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E3893

(−)-Epicatechin gallate

Name: (−)-Epicatechin gallate
Brand: SIAL

≥98% (HPLC), from green tea

Synonym(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

Empirical Formula (Hill Notation):

C₂₂H₁₈O₁₀

CAS Number:

1257-08-5

Molecular Weight:

442.37

NACRES:

NA.21

PubChem Substance ID:

24894531

UNSPSC Code:

12352205

MDL number:

MFCD00075936

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biological source

green tea

Quality Level

100

assay

≥98% (HPLC)

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)c4ccc(O)c(O)c4

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

InChI key

LSHVYAFMTMFKBA-TZIWHRDSSA-N

Gene Information

human ... CYP1A2(1544)

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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.

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).

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Evaluation of different teas against starch digestibility by mammalian glycosidases.

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

Epicatechin Gallate Protects HBMVECs from Ischemia/Reperfusion Injury through Ameliorating Apoptosis and Autophagy and Promoting Neovascularization.

Bing Fu et al.

Oxidative medicine and cellular longevity, 2019, 7824684-7824684 (2019-04-10)

Green tea is one of the most beverages with antioxidants and nutrients. As one of the major components of green tea, (-)-epicatechin gallate (ECG) was evaluated for its antioxidative properties in the present study. Cell proliferation assay, tube formation, cell

Epigallocatechin-3-Gallate (EGCG) Promotes Autophagy-Dependent Survival via Influencing the Balance of mTOR-AMPK Pathways upon Endoplasmic Reticulum Stress.

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

Strong Inhibition of Secretory Sphingomyelinase by Catechins, Particularly by (-)-Epicatechin 3-O-Gallate and (-)-3'-O-Methylepigallocatechin 3-O-Gallate.

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

Green Tea Catechins: Their Use in Treating and Preventing Infectious Diseases.

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

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Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

膳食抗氧化剂

抗氧化剂可保护生物系统免受含氧自由基和氧化还原过渡金属离子（如铁、铜和镉）引起的氧化损伤。

Global Trade Item Number

SKU	GTIN
E3893-10MG	04061835544448

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