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E4143

Sigma-Aldrich

(-)-表没食子儿茶素没食子酸酯

≥95%

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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
经验公式（希尔记法）:
C22H18O11
CAS号:
989-51-5
分子量:
458.37
MDL编号:
MFCD00075940
PubChem化学物质编号:
57654158

质量水平

200

检测方案

≥95%

溶解性

H2O: ≥5 mg/mL, clear

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

储存温度

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

一般描述

(−)-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。

应用

(-)-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

生化/生理作用

(-)-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。

象形图

Exclamation markEnvironment
GHS07,GHS09

警示用语：

Warning

危险分类

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

储存分类代码

11 - Combustible Solids

WGK

WGK 2

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

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  1. How does the storage temperature relate to shipping conditions?

    The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.

  2. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  3. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  5. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  6. Is (-)-Epigallocatechin gallate (Product No. E4143) sterile and tested for endotoxins?

    Product No. E4143 ((-)-Epigallocatechin gallate) is not prepared under sterile conditions and has not been tested for endotoxins.

  7. Is (-)-Epigallocatechin gallate (Product No. E4143) for human use

    No. Product No. E4143 ((-)-Epigallocatechin gallate) is for laboratory research use only, not for human use.

  8. What is the solubility of (-)-Epigallocatechin gallate (E4143)?

    We have tested the solubility of (-)-Epigallocatechin gallate at 5 mg/mL in water.

  9. What is the solution stability of (-)-Epigallocatechin gallate (E4143)?

    A solution of (-)-Epigallocatechin gallate in water at a concentration of 0.3 mg/mL was found to have significantly decreased in purity (from 99.6% to 81.7%) after 2.5 hours at room temperature. A similar solution of (-)-Epigallocatechin gallate in water at a concentration of 0.3 mg/mL was found to have decreased in purity only slightly (from 99.5% to 99.3%) after 2.0 hours at 4°C.

  10. Can (-)-Epigallocatechin gallate be determined in plasma and urine?

    The determination of (-)-Epigallocatechin gallate in plasma and urine by HPLC has been reported in Cancer Epidemiol. Biomark. Prev., 4, 393 (1995).

  11. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
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)
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)
(-)-Epigallocatechin-3-gallate stimulates myogenic differentiation through TAZ activation
Kim AR, et al.
Biochemical and Biophysical Research Communications, 486(2), 378-384 (2017)
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