G7548

Penta-O-galloyl-β-D-glucose hydrate

≥96% (HPLC)

• 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)
• MDL number: MFCD18632553
• UNSPSC Code: 12352200
• PubChem Substance ID: 329799964
• NACRES: NA.77

Properties

• 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

Description

Application

Penta-O-galloyl-β-D-glucose hydrate (PCG) has been used as an inhibitor of abdominal aortic aneurysms (AAA)[1] and matrix metalloproteinase (MMP) related metastatic activity.[2]

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.[2] 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.[2] In addition, it also acts as a potential drug for stabilizing small abdominal aneurysms.[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.

Safety Information

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