Penta-O-galloyl-β-D-glucose hydrate

SIGMA/G7548 - ≥96% (HPLC)

Synonym: 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

CAS Number: 14937-32-7 (anhydrous)
Empirical Formula (Hill Notation): C₄₁H₃₂O₂₆ · xH₂O
Molecular Weight: 940.68 (anhydrous basis)
MDL Number: MFCD18632553
Linear Formula: C₄₁H₃₂O₂₆ · xH₂O
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-G7548-5MG	5 mg	$122.00 1/EA	Add To Favorites
45-G7548-25MG	25 mg	$265.00 1/EA	Add To Favorites

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This image depicts G7548-5MG.

Properties
Descriptions
Safety Info.
Basic Data

assay	≥96% (HPLC)
color	light brown
form	powder
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
optical activity	[α]/D +14 to +26°, c = 0.2 in acetone-d₆
Quality Level	100
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
solubility	DMSO: ≥20 mg/mL
storage temp.	2-8°C

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:	Autophagy inducer in human PC-3 and mouse TRAMP-C2 prostate cancer cells
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.
Biochem/physiol Actions:	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 .
Packaging:	5, 25 mg in glass bottle

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥96% (HPLC)
Storage Temp.	2-8°C
UNSPSC	12352200

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