G7548

Penta-O-galloyl-β-D-glucose hydrate

≥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
• 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

Properties

• Product Name: Penta-O-galloyl-β-D-glucose hydrate, ≥96% (HPLC)
• 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

Description

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

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).

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.

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable