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E4143

Sigma-Aldrich

(−)-Epigallocatechin gallate

≥95%

Sinonimo/i:

(−)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate, (−)-cis-3,3′,4′,5,5′,7-Hexahydroxy-flavane-3-gallate, EGCG

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About This Item

Formula empirica (notazione di Hill):
C22H18O11
Numero CAS:
989-51-5
Peso molecolare:
458.37
Numero MDL:
MFCD00075940
Codice UNSPSC:
12352205
ID PubChem:
57654158
NACRES:
NA.25

Saggio

≥95%

Solubilità

H2O: ≥5 mg/mL, clear

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)c4cc(O)c(O)c(O)c4

InChI

1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
WMBWREPUVVBILR-WIYYLYMNSA-N

Informazioni sul gene

human ... CYP1A2(1544)

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Descrizione generale

(−)-Epigallocatechin gallate from green tea is the prime bioactive component, accounting for 50-80% of the total catechin content. It comprises a chemical structure similar to that of epicatechin gallate (ECG), an ester of gallic acid and epigallocatechin.

Applicazioni

(-)-Epigallocatechin gallate has been used:
  • as an anti-tumor agent on murine TRAMP metastatic prostate cell line by cell proliferation assay, apoptosis detection and modified Boyden-chamber assay
  • induces cell death in acute myeloid leukaemia through death associated protein kinase-2 pathway analyzed through cell viability, cell cycle and apoptosis assay
  • as an inhibitor of osteoclast differentiation in murine preosteoclast cell line RAW264.7
  • to promote myogenic differentiation

Azioni biochim/fisiol

(-)-Epigallocatechin gallate (EGCG), an antioxidant polyphenol flavonoid exerts anti-tumor properties by inhibiting telomerase and DNA methyltransferase activity. EGCG inhibits the expression of matrix metalloproteinase-2 (MMP-2), MMP-9 and reduces the invasiveness. EGCG blocks the activation of epidermal growth factor (EGF) receptors and human epidermal growth factor receptor-2 (HER-2). EGCG increases bone mineral density and reduces bone resorption. EGCG inhibits osteoclastogenesis by inhibiting receptor activator of nuclear factor κ-B ligand (RANKL) induced nuclear factor κ B (NF-κB) transcriptional activity. EGCG reduces skeletal muscle atrophy. EGCG has anti-aging property and increases myogenic differentiation. EGCG inhibits fatty acid synthase and glutamate dehydrogenase activity.

Pittogrammi

Exclamation markEnvironment
GHS07,GHS09

Avvertenze

Warning

Indicazioni di pericolo

H302,H317,H319,H411

Classi di pericolo

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 2

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
SLCK1721
SLCF9196
SLBZ2865
SLBQ4582V
SLBV1254

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

Sigma-Aldrich

G6782

(−)-Gallocatechin gallate

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

Sigma-Aldrich

E4018

(−)-Epicatechin

(−)-Epigallocatechin analytical standard

Supelco

08108

(−)-Epigallocatechin

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

Sigma-Aldrich

C0692

(−)-Catechin gallate

(−)-Epicatechin ≥90% (HPLC)

Sigma-Aldrich

E1753

(−)-Epicatechin

Epicatechin gallate primary reference standard

03950590

Epicatechin gallate

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

Sigma-Aldrich

900376

(±)-Epigallocatechin-2,3,4-13C3 gallate

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

Sigma-Aldrich

C1251

(+)-Catechin hydrate

(-)-Epigallocatechin-3-gallate stimulates myogenic differentiation through TAZ activation
Kim AR, et al.
Biochemical and Biophysical Research Communications, 486(2), 378-384 (2017)
(-)-Epigallocatechin gallate inhibition of osteoclastic differentiation via NF-kappaB
Lin RW, et al.
Biochemical and Biophysical Research Communications, 379(4), 1033-1037 (2009)
Proposed mechanisms of (-)-epigallocatechin-3-gallate for anti-obesity
Moon HS, et al.
Chemico-Biological Interactions, 167(2), 85-98 (2007)
Prostate carcinoma and green tea:(-) epigallocatechin-3-gallate inhibits inflammation-triggered MMP-2 activation and invasion in murine TRAMP model
Sartor L, et al.
International Journal of Cancer. Journal International Du Cancer, 112(5), 823-829 (2004)
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
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