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E3768

(−)-Epigallocatechin

Name: (−)-Epigallocatechin
Brand: SIAL

≥95% (HPLC), from green tea

Synonym(s):

(−)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol, (−)-cis-3,3′,4′,5,5′,7-Hexahydroxyflavane

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₄O₇

CAS Number:

970-74-1

Molecular Weight:

306.27

NACRES:

NA.21

PubChem Substance ID:

24894529

UNSPSC Code:

12352205

MDL number:

MFCD00075939

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biological source

green tea

Quality Level

200

assay

≥95% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3cc(O)c(O)c(O)c3

InChI

1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1

InChI key

XMOCLSLCDHWDHP-IUODEOHRSA-N

Gene Information

human ... CYP1A2(1544)

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Biochemicals

Natural Products for Research and Discovery

General description

(−)-Epigallocatechin is one of the main catechin compounds found in green tea and the most abundant one (~20%), with antioxidant properties.

Application

(−)-Epigallocatechin (EGC) has been used:

as a reference standard in high-performance liquid chromatography (HPLC) analysis
to analyze its inhibitory effect on α-amylase and α-glucosidase activity to control postprandial hyperglycemia in Diabetes mellitus
in cell viability assays to check its efficacy and protection against ferroptosis and iron toxicity in murine pancreatic β-cells
to evaluate its potential anti-inflammatory effects on long-term acute and chronic Pristen-induced arthritis
to treat pregnant and nursing mice, on in vitro angiogenesis, proliferation, and movement of endothelial cells
to evaluate its effect on pregnant and nursing mice spleen based on the number and localization of CD4⁺ (cluster of differentiation 4) and CD8⁺ cluster of differentiation 8) cells

Biochem/physiol Actions

(−)-Epigallocatechin (EGC) has proven to be an anti-cancer agent by its inhibitory effects on heregulin-b1 (HRG)-induced migration/invasion in MCF-7 human breast carcinoma cells. It has also shown strong antiviral activity against the herpes simplex virus.

Green tea polyphenol. Anticancer agent. Lower antioxidant activity than EGCG.

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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Certificates of Analysis (COA)

Lot/Batch Number

0000548542

0000523156

0000523158

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Inhibitory effect of (-)-epigallocatechin and (-)-epigallocatechin gallate against heregulin beta1-induced migration/invasion of the MCF-7 breast carcinoma cell line.

Yukihiro Kushima et al.

Biological & pharmaceutical bulletin, 32(5), 899-904 (2009-05-08)

Migration/invasion is involved in the multiple steps of metastasis, resulting in a poor prognosis of breast cancer. (-)-Epigallocatechin-3-gallate (EGCG) in green tea inhibits the metastasis of some cancer cell lines. Cell migration/invasion assays using Boyden chambers demonstrated that (-)-epigallocatechin (EGC)

The effect of feeding mice during gestation and nursing with Rhodiola kirilowii extracts or epigallocatechin on CD4 and CD8 cells number and distribution in the spleen of their progeny.

Sławomir Lewicki et al.

Central-European journal of immunology, 42(1), 10-16 (2017-07-07)

Rhodiola kirilowii, a member of Crassulaceae family, grows wildly in Asiatic mountains and is also cultivated in some European countries. Its underground parts traditionally are used for enhance physical and mental performance of the body. In our previous papers we

Long-Term Effects of (-)-Epigallocatechin Gallate (EGCG) on Pristane-Induced Arthritis (PIA) in Female Dark Agouti Rats.

Anna Leichsenring et al.

PloS one, 11(3), e0152518-e0152518 (2016-03-31)

Rheumatoid arthritis (RA)--a widespread chronic inflammatory disease in industrialized countries--is characterized by a persistent and progressive joint destruction. The chronic pro-inflammatory state results from a mutual activation of the innate and the adaptive immune system, while the exact pathogenesis mechanism

Evaluation of alpha-amylase and alpha-glucosidase inhibitory activity of flavonoids

Gu C, et al.,

International Journal of Food and Nutrition Science, 2(6), 1-6 (2015)

Different effects of feeding pregnant and lactating mice Rhodiola kirilowii aqueous and hydro-alcoholic extracts on their serum angiogenic activity and content of selected polyphenols.

Robert Zdanowski et al.

Central-European journal of immunology, 42(1), 17-23 (2017-07-07)

Angiogenesis plays an important role in many physiological processes, among them the formation of tissues and organs during embryogenesis. A lot of medicinal plants exhibit angiomodulatory properties. This creates the need for a thorough check of whether the plant extracts

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Articles

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
E3768-5MG	04061835512485

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