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Merck

E3893

(−)-Epicatechin gallate

≥98% (HPLC), from green tea

Synonyme(s) :

(−)-cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate, (−)-cis-3,3′,4′,5,7-Pentahydroxyflavane 3-gallate, 3-O-Galloylepicatechin

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About This Item

Formule empirique (notation de Hill) :
C22H18O10
Numéro CAS:
1257-08-5
Poids moléculaire :
442.37
NACRES:
NA.21
PubChem Substance ID:
24894531
UNSPSC Code:
12352205
MDL number:
MFCD00075936

Nom du produit

(−)-Epicatechin gallate, ≥98% (HPLC), from green tea

InChI

1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1

SMILES string

Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4ccc(O)c(O)c4

InChI key

LSHVYAFMTMFKBA-TZIWHRDSSA-N

biological source

green tea

assay

≥98% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... CYP1A2(1544)

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Catégories apparentées

Application

(−)-Epicatechin gallate has been used:
  • in cell proliferation assays on the human brain microvascular endothelial cells (HBMVECs) to understand its effectiveness against anti-ischemic/reperfusion injury
  • as an inhibitor in Human Salivary α-Amylase (HAS) and α-Glucosidase (AGH) in inhibition assays
  • may be used as a cancer chemopreventive polyphenol in two human colorectal cell lines HCT-116 and SW-480
  • as an inhibitor to in vitro collagenase and elastase enzymes
  • as a supplement in spermatozoa incubation to check its effectiveness against oxidative stress

Biochem/physiol Actions

(−)-Epicatechin gallate (ECG), a potent free-radical scavenger has an inhibitory effect on collagenase and elastase enzymes making it an anti-aging agent. It displays antiproliferative effects on human colorectal cells and hence is a chemo-preventative agent. It influences cell survival, preventing apoptosis or autophagy by promoting cell proliferation in oxygen-glucose deprived human brain microvascular endothelial cells. Being structurally and functionally similar to EGCG, ECG might be involved in balancing the mammalian target of rapamycin (mTOR)-AMP-activated protein kinase (AMPK) pathways in endoplasmic reticulum stress. It prevents cell death in this scenario by showing resistance against oxygen-deprived cells. ECG may contribute in preventing oxidative stress. It effectively inhibits secretory sphingomyelinase in many disease states and provides protection for human spermatozoa in Assisted reproductive technology (ART).

General description

(−)-Epicatechin gallate is one of the major polyphenols present in green tea. It belongs to the catechin gallates group of organic compounds. ECG has a chemical structure like that of (−)-epigallocatechin gallate (EGCG), the other major polyphenol found in green tea.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
WXBF7565V
WXBF5281V
WXBD8804V
WXBD9038V
WXBD6835V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Lee Wah Koh et al.
Journal of agricultural and food chemistry, 58(1), 148-154 (2010-01-07)
Current work investigated the ability of different tea (green, oolong and black teas) in inhibiting human salivary alpha-amylase (HSA) and mammalian alpha-glucosidase (AGH). The inhibitory profiles were correlated to their major polyphenol content (theaflavins and catechins). The fully fermented black
Marianna Holczer et al.
Oxidative medicine and cellular longevity, 2018, 6721530-6721530 (2018-04-11)
The maintenance of cellular homeostasis is largely dependent on the ability of cells to give an adequate response to various internal and external stimuli. We have recently proposed that the life-and-death decision in endoplasmic reticulum (ER) stress response is defined
Keiko Kobayashi et al.
Journal of nutritional science and vitaminology, 62(2), 123-129 (2016-06-07)
Sphingomyelinases (SMases) are key enzymes involved in many diseases which are caused by oxidative stress, such as atherosclerosis, diabetes mellitus, nonalcoholic fatty liver disease, and Alzheimer's disease. SMases hydrolyze sphingomyelin to generate ceramide, a well-known pro-apoptotic lipid. SMases are classified
Wanda C Reygaert
BioMed research international, 2018, 9105261-9105261 (2018-08-15)
Green tea is one of the most popular drinks consumed worldwide. Produced mainly in Asian countries from the leaves of the Camellia sinensis plant, the potential health benefits have been widely studied. Recently, researchers have studied the ability of green
Guang-Jian Du et al.
Nutrients, 4(11), 1679-1691 (2012-12-04)
Green tea is a popular drink consumed daily by millions of people around the world. Previous studies have shown that some polyphenol compounds from green tea possess anticancer activities. However, systemic evaluation was limited. In this study, we determined the
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