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4233-96-9,MFCD00214298
Catalog No.:AA0039YL

4233-96-9 | (2S,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate

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1mg
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5mg
95%
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$65.00   $45.00
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50mg
98%
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100mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0039YL
Chemical Name:
(2S,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate
CAS Number:
4233-96-9
Molecular Formula:
C22H18O11
Molecular Weight:
458.3717
MDL Number:
MFCD00214298
SMILES:
Oc1cc(O)c2c(c1)O[C@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1cc(O)c(c(c1)O)O
Properties
Computed Properties
 
Complexity:
667  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
8  
Rotatable Bond Count:
4  
XLogP3:
1.2  

Literature

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Journal: Xenobiotica; the fate of foreign compounds in biological systems 20120901

Title: Flavonoid-mediated inhibition of SARS coronavirus 3C-like protease expressed in Pichia pastoris.

Journal: Biotechnology letters 20120501

Title: Identification and characterization of proanthocyanidins of 16 members of the Rhododendron genus (Ericaceae) by tandem LC-MS.

Journal: Journal of mass spectrometry : JMS 20120401

Title: Irreversible sediment formation in green tea infusions.

Journal: Journal of food science 20120301

Title: Simultaneous determination of seven bioactive components in Oolong tea Camellia sinensis: quality control by chemical composition and HPLC fingerprints.

Journal: Journal of agricultural and food chemistry 20120111

Title: The effect of enzymatically polymerised polyphenols on CD4 binding and cytokine production in murine splenocytes.

Journal: PloS one 20120101

Title: A facile inhibitor screening of SARS coronavirus N protein using nanoparticle-based RNA oligonucleotide.

Journal: International journal of nanomedicine 20120101

Title: ZnO-ZnS QDs interfacial heterostructure for drug and food delivery application: enhancement of the binding affinities of flavonoid aglycones to bovine serum albumin.

Journal: Nanomedicine : nanotechnology, biology, and medicine 20111201

Title: In vitro anti-uveal melanoma activity of phenolic compounds from the Egyptian medicinal plant Acacia nilotica.

Journal: Fitoterapia 20111201

Title: [Chemical constituents from the roots of Pithecellobium lucidum and their cytotoxic activity].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110701

Title: Anti-inflammatory and antimicrobial effects of nanocatechin in a chronic bacterial prostatitis rat model.

Journal: Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20110401

Title: Mulberry leaf polyphenols possess antiatherogenesis effect via inhibiting LDL oxidation and foam cell formation.

Journal: Journal of agricultural and food chemistry 20110309

Title: Supplementation of green tea catechins in dentifrices suppresses gingival oxidative stress and periodontal inflammation.

Journal: Archives of oral biology 20110101

Title: Stereochemical structure and intermolecular interaction of complexes of (-)-Gallocatechin-3-O-gallate and caffeine.

Journal: Chemical & pharmaceutical bulletin 20110101

Title: Singular features of trypanosomatids' phosphotransferases involved in cell energy management.

Journal: Enzyme research 20110101

Title: Red wine: a source of potent ligands for peroxisome proliferator-activated receptor γ.

Journal: Food & function 20110101

Title: The evaluation of catechins that contain a galloyl moiety as potential HIV-1 integrase inhibitors.

Journal: Clinical immunology (Orlando, Fla.) 20101201

Title: Phosphagen kinases of parasites: unexplored chemotherapeutic targets.

Journal: The Korean journal of parasitology 20101201

Title: An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.

Journal: Journal of natural products 20100723

Title: New inhibitors for expression of IgE receptor on human mast cell.

Journal: Bioorganic & medicinal chemistry letters 20100401

Title: Offset pi-pi interaction in crystal structure of (-)-gallocatechin-3-O-gallate.

Journal: Chemical & pharmaceutical bulletin 20100401

Title: Preventive effects of C-2 epimeric isomers of tea catechins on mouse type I allergy.

Journal: Journal of nutritional science and vitaminology 20100101

Title: Polyphenols of Camellia sinenesis decrease mortality, hepatic injury and generation of cytokines and reactive oxygen and nitrogen species after hemorrhage/resuscitation in rats.

Journal: BMC complementary and alternative medicine 20100101

Title: Green tea catechin, epigallocatechin gallate, suppresses signaling by the dsRNA innate immune receptor RIG-I.

Journal: PloS one 20100101

Title: Green tea polyphenols supplementation and Tai Chi exercise for postmenopausal osteopenic women: safety and quality of life report.

