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14937-32-7,MFCD03788860
Catalog No.:AA00AOGO

14937-32-7 | 1,2,3,4,6-Penta-O-galloyl-beta-D-glucopyranose

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1mg
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5mg
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10mg
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50mg
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250mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00AOGO
Chemical Name:
1,2,3,4,6-Penta-O-galloyl-beta-D-glucopyranose
CAS Number:
14937-32-7
Molecular Formula:
C41H32O26
Molecular Weight:
940.6772
MDL Number:
MFCD03788860
SMILES:
O=C(c1cc(O)c(c(c1)O)O)O[C@@H]1OC(COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([C@@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O
Properties
Computed Properties
 
Complexity:
1680  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Heavy Atom Count:
67  
Hydrogen Bond Acceptor Count:
26  
Hydrogen Bond Donor Count:
15  
Rotatable Bond Count:
16  
XLogP3:
3.6  

Downstream Synthesis Route

[1]ChemicalandPharmaceuticalBulletin,1980,vol.28,p.2850-2852

[1]Chemicalandpharmaceuticalbulletin,1989,vol.37,p.1919-1921

[2]Chemicalandpharmaceuticalbulletin,1989,vol.37,p.1919-1921

[1]LiebigsAnnalenderChemie,1984,p.929-938

[2]Bioscience,BiotechnologyandBiochemistry,2001,vol.65,p.1869-1871

[3]PhytochemicalAnalysis,2013,vol.24,p.424-435

[1]Tetrahedron,1997,vol.53,p.10725-10732

[2]Patent:US9096501,2015,B2.Locationinpatent:Page/Pagecolumn61

[3]AngewandteChemie-InternationalEdition,2015,vol.54,p.8217-8221    Angew.Chem.,2015,vol.127,p.8335-8339,5

[4]JournalofMedicinalChemistry,2006,vol.49,p.2829-2837

[5]ACSMedicinalChemistryLetters,2012,vol.3,p.631-636,6

[6]JournalofMedicinalChemistry,2014,vol.57,p.4805-4818

[1]Phytochemistry,1998,vol.49,p.327-332

Literature

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Journal: Biochemical and biophysical research communications 20120803

Title: A review of animal and human studies for management of benign prostatic hyperplasia with natural products: perspective of new pharmacological agents.

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Title: Aqueous Extract of Paeonia suffruticosa Inhibits Migration and Metastasis of Renal Cell Carcinoma Cells via Suppressing VEGFR-3 Pathway.

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Title: Involvement of iron in biofilm formation by Staphylococcus aureus.

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Title: A gallotannin-rich fraction from Caesalpinia spinosa (Molina) Kuntze displays cytotoxic activity and raises sensitivity to doxorubicin in a leukemia cell line.

Journal: BMC complementary and alternative medicine 20120101

Title: Gelatin tannate reduces the proinflammatory effects of lipopolysaccharide in human intestinal epithelial cells.

Journal: Clinical and experimental gastroenterology 20120101

Title: Insulin receptor signaling activated by penta-O-galloyl-α-D: -glucopyranose induces p53 and apoptosis in cancer cells.

Journal: Apoptosis : an international journal on programmed cell death 20110901

Title: Pharmacological evaluation of insulin mimetic novel suppressors of PEPCK gene transcription from Paeoniae Rubra Radix.

Journal: Journal of ethnopharmacology 20110901

Title: The genome-wide expression profile of 1,2,3,4,6-penta-O-galloyl-β-D-glucose-treated MDA-MB-231 breast cancer cells: molecular target on cancer metabolism.

Journal: Molecules and cells 20110831

Title: 1,2,3,4,6-penta-O-galloyl-β-D-glucose, quercetin, curcumin and lycopene induce cell-cycle arrest in MDA-MB-231 and BT474 cells through downregulation of Skp2 protein.

Journal: Journal of agricultural and food chemistry 20110622

Title: Oral administration of penta-O-galloyl-β-D-glucose suppresses triple-negative breast cancer xenograft growth and metastasis in strong association with JAK1-STAT3 inhibition.

Journal: Carcinogenesis 20110601

Title: 1,2,3,4,6-Penta-O-galloyl-beta-D-glucose reduces renal crystallization and oxidative stress in a hyperoxaluric rat model.

Journal: Kidney international 20110301

Title: Conformation of the tridimensional structure of 1,2,3,4,6-pentagalloyl-β-D-glucopyranose (PGG) by (1)H NMR, NOESY and theoretical study and membrane interaction in a simulated phospholipid bilayer: a first insight.

Journal: Magnetic resonance in chemistry : MRC 20110301

Title: A novel small molecule 1,2,3,4,6-penta-O-galloyl-α-D-glucopyranose mimics the antiplatelet actions of insulin.

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Title: Oenothera paradoxa defatted seeds extract and its bioactive component penta-O-galloyl-β-D-glucose decreased production of reactive oxygen species and inhibited release of leukotriene B4, interleukin-8, elastase, and myeloperoxidase in human neutrophils.

