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G7548

Sigma-Aldrich

Penta-O-galloyl-β-D-glucose hydrate

≥96% (HPLC)

同義詞:

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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About This Item

經驗公式（希爾表示法）:
C41H32O26 · xH2O
CAS號碼:
14937-32-7
分子量：:
940.68 (anhydrous basis)
MDL號碼:
MFCD18632553
分類程式碼代碼:
12352200
PubChem物質ID:
329799964
NACRES:
NA.77
暫時無法取得訂價和供貨情況

品質等級

100

化驗

≥96% (HPLC)

形狀

powder

光學活性

[α]/D +14 to +26°, c = 0.2 in acetone-d6

顏色

light brown

溶解度

DMSO: ≥20 mg/mL

儲存溫度

2-8°C

SMILES 字串

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 密鑰

JCJIMLXECAATFH-ZSJSDXHXSA-N

應用

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]

生化／生理作用

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]

特點和優勢

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.

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

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分析證明 (COA)

Lot/Batch Number
0000329220
0000225376
0000225375
0000184148
0000192075

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Mei-Hui Lin et al.
Antimicrobial agents and chemotherapy, 55(3), 1021-1027 (2010-12-22)
1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose (PGG) is an active ingredient in plants that are commonly used in Chinese medicine to treat inflammation. We demonstrate here that PGG, at 6.25 μM, does not inhibit the growth of Staphylococcus aureus, and yet it prevents biofilm formation
Renate R Baumgartner et al.
Journal of natural products, 73(9), 1578-1581 (2010-09-02)
The inhibition of protein tyrosine phosphatase 1B (PTP1B) is of substantial interest for the treatment of type-2 diabetes mellitus. Using an in vitro enzyme assay with human recombinant PTP1B 1,2,3,4,6-penta-O-galloyl-D-glucopyranose was isolated from the roots of Paeonia lactiflora as an
Hyo-Jung Lee et al.
Kidney international, 79(5), 538-545 (2010-11-19)
Adhesion of calcium oxalate (CaOx) crystals to kidney cells may be a key event in the pathogenesis of kidney stones associated with marked hyperoxaluria. Previously, we found that 1,2,3,4,6-penta-O-galloyl-β-D-glucose (PGG), isolated from a traditional medicinal herb, reduced CaOx crystal adhesion
Small molecule inhibition of matrix metalloproteinases as a potential therapeutic for metastatic activity in squamous cell carcinoma
Matias C, et al.
Oral cancer, 3(1-2), 1-8 (2019)
Hsiu-Chen Huang et al.
Journal of agricultural and food chemistry, 59(12), 6765-6775 (2011-05-24)
The F-box protein S-phase kinase-associated protein 2 (Skp2), which acts as an oncogene through targeting p27 for degradation, is overexpressed in many different human cancers. Skp2 can play an important role in breast cancer progression and may also be a
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Questions

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  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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