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E4143

Sigma-Aldrich

(−)-Epigallocatechin gallate

≥95%

Sinônimo(s):

(−)-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

Fórmula empírica (Notação de Hill):
C22H18O11
Número CAS:
989-51-5
Peso molecular:
458.37
Número MDL:
MFCD00075940
Código UNSPSC:
12352205
ID de substância PubChem:
57654158
NACRES:
NA.25

Nível de qualidade

200

Ensaio

≥95%

solubilidade

H2O: ≥5 mg/mL, clear

aplicação(ões)

metabolomics
vitamins, nutraceuticals, and natural products

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

chave InChI

WMBWREPUVVBILR-WIYYLYMNSA-N

Informações sobre genes

human ... CYP1A2(1544)

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Descrição geral

(−)-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.

Aplicação

(-)-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

Ações bioquímicas/fisiológicas

(-)-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.

Pictogramas

Exclamation markEnvironment
GHS07,GHS09

Palavra indicadora

Warning

Frases de perigo

H302,H317,H319,H411

Classificações de perigo

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

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

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Certificados de análise (COA)

Lot/Batch Number
SLCK1721
SLCF9196
SLBZ2865
SLBQ4582V
SLBV1254

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(−)-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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