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(-)-Epigallocatechin

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-E1001

  • Specification : 98%

  • CAS number : 970-74-1

  • Formula : C15H14O7

  • Molecular Weight : 306.27

  • PUBCHEM ID : 72277

  • Volume : 20mg

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Catalogue Number

BF-E1001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

306.27

Appearance

White crystalline powder

Botanical Source

Vitis vinifera,Tripterygium wilfordii,Apocynum venetum,Acacia catechu,Camellia sinensis

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)O

Synonyms

EGC/Galloepicatechin/epigallocatechol/Sunphenon EGC/(-)-Epigallo catechin/(-)-Epigallocatechin/(−)-Epigallocatechin/(-)-Epigallocatechin (EGC)/(2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,5,7-chromanetriol/Teacatechin II/EPIGALLOCATECHIN/(2R,3R)-2-(3,4,5-Trihydroxyphenyl)chromane-3,5,7-triol/Greenteacatechins/(-)-EGC:2H-1-Benzopyran-3,5,7-triol,3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-, (2R-cis)-,/2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-, (2R,3R)-/epi

IUPAC Name

(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol

Applications

(-)-Epigallocatechin is the most abundant flavonoid in green tea, can bind to unfolded native polypeptides and prevent conversion to amyloid fibrils.IC50 value:Target: in vitro: EGCG is a potent inhibitor of amyloidogenic cystatin I66Q amyloid fibril formation in vitro. Computational analysis suggests that EGCG prevents amyloidogenic cystatin fibril formation by stabilizing the molecule in its native-like state as opposed to redirecting aggregation to disordered, amorphous aggregates [1]. Combined curcumin and EGCG treatment reduced the cancer stem-like Cluster of differentiation 44 (CD44)-positive cell population. Western blot and immunoprecipitation analyses revealed that curcumin and EGCG specifically inhibited STAT3 phosphorylation and STAT3-NFkB interaction was retained [2]. EGCG exhibited a MIC and MBC of 5μg/mL and 20μg/mL respectively and effectively eradicated E. faecalis biofilms. EGCG induced the formation of hydroxyl radicals in E. faecalis. The addition of DIP protected E. faecalis against EGCG-mediated antibacterial effects. At sub-MIC, EGCG induced significant down-regulation of E. faecalis virulence genes [3].

Density

1.7±0.1 g/cm3

Solubility

Methanol

Flash Point

368.5±31.5 °C

Boiling Point

685.6±55.0 °C at 760 mmHg

Melting Point

208-210°C

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:970-74-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31756664

Abstract

“Structural investigations, based on density functional theory (DFT) calculations, are performed on tea catechins, including 4-aminobutyric acid (GABA), L-theanine (Thea), caffeine (CAF), theobromine (TB), theophylline (TP), catechin (C), epicatechin (EC), gallocatechin (GC), epigallocatechin (EGC), catechin gallate (CG), epicatechin gallate (ECG), gallocatechin gallate (GCG) and epigallocatechin gallate (EGCG). With an identified lowest energy conformer of investigated molecules, FTIR and FT-Raman spectra have been assigned according to DFT calculations in the way of B3LYP/6-31 + G (d, p). Normal spectra of these catechin powders are also measured by Raman spectrometers. There is a kind of everlasting correlation between experimental results and theoretical data. And our research has also obtained a clear evidence for reliable assignments of vibrational bands, bringing great feasibility to the rapid tea catechin detection.
Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

Density functional theory; FT-IR; Raman spectra; Tea catechins

Title

Vibrational (FT-IR, Raman) analysis of tea catechins based on both theoretical calculations and experiments.

Author

Xia J1, Wang D2, Liang P3, Zhang4, Du X5, Ni D4, Yu Z6.

Publish date

2020 Jan

PMID

31613618

Abstract

In this study, derivatization of epigallocatechin (EGC) by representative phytosterols (stigmasterol and β-sitosterol) was performed employing