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E3893

Sigma-Aldrich

(−)-Epicatechin gallate

≥98% (HPLC), from green tea

Sinonimo/i:

(−)-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

Formula empirica (notazione di Hill):
C22H18O10
Numero CAS:
1257-08-5
Peso molecolare:
442.37
Numero MDL:
MFCD00075936
Codice UNSPSC:
12352205
ID PubChem:
24894531
NACRES:
NA.21

Origine biologica

green tea

Saggio

≥98% (HPLC)

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Temperatura di conservazione

2-8°C

Stringa SMILE

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
LSHVYAFMTMFKBA-TZIWHRDSSA-N

Informazioni sul gene

human ... CYP1A2(1544)

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Categorie correlate

Descrizione generale

(−)-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.

Applicazioni

(−)-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

Azioni biochim/fisiol

(−)-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).

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
WXBD8804V
WXBD9038V
WXBD6835V
WXBD3508V
WXBD0502V

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Sigma-Aldrich

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Supelco

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(−)-Epicatechin analytical standard

Supelco

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(−)-Epicatechin

(−)-Epigallocatechin gallate ≥80% (HPLC), from green tea

Sigma-Aldrich

E4268

(−)-Epigallocatechin gallate

(−)-Catechin ≥97% (HPLC), from green tea

Sigma-Aldrich

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(−)-Catechin

(−)-Gallocatechin gallate analytical standard

Supelco

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Epicatechin primary reference standard

03940590

Epicatechin

(+)-Catechin hydrate ≥98% (HPLC), powder

Sigma-Aldrich

C1251

(+)-Catechin hydrate

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
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
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
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
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
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