Journal: Journal of agricultural and food chemistry 20100922

Title: Intestinal alpha-glucosidase inhibitory activity and toxicological evaluation of Nymphaea stellata flowers extract.

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Journal: Journal of Alzheimer's disease : JAD 20100101

Title: Effect of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose on elastase and hyaluronidase activities and its type II collagen expression.

Journal: Acta poloniae pharmaceutica 20100101

Title: 1,2,3,4,6-penta-O-galloyl-beta-D-glucose protects splenocytes against radiation-induced apoptosis in murine splenocytes.

Journal: Biological & pharmaceutical bulletin 20100101

Title: Penta-O-galloyl-beta-D-glucose induces G1 arrest and DNA replicative S-phase arrest independently of cyclin-dependent kinase inhibitor 1A, cyclin-dependent kinase inhibitor 1B and P53 in human breast cancer cells and is orally active against triple negative xenograft growth.

Journal: Breast cancer research : BCR 20100101

Title: 1,2,3,4,6-Penta-O-galloly-beta-D-glucose suppresses hypoxia-induced accumulation of hypoxia-inducible factor-1α and signaling in LNCaP prostate cancer cells.

Journal: Biological & pharmaceutical bulletin 20100101

Title: Polyphenol-stabilized tubular elastin scaffolds for tissue engineered vascular grafts.

Journal: Tissue engineering. Part A 20091001

Title: Suppression of thymus- and activation-regulated chemokine (TARC/CCL17) production by 1,2,3,4,6-penta-O-galloyl-beta-D-glucose via blockade of NF-kappaB and STAT1 activation in the HaCaT cells.

Journal: Biochemical and biophysical research communications 20090911

Title: [Chemical constituents from roots of Distylium myricoides].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090901

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Title: Melanogenesis inhibition by gallotannins from Chinese galls in B16 mouse melanoma cells.

Journal: Biological & pharmaceutical bulletin 20090801

Title: A traditional medicinal herb Paeonia suffruticosa and its active constituent 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose have potent anti-aggregation effects on Alzheimer's amyloid beta proteins in vitro and in vivo.

Journal: Journal of neurochemistry 20090601

Title: Penta-O-galloyl-beta-D-glucose induces S- and G(1)-cell cycle arrests in prostate cancer cells targeting DNA replication and cyclin D1.

Journal: Carcinogenesis 20090501

Title: Penta-O-galloyl-beta-D-glucose suppresses prostate cancer bone metastasis by transcriptionally repressing EGF-induced MMP-9 expression.

Journal: Journal of agricultural and food chemistry 20090422

Title: 1,2,3,4,6-penta-O-galloyl-beta-D-glucose attenuates renal cell migration, hyaluronan expression, and crystal adhesion.

Journal: European journal of pharmacology 20090315

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Journal: Journal of cosmetic science 20090101

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Journal: Journal of agricultural and food chemistry 20080910

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Journal: Planta medica 20080901

Title: Penta-1,2,3,4,6-O-galloyl-beta-D-glucose induces p53 and inhibits STAT3 in prostate cancer cells in vitro and suppresses prostate xenograft tumor growth in vivo.

Journal: Molecular cancer therapeutics 20080901

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Journal: Phytotherapy research : PTR 20080801

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Journal: Phytotherapy research : PTR 20080401

Title: [Determination of 1, 2, 3, 4, 6-penta-O-galloyl-D-glucose in forty four kinds of Chinese traditional medicines by HPLC].

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Journal: Canadian journal of physiology and pharmacology 20070901

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Journal: Neuroscience letters 20020809

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Title: Viswanatha GL, et al. Alleviation of transient global ischemia/reperfusion-induced brain injury in rats with 1,2,3,4,6-penta-O-galloyl-β-d-glucopyranose isolated from Mangifera indica. Eur J Pharmacol. 2013 Nov 15;720(1-3):286-93.

Title: Kim YH, et al. 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose increases a population of T regulatory cells and inhibits IgE production in ovalbumin-sensitized mice. Int Immunopharmacol. 2015 May;26(1):30-6.

Title: Ahn D, et al. The Longevity Properties of 1,2,3,4,6-Penta-O-Galloyl-β-D-Glucose from Curcuma longa in Caenorhabditis elegans. Biomol Ther (Seoul). 2013 Nov;21(6):442-6.

Title: Tu Z, et al. Pentagalloylglucose Inhibits the Replication of Rabies Virus via Mediation of the miR-455/SOCS3/STAT3/IL-6 Pathway. J Virol. 2019 Aug 28;93(18). pii: e00539-19.

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SDS
Tags:14937-32-7 Molecular Formula|14937-32-7 MDL|14937-32-7 SMILES|14937-32-7 1,2,3,4,6-Penta-O-galloyl-beta-D-glucopyranose