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G7548

Sigma-Aldrich

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

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25 MG
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About This Item

Empirical Formula (Hill Notation):
C41H32O26 · xH2O
CAS Number:
Molecular Weight:
940.68 (anhydrous basis)
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

$108.30

List Price$114.00Save 5%
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In StockDetails


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Quality Level

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

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1 of 4

This Item
28594313403186730
form

powder

form

powder

form

powder

form

solid

assay

≥96% (HPLC)

assay

98%

assay

98%

assay

≥98.0% (TLC)

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

−20°C

solubility

DMSO: ≥20 mg/mL

solubility

-

solubility

-

solubility

-

color

light brown

color

-

color

-

color

-

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Questions

1–2 of 2 Questions  
  1. Is this sterile for cell culture use or does it require additional filtering?

    1 answer
    1. This product has not been sterilized. For cell culture applications, filter sterilization of the reconstituted solution is needed.

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  2. Where is pentagalloylglucose obtained from?

    1 answer
    1. The source of this product may vary from lot to lot. This information is available on the lot-specific Certificate of Origin.

      Please see the link below to access a specific lot or to request a sample Certificate:
      https://www.sigmaaldrich.com/documents-search?tab=coo

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