Home Other Building Blocks (2S,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate

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

CAS No.:
4233-96-9
Catalog Number:
AG003A1D
Molecular Formula:
C22H18O11
Molecular Weight:
458.3717
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$97
- +
5mg
99%
1 week
United States
$157
- +
10mg
99%
1 week
United States
$207
- +
25mg
99%
1 week
United States
$357
- +
Product Description
Catalog Number:
AG003A1D
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
IUPAC Name:
[(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
InChI:
InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21+/m1/s1
InChI Key:
WMBWREPUVVBILR-NQIIRXRSSA-N
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
UNII:
IRW3C4Y31Q
Properties
Complexity:
667  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
458.085g/mol
Formal Charge:
0
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
8  
Isotope Atom Count:
0
Molecular Weight:
458.375g/mol
Monoisotopic Mass:
458.085g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
197A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.2  
Literature
Title Journal
Naturally occurring flavonoids as inhibitors of purified cytosolic glutathione S-transferase. Xenobiotica; the fate of foreign compounds in biological systems 20120901
Flavonoid-mediated inhibition of SARS coronavirus 3C-like protease expressed in Pichia pastoris. Biotechnology letters 20120501
Identification and characterization of proanthocyanidins of 16 members of the Rhododendron genus (Ericaceae) by tandem LC-MS. Journal of mass spectrometry : JMS 20120401
Irreversible sediment formation in green tea infusions. Journal of food science 20120301
Simultaneous determination of seven bioactive components in Oolong tea Camellia sinensis: quality control by chemical composition and HPLC fingerprints. Journal of agricultural and food chemistry 20120111
The effect of enzymatically polymerised polyphenols on CD4 binding and cytokine production in murine splenocytes. PloS one 20120101
A facile inhibitor screening of SARS coronavirus N protein using nanoparticle-based RNA oligonucleotide. International journal of nanomedicine 20120101
ZnO-ZnS QDs interfacial heterostructure for drug and food delivery application: enhancement of the binding affinities of flavonoid aglycones to bovine serum albumin. Nanomedicine : nanotechnology, biology, and medicine 20111201
In vitro anti-uveal melanoma activity of phenolic compounds from the Egyptian medicinal plant Acacia nilotica. Fitoterapia 20111201
[Chemical constituents from the roots of Pithecellobium lucidum and their cytotoxic activity]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110701
Anti-inflammatory and antimicrobial effects of nanocatechin in a chronic bacterial prostatitis rat model. Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20110401
Mulberry leaf polyphenols possess antiatherogenesis effect via inhibiting LDL oxidation and foam cell formation. Journal of agricultural and food chemistry 20110309
Supplementation of green tea catechins in dentifrices suppresses gingival oxidative stress and periodontal inflammation. Archives of oral biology 20110101
Stereochemical structure and intermolecular interaction of complexes of (-)-Gallocatechin-3-O-gallate and caffeine. Chemical & pharmaceutical bulletin 20110101
Singular features of trypanosomatids' phosphotransferases involved in cell energy management. Enzyme research 20110101
Red wine: a source of potent ligands for peroxisome proliferator-activated receptor γ. Food & function 20110101
The evaluation of catechins that contain a galloyl moiety as potential HIV-1 integrase inhibitors. Clinical immunology (Orlando, Fla.) 20101201
Phosphagen kinases of parasites: unexplored chemotherapeutic targets. The Korean journal of parasitology 20101201
An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds. Journal of natural products 20100723
New inhibitors for expression of IgE receptor on human mast cell. Bioorganic & medicinal chemistry letters 20100401
Offset pi-pi interaction in crystal structure of (-)-gallocatechin-3-O-gallate. Chemical & pharmaceutical bulletin 20100401
Preventive effects of C-2 epimeric isomers of tea catechins on mouse type I allergy. Journal of nutritional science and vitaminology 20100101
Polyphenols of Camellia sinenesis decrease mortality, hepatic injury and generation of cytokines and reactive oxygen and nitrogen species after hemorrhage/resuscitation in rats. BMC complementary and alternative medicine 20100101
Green tea catechin, epigallocatechin gallate, suppresses signaling by the dsRNA innate immune receptor RIG-I. PloS one 20100101
Green tea polyphenols supplementation and Tai Chi exercise for postmenopausal osteopenic women: safety and quality of life report. BMC complementary and alternative medicine 20100101
Borate complexation-assisted field-enhanced sample injection for on-line preconcentration of cis-diol-containing compounds in capillary electrophoresis. Talanta 20091215
Tea catechins inhibit hepatocyte growth factor receptor (MET kinase) activity in human colon cancer cells: kinetic and molecular docking studies. Journal of medicinal chemistry 20091112
Mulberry leaf extract inhibits vascular smooth muscle cell migration involving a block of small GTPase and Akt/NF-kappaB signals. Journal of agricultural and food chemistry 20091014
Degradation and metabolism of catechin, epigallocatechin-3-gallate (EGCG), and related compounds by the intestinal microbiota in the pig cecum model. Journal of agricultural and food chemistry 20090909
Effects of tea catechins, epigallocatechin, gallocatechin, and gallocatechin gallate, on bone metabolism. Journal of agricultural and food chemistry 20090826
Antiviral effect of epigallocatechin gallate on enterovirus 71. Journal of agricultural and food chemistry 20090722
Production and physicochemical properties of recombinant Lactobacillus plantarum tannase. Journal of agricultural and food chemistry 20090722
NMR spectroscopic characterization of inclusion complexes comprising cyclodextrins and gallated catechins in aqueous solution: cavity size dependency. Magnetic resonance in chemistry : MRC 20090401
The protective effects of green tea extract against L-arginine toxicity to cultured human mesangial cells. Journal of Korean medical science 20090101
Green tea extract supplement reduces D-galactosamine-induced acute liver injury by inhibition of apoptotic and proinflammatory signaling. Journal of biomedical science 20090101
Green tea polyphenols and Tai Chi for bone health: designing a placebo-controlled randomized trial. BMC musculoskeletal disorders 20090101
Tea catechins enhance the mRNA expression of uncoupling protein 1 in rat brown adipose tissue. The Journal of nutritional biochemistry 20081201
Role of catechin quinones in the induction of EpRE-mediated gene expression. Chemical research in toxicology 20081201
Green tea extracts interfere with the stress-protective activity of PrP and the formation of PrP. Journal of neurochemistry 20081001
The impact of the 67kDa laminin receptor on both cell-surface binding and anti-allergic action of tea catechins. Archives of biochemistry and biophysics 20080815
Preparative isolation and purification of theaflavins and catechins by high-speed countercurrent chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080515
Diastereomeric difference of inclusion modes between (-)-epicatechin gallate, (-)-epigallocatechin gallate and (+)-gallocatechin gallate, with beta-cyclodextrin in aqueous solvent. Magnetic resonance in chemistry : MRC 20080501
GCG-rich tea catechins are effective in lowering cholesterol and triglyceride concentrations in hyperlipidemic rats. Lipids 20080501
Reaction kinetics of degradation and epimerization of epigallocatechin gallate (EGCG) in aqueous system over a wide temperature range. Journal of agricultural and food chemistry 20080423
Catechin gallates are NADP+-competitive inhibitors of glucose-6-phosphate dehydrogenase and other enzymes that employ NADP+ as a coenzyme. Bioorganic & medicinal chemistry 20080401
[Protection and its mechanism of catechin morphon on hypoxia-reoxygenation [corrected] induced injury in myocardial cells]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080401
Isomeric differentiation of green tea catechins using gas-phase hydrogen/deuterium exchange reactions. Journal of the American Society for Mass Spectrometry 20071001
Uniformly-sized, molecularly imprinted polymers for (-)-epigallocatechin gallate, -epicatechin gallate and -gallocatechin gallate by multi-step swelling and polymerization method. Journal of chromatography. A 20070713
