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
| 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 |