Journal: BMC complementary and alternative medicine 20100101

Title: Borate complexation-assisted field-enhanced sample injection for on-line preconcentration of cis-diol-containing compounds in capillary electrophoresis.

Journal: Talanta 20091215

Title: Tea catechins inhibit hepatocyte growth factor receptor (MET kinase) activity in human colon cancer cells: kinetic and molecular docking studies.

Journal: Journal of medicinal chemistry 20091112

Title: Mulberry leaf extract inhibits vascular smooth muscle cell migration involving a block of small GTPase and Akt/NF-kappaB signals.

Journal: Journal of agricultural and food chemistry 20091014

Title: Degradation and metabolism of catechin, epigallocatechin-3-gallate (EGCG), and related compounds by the intestinal microbiota in the pig cecum model.

Journal: Journal of agricultural and food chemistry 20090909

Title: Effects of tea catechins, epigallocatechin, gallocatechin, and gallocatechin gallate, on bone metabolism.

Journal: Journal of agricultural and food chemistry 20090826

Title: Antiviral effect of epigallocatechin gallate on enterovirus 71.

Journal: Journal of agricultural and food chemistry 20090722

Title: Production and physicochemical properties of recombinant Lactobacillus plantarum tannase.

Journal: Journal of agricultural and food chemistry 20090722

Title: NMR spectroscopic characterization of inclusion complexes comprising cyclodextrins and gallated catechins in aqueous solution: cavity size dependency.

Journal: Magnetic resonance in chemistry : MRC 20090401

Title: The protective effects of green tea extract against L-arginine toxicity to cultured human mesangial cells.

Journal: Journal of Korean medical science 20090101

Title: Green tea extract supplement reduces D-galactosamine-induced acute liver injury by inhibition of apoptotic and proinflammatory signaling.

Journal: Journal of biomedical science 20090101

Title: Green tea polyphenols and Tai Chi for bone health: designing a placebo-controlled randomized trial.

Journal: BMC musculoskeletal disorders 20090101

Title: Tea catechins enhance the mRNA expression of uncoupling protein 1 in rat brown adipose tissue.

Journal: The Journal of nutritional biochemistry 20081201

Title: Role of catechin quinones in the induction of EpRE-mediated gene expression.

Journal: Chemical research in toxicology 20081201

Title: Green tea extracts interfere with the stress-protective activity of PrP and the formation of PrP.

Journal: Journal of neurochemistry 20081001

Title: The impact of the 67kDa laminin receptor on both cell-surface binding and anti-allergic action of tea catechins.

Journal: Archives of biochemistry and biophysics 20080815

Title: Preparative isolation and purification of theaflavins and catechins by high-speed countercurrent chromatography.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080515

Title: Diastereomeric difference of inclusion modes between (-)-epicatechin gallate, (-)-epigallocatechin gallate and (+)-gallocatechin gallate, with beta-cyclodextrin in aqueous solvent.

Journal: Magnetic resonance in chemistry : MRC 20080501

Title: GCG-rich tea catechins are effective in lowering cholesterol and triglyceride concentrations in hyperlipidemic rats.

Journal: Lipids 20080501

Title: Reaction kinetics of degradation and epimerization of epigallocatechin gallate (EGCG) in aqueous system over a wide temperature range.

Journal: Journal of agricultural and food chemistry 20080423

Title: Catechin gallates are NADP+-competitive inhibitors of glucose-6-phosphate dehydrogenase and other enzymes that employ NADP+ as a coenzyme.

Journal: Bioorganic & medicinal chemistry 20080401

Title: [Protection and its mechanism of catechin morphon on hypoxia-reoxygenation [corrected] induced injury in myocardial cells].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080401

Title: Isomeric differentiation of green tea catechins using gas-phase hydrogen/deuterium exchange reactions.

Journal: Journal of the American Society for Mass Spectrometry 20071001

Title: Uniformly-sized, molecularly imprinted polymers for (-)-epigallocatechin gallate, -epicatechin gallate and -gallocatechin gallate by multi-step swelling and polymerization method.

Journal: Journal of chromatography. A 20070713

Title: Effect of molecular structure of phenolic families as hydroxycinnamic acids and catechins on their antioxidant effectiveness in minced fish muscle.

Journal: Journal of agricultural and food chemistry 20070516

Title: Protective effects of EGCg or GCg, a green tea catechin epimer, against postischemic myocardial dysfunction in guinea-pig hearts.

Journal: Life sciences 20070220

Title: Epigallocatechin gallate (EGCG) mimics insulin action on the transcription factor FOXO1a and elicits cellular responses in the presence and absence of insulin.

