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E3768

Sigma-Aldrich

(−)-Epigallocatechin

≥95% (HPLC), from green tea

Sinonimo/i:

(−)-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

Formula empirica (notazione di Hill):
C15H14O7
Numero CAS:
970-74-1
Peso molecolare:
306.27
Numero MDL:
MFCD00075939
Codice UNSPSC:
12352205
ID PubChem:
24894529
NACRES:
NA.21

Origine biologica

green tea

Livello qualitativo

200

Saggio

≥95% (HPLC)

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Temperatura di conservazione

2-8°C

Stringa SMILE

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
XMOCLSLCDHWDHP-IUODEOHRSA-N

Informazioni sul gene

human ... CYP1A2(1544)

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Descrizione generale

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

Applicazioni

(−)-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

Azioni biochim/fisiol

(−)-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.

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
SLCL5281
SLCG2781
SLCB1171
SLBW7003
SLBR6704V

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(−)-Catechin gallate ≥98% (HPLC), from green tea

Sigma-Aldrich

C0692

(−)-Catechin gallate

(−)-Epigallocatechin gallate analytical standard

Supelco

93894

(−)-Epigallocatechin gallate

Epicatechin gallate primary reference standard

03950590

Epicatechin gallate

Epigallocatechin gallate primary reference standard

03970590

Epigallocatechin gallate

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

Sigma-Aldrich

C0567

(−)-Catechin

(±)-Epigallocatechin-2,3,4-13C3 ≥99 atom % 13C, ≥97% (CP)

Sigma-Aldrich

900369

(±)-Epigallocatechin-2,3,4-13C3

(−)-Gallocatechin analytical standard

Supelco

01388

(−)-Gallocatechin

(−)-Gallocatechin gallate analytical standard

Supelco

80352

(−)-Gallocatechin gallate

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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Articoli

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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