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E3768

Sigma-Aldrich

(−)-Epigallocatechin

≥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
MDL number:
MFCD00075939
UNSPSC Code:
12352205
PubChem Substance ID:
24894529
NACRES:
NA.21

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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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000396689
0000385040
0000385040
0000346713
0000299444

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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
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)
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)
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
Jun Xu et al.
Molecules (Basel, Switzerland), 22(8) (2017-08-15)
Over the centuries, infectious diseases caused by viruses have seriously threatened human health globally. Viruses are responsible not only for acute infections but also many chronic infectious diseases. To prevent diseases caused by viruses, the discovery of effective antiviral drugs
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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.

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