E3768
(−)-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:
Molecular Weight:
306.27
NACRES:
NA.21
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:
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
SMILES string
O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3cc(O)c(O)c(O)c3
InChI key
XMOCLSLCDHWDHP-IUODEOHRSA-N
biological source
green tea
assay
≥95% (HPLC)
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
2-8°C
Quality Level
Gene Information
human ... CYP1A2(1544)
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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.
General description
(−)-Epigallocatechin is one of the main catechin compounds found in green tea and the most abundant one (~20%), with antioxidant properties.
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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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)
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
Tugba Kose et al.
Pharmaceuticals (Basel, Switzerland), 12(1) (2019-02-10)
Ferroptosis is a form of programmed cell death that is characterized by lipid peroxidation and is inducible by iron and the accumulation of reactive oxygen species (ROS). It is triggered by erastin but inhibited by antioxidants such as -tocopherol, -carotene
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
Li-Ping Bai et al.
PloS one, 8(1), e53962-e53962 (2013-01-22)
With the aim of enhancing G-quadruplex binding activity, two new glucosaminosides (16, 18) of penta-methylated epigallocatechin were synthesized by chemical glycosylation. Subsequent ESI-TOF-MS analysis demonstrated that these two glucosaminoside derivatives exhibit much stronger binding activity to human telomeric DNA and
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