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G7548

Penta-O-galloyl-β-D-glucose hydrate

Name: Penta-O-galloyl-&#946;-D-glucose hydrate
Brand: SIGMA

≥96% (HPLC), apoptosis inducer, powder

Synonym(s):

1,2,3,4,6-Penta-O-galloyl-b-D-glucopyranose, 1,2,3,4,6-pentakis(3,4,5-trihydroxybenzoate)-b-D-Glucopyranose, Gallic acid, pentaester with b-D-glucopyranose, Glucopyranose, pentagallate, b-D, PGG, Penta-1,2,3,4,6-O-galloyl-b-D-glucose, Penta-O-galloyl-beta-D-glucose

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About This Item

Empirical Formula (Hill Notation):

C₄₁H₃₂O₂₆ · xH₂O

CAS Number:

14937-32-7

Molecular Weight:

940.68 (anhydrous basis)

UNSPSC Code:

12352200

PubChem Substance ID:

329799964

NACRES:

NA.77

MDL number:

MFCD18632553

Assay:

≥96% (HPLC)

Form:

powder

Quality level:

100

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Product Name

Penta-O-galloyl-β-D-glucose hydrate, ≥96% (HPLC)

Quality Level

100

assay

≥96% (HPLC)

form

powder

optical activity

[α]/D +14 to +26°, c = 0.2 in acetone-d₆

color

light brown

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

O=C(O[C@H]([C@H]([C@@H]([C@@H](COC(C1=CC(O)=C(O)C(O)=C1)=O)O2)OC(C3=CC(O)=C(O)C(O)=C3)=O)OC(C4=CC(O)=C(O)C(O)=C4)=O)[C@@H]2OC(C5=CC(O)=C(O)C(O)=C5)=O)C6=CC(O)=C(O)C(O)=C6.O

InChI

1S/C41H32O26.H2O/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16;/h1-10,27,33-35,41-56H,11H2;1H2/t27-,33-,34+,35-,41+;/m1./s1

InChI key

JCJIMLXECAATFH-ZSJSDXHXSA-N

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

Penta-O-galloyl-β-D-glucose hydrate (PCG) has been used as an inhibitor of abdominal aortic aneurysms (AAA) and matrix metalloproteinase (MMP) related metastatic activity.

Biochem/physiol Actions

Penta-O-galloyl-β-D-glucose hydrate (PCG) is a polyphenolic gallotannin compound produced by plants. It has an ability to inhibit matrix metalloproteinase (MMP) related metastatic activity. Thus, PCG can be used for treating metastatic activity in squamous cell carcinoma. In addition, it also acts as a potential drug for stabilizing small abdominal aneurysms.

Autophagy inducer in human PC-3 and mouse TRAMP-C2 prostate cancer cells

PGG induces predominantly (caspase dependent) apoptosis in DU145 and LNCaP cells, while inducing autophagy in more resistant PC3 and TRAMP-C2 cells. It appears that PGG targeted signaling downstream of rather than the mTOR itself. Polyphenolic pyranoses were reported (J Biol Chem. 2010, 285 (11), 7892-902) to inhibit the plasminogen activator inhibitor type 1 (PAI-1).

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

涉药品监管产品

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Certificates of Analysis (COA)

Lot/Batch Number

0000506115

0000432700

0000399139

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

Hyo-Jung Lee et al.

Kidney international, 79(5), 538-545 (2010-11-19)

Adhesion of calcium oxalate (CaOx) crystals to kidney cells may be a key event in the pathogenesis of kidney stones associated with marked hyperoxaluria. Previously, we found that 1,2,3,4,6-penta-O-galloyl-β-D-glucose (PGG), isolated from a traditional medicinal herb, reduced CaOx crystal adhesion

Small molecule inhibition of matrix metalloproteinases as a potential therapeutic for metastatic activity in squamous cell carcinoma

Matias C, et al.

Oral cancer, 3(1-2), 1-8 (2019)

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.

Anna K Kiss et al.

Journal of agricultural and food chemistry, 58(18), 9960-9966 (2010-08-21)

In this study, we analyzed ex vivo the effect of an aqueous extract of Oenothera paradoxa defatted seeds on the formation of neutrophil-derived oxidants. For defining active compounds, we also tested lypophilic extract constituents such as gallic acid, (+)-catechin, ellagic

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.

Hsiu-Chen Huang et al.

Journal of agricultural and food chemistry, 59(12), 6765-6775 (2011-05-24)

The F-box protein S-phase kinase-associated protein 2 (Skp2), which acts as an oncogene through targeting p27 for degradation, is overexpressed in many different human cancers. Skp2 can play an important role in breast cancer progression and may also be a

Inhibitory effects of 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose on biofilm formation by Staphylococcus aureus.

Mei-Hui Lin et al.

Antimicrobial agents and chemotherapy, 55(3), 1021-1027 (2010-12-22)

1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose (PGG) is an active ingredient in plants that are commonly used in Chinese medicine to treat inflammation. We demonstrate here that PGG, at 6.25 μM, does not inhibit the growth of Staphylococcus aureus, and yet it prevents biofilm formation

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Global Trade Item Number

SKU	GTIN
G7548-25MG	04061833642948
G7548-5MG	04061833642955

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