Effect of molecular structure of phenolic families as hydroxycinnamic acids and catechins on their antioxidant effectiveness in minced fish muscle. Journal of agricultural and food chemistry 20070516
Protective effects of EGCg or GCg, a green tea catechin epimer, against postischemic myocardial dysfunction in guinea-pig hearts. Life sciences 20070220
Epigallocatechin gallate (EGCG) mimics insulin action on the transcription factor FOXO1a and elicits cellular responses in the presence and absence of insulin. Cellular signalling 20070201
Attomole catechins determination by capillary liquid chromatography with electrochemical detection. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20070201
Differential effects of antioxidants on the in vitro invasion, growth and lung metastasis of murine colon cancer cells. Biological & pharmaceutical bulletin 20070101
Flavonoid content of U.S. fruits, vegetables, and nuts. Journal of agricultural and food chemistry 20061227
Positive inotropic effect of purified green tea catechin derivative in guinea pig hearts: the measurements of cellular Ca2+ and nitric oxide release. European journal of pharmacology 20061215
[Separation of isomeric compounds by high speed countercurrent chromatography]. Se pu = Chinese journal of chromatography 20061101
Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids. Journal of medicinal chemistry 20060601
Arachidonate 12-lipoxygenases with reference to their selective inhibitors. Biochemical and biophysical research communications 20051209
A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate. Cellular and molecular life sciences : CMLS 20051201
A novel black tea pigment and two new oxidation products of epigallocatechin-3-O-gallate. Journal of agricultural and food chemistry 20050921
Efficiency of foam fractionation for the enrichment of nonpolar compounds from aqueous extracts of plant materials. Journal of natural products 20050901
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 of Korean medical science 20050801
Structure-activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors. Bioorganic & medicinal chemistry 20050315
Inhibitory effect of green tea catechins on cysteine proteinases in Porphyromonas gingivalis. Oral microbiology and immunology 20040401
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 of agricultural and food chemistry 20031203
Effect of flavan-3-ols on in vitro egg hatching, larval development and viability of infective larvae of Trichostrongylus colubriformis. International journal for parasitology 20031201
Phenolic constituents of shea (Vitellaria paradoxa) kernels. Journal of agricultural and food chemistry 20031008
Inhibitory effect of green tea polyphenols on membrane-type 1 matrix metalloproteinase, MT1-MMP. Biological & pharmaceutical bulletin 20030901
Tea catechins protect against lead-induced ROS formation, mitochondrial dysfunction, and calcium dysregulation in PC12 cells. Chemical research in toxicology 20030901
Tea catechin synergies in inhibition of cancer cell proliferation and of a cancer specific cell surface oxidase (ECTO-NOX). Pharmacology & toxicology 20030501
Neutrophil restraint by green tea: inhibition of inflammation, associated angiogenesis, and pulmonary fibrosis. Journal of immunology (Baltimore, Md. : 1950) 20030415
Direct scavenging of nitric oxide and superoxide by green tea. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20021201
Activity-guided fractionation of green tea extract with antiproliferative activity against human stomach cancer cells. Biological & pharmaceutical bulletin 20020901
Study of non-covalent complexation between catechin derivatives and peptides by electrospray ionization mass spectrometry. Journal of mass spectrometry : JMS 20020601
Protective activity of green tea against free radical- and glucose-mediated protein damage. Journal of agricultural and food chemistry 20020410
[Study on the analytical methods of catechins in tea and green tea polyphenol samples by high performance liquid chromatography]. Se pu = Chinese journal of chromatography 20010901
Prolyl endopeptidase inhibitors from green tea. Archives of pharmacal research 20010801
Degradation of green tea catechins in tea drinks. Journal of agricultural and food chemistry 20010101
Green tea and its catechins inhibit breast cancer xenografts. Nutrition and cancer 20010101
Properties