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E4143

(-)-表没食子儿茶素没食子酸酯

≥95%

别名:

(-)-顺式-2-(3,4,5-三羟基苯基)-3,4-二氢-1(2H)-苯并吡喃-3,5,7--三醇 3-没食子酸酯, (-)-顺式-3,3′,4′,5,5′,7-六羟基-黄烷-3-没食子酸酯, EGCG

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关于此项目

经验公式（希尔记法）:
C22H18O11
化学文摘社编号:
989-51-5
分子量:
458.37
NACRES:
NA.25
PubChem Substance ID:
57654158
UNSPSC Code:
12352205
MDL number:
MFCD00075940
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Quality Level

200

assay

≥95%

solubility

H2O: ≥5 mg/mL, clear

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4cc(O)c(O)c(O)c4

InChI

1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1

InChI key

WMBWREPUVVBILR-WIYYLYMNSA-N

Gene Information

human ... CYP1A2(1544)

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相关类别

General description

(−)-表没食子儿茶素没食子酸酯（来源于绿茶）是绿茶中的主要生物活性成分，占儿茶素总含量的50-80%。它的化学结构类似于表儿茶素没食子酸酯(ECG)——没食子酸和表没食子儿茶素形成的酯类物质。

Application

(-)-表没食子儿茶素没食子酸酯已被用于：
  • 作为小鼠TRAMP转移性前列腺细胞系的抗肿瘤剂，用于细胞增殖试验、凋亡检测和改良型Boyden-chamber试验
  • 通过死亡相关蛋白激酶-2途径诱导急性髓细胞白血病细胞死亡，用于细胞活力、细胞周期和凋亡分析
  • 作为小鼠前破骨细胞系RAW264.7的破骨细胞分化的抑制剂
  • 促进成肌细胞分化

Biochem/physiol Actions

(-)-表没食子儿茶素没食子酸酯 (EGCG)是一种抗氧化多酚类黄酮化合物，它通过抑制端粒酶和DNA甲基转移酶活性而发挥抗肿瘤作用。EGCG可抑制基质金属蛋白酶-2（MMP-2）、MMP-9的表达并降低肿瘤的侵袭能力。EGCG可阻断表皮生长因子（EGF）受体和人表皮生长因子受体-2（HER-2）的活化。EGCG可增加骨矿物质密度并减少骨吸收。EGCG通过抑制核因子κ-B受体活化因子配体（RANKL）诱导的核因子 κ B(NF-κB)转录活性，进而抑制破骨细胞生成。EGCG可减少骨骼肌萎缩。EGCG具有抗衰老性，可增加成肌细胞分化。EGCG可抑制脂肪酸合成酶和谷氨酸脱氢酶活性。

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1

存储类别

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000544751
0000532560
0000532560
0000526509
0000526509

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Epigallocatechin-3-gallate induces cell death in acute myeloid leukaemia cells and supports all-trans retinoic acid-induced neutrophil differentiation via death-associated protein kinase 2
Britschgi A, et al.
British Journal of Haematology, 149(1), 55-64 (2010)
(-)-Epigallocatechin-3-gallate stimulates myogenic differentiation through TAZ activation
Kim AR, et al.
Biochemical and Biophysical Research Communications, 486(2), 378-384 (2017)
Takuya Miyagawa et al.
Pharmaceutics, 12(5) (2020-05-02)
Neovascularization (NV) of the cornea disrupts vision which leads to blindness. Investigation of antiangiogenic, slow-release and biocompatible approaches for treating corneal NV is of great importance. We designed an eye drop formulation containing gelatin/epigallocatechin-3-gallate (EGCG) nanoparticles (NPs) for targeted therapy
(-)-Epigallocatechin gallate inhibition of osteoclastic differentiation via NF-kappaB
Lin RW, et al.
Biochemical and Biophysical Research Communications, 379(4), 1033-1037 (2009)
Prostate carcinoma and green tea:(-) epigallocatechin-3-gallate inhibits inflammation-triggered MMP-2 activation and invasion in murine TRAMP model
Sartor L, et al.
International Journal of Cancer. Journal International Du Cancer, 112(5), 823-829 (2004)
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全球贸易项目编号

货号GTIN
E4143-50MG04061835544455

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