Journal: Cellular signalling 20070201

Title: Attomole catechins determination by capillary liquid chromatography with electrochemical detection.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20070201

Title: Differential effects of antioxidants on the in vitro invasion, growth and lung metastasis of murine colon cancer cells.

Journal: Biological & pharmaceutical bulletin 20070101

Title: Flavonoid content of U.S. fruits, vegetables, and nuts.

Journal: Journal of agricultural and food chemistry 20061227

Title: Positive inotropic effect of purified green tea catechin derivative in guinea pig hearts: the measurements of cellular Ca2+ and nitric oxide release.

Journal: European journal of pharmacology 20061215

Title: [Separation of isomeric compounds by high speed countercurrent chromatography].

Journal: Se pu = Chinese journal of chromatography 20061101

Title: Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.

Journal: Journal of medicinal chemistry 20060601

Title: Arachidonate 12-lipoxygenases with reference to their selective inhibitors.

Journal: Biochemical and biophysical research communications 20051209

Title: A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate.

Journal: Cellular and molecular life sciences : CMLS 20051201

Title: A novel black tea pigment and two new oxidation products of epigallocatechin-3-O-gallate.

Journal: Journal of agricultural and food chemistry 20050921

Title: Efficiency of foam fractionation for the enrichment of nonpolar compounds from aqueous extracts of plant materials.

Journal: Journal of natural products 20050901

Title: Epigallocatechin-3-gallate suppresses galactose-alpha1,4-galactose-1beta,4-glucose ceramide expression in TNF-alpha stimulated human intestinal epithelial cells through inhibition of MAPKs and NF-kappaB.

Journal: Journal of Korean medical science 20050801

Title: Structure-activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors.

Journal: Bioorganic & medicinal chemistry 20050315

Title: Inhibitory effect of green tea catechins on cysteine proteinases in Porphyromonas gingivalis.

Journal: Oral microbiology and immunology 20040401

Title: 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.

Journal: Journal of agricultural and food chemistry 20031203

Title: Effect of flavan-3-ols on in vitro egg hatching, larval development and viability of infective larvae of Trichostrongylus colubriformis.

Journal: International journal for parasitology 20031201

Title: Phenolic constituents of shea (Vitellaria paradoxa) kernels.

Journal: Journal of agricultural and food chemistry 20031008

Title: Inhibitory effect of green tea polyphenols on membrane-type 1 matrix metalloproteinase, MT1-MMP.

Journal: Biological & pharmaceutical bulletin 20030901

Title: Tea catechins protect against lead-induced ROS formation, mitochondrial dysfunction, and calcium dysregulation in PC12 cells.

Journal: Chemical research in toxicology 20030901

Title: Tea catechin synergies in inhibition of cancer cell proliferation and of a cancer specific cell surface oxidase (ECTO-NOX).

Journal: Pharmacology & toxicology 20030501

Title: Neutrophil restraint by green tea: inhibition of inflammation, associated angiogenesis, and pulmonary fibrosis.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20030415

Title: Direct scavenging of nitric oxide and superoxide by green tea.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20021201

Title: Activity-guided fractionation of green tea extract with antiproliferative activity against human stomach cancer cells.

Journal: Biological & pharmaceutical bulletin 20020901

Title: Study of non-covalent complexation between catechin derivatives and peptides by electrospray ionization mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20020601

Title: Protective activity of green tea against free radical- and glucose-mediated protein damage.

Journal: Journal of agricultural and food chemistry 20020410

Title: [Study on the analytical methods of catechins in tea and green tea polyphenol samples by high performance liquid chromatography].

Journal: Se pu = Chinese journal of chromatography 20010901

Title: Prolyl endopeptidase inhibitors from green tea.

Journal: Archives of pharmacal research 20010801

Title: Degradation of green tea catechins in tea drinks.

Journal: Journal of agricultural and food chemistry 20010101

Title: Green tea and its catechins inhibit breast cancer xenografts.

Journal: Nutrition and cancer 20010101

Title: Zhang LQ, et al. Accumulation of catechins and expression of catechin synthetic genes in Camellia sinensis at different developmental stages. Bot Stud. 2016 Dec;57(1):31.

Title: Zhou H, et al. C-geranylated flavanones from YingDe black tea and their antioxidant and α-glucosidase inhibition activities. Food Chem. 2017 Nov 15;235:227-233.

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Tags:4233-96-9 Molecular Formula|4233-96-9 MDL|4233-96-9 SMILES|4233-96-9 (2S,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate