G7548

Penta-O-galloyl-β-D-glucose hydrate

≥96% (HPLC)

• Synonyme(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
• Formule empirique (notation de Hill) : C₄₁H₃₂O₂₆ · xH₂O
• Numéro CAS: 14937-32-7
• Poids moléculaire : 940.68 (anhydrous basis)
• Numéro MDL: MFCD18632553
• Code UNSPSC : 12352200
• ID de substance PubChem : 329799964
• Nomenclature NACRES : NA.77

Propriétés

• Niveau de qualité: 100
• Essai: ≥96% (HPLC)
• Forme: powder
• Activité optique: [α]/D +14 to +26°, c = 0.2 in acetone-d₆
• Couleur: light brown
• Solubilité: DMSO: ≥20 mg/mL
• Température de stockage: 2-8°C
• Chaîne SMILES: 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
• Clé InChI: 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]

Actions biochimiques/physiologiques

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]

Caractéristiques et avantages

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Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable