collision energy.
PubMed:Complex effects of different green tea catechins on human platelets.
PubMed:Inhibitory effects of green tea catechins on the activity of human matrix metalloproteinase 7 (matrilysin).
PubMed:Selective inhibition of ADAMTS-1, -4 and -5 by catechin gallate esters.
PubMed:[Study on the analytical methods of catechins in tea and green tea polyphenol samples by high performance liquid chromatography].
PubMed:Effects of catechins on vascular tone in rat thoracic aorta with endothelium.
PubMed:Effects of plant-derived phenols on rat liver cytochrome P450 2B1 activity.
PubMed:Inhibition of aromatase activity by green tea extract catechins and their endocrinological effects of oral administration in rats.
PubMed:Inhibition of the PDGF beta-receptor tyrosine phosphorylation and its downstream intracellular signal transduction pathway in rat and human vascular smooth muscle cells by different catechins.
PubMed:Effects of dietary antioxidants on human DNA ex vivo.
PubMed:Green tea and its catechins inhibit breast cancer xenografts.
PubMed:Green tea catechins inhibit vascular endothelial growth factor receptor phosphorylation.
PubMed:Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase.
PubMed:Hydrogen peroxide and flavan-3-ols in storage roots of cassava (Manihot esculenta crantz) during postharvest deterioration.
PubMed:Effects of heat processing and storage on flavanols and sensory qualities of green tea beverage.
PubMed:Biochemical characterization of casein kinase II as a protein kinase responsible for stimulation of HIV-1 protease in vitro.
PubMed:Determination of catechins in human urine subsequent to tea ingestion by high-performance liquid chromatography with electrochemical detection.
PubMed:Comparative analysis of tea catechins and theaflavins by high-performance liquid chromatography and capillary electrophoresis.
PubMed:Effects of green tea catechins on membrane fluidity.
PubMed:Inhibition of aberrant proliferation and induction of apoptosis in pre-neoplastic human mammary epithelial cells by natural phytochemicals.
PubMed:A new process of cancer prevention mediated through inhibition of tumor necrosis factor alpha expression.
PubMed:Mechanism of catechin chemiluminescence in the presence of active oxygen.
PubMed:Polyphenolic flavanols as scavengers of aqueous phase radicals and as chain-breaking antioxidants.
PubMed:Plant polyphenols: free radical scavengers or chain-breaking antioxidants?
PubMed:[Relationship between the anti-hemolysin activity and the structure of catechins and theaflavins].
PubMed:Detection and chemical identification of natural bio-antimutagens. A case of the green tea factor.
 
Notes:
None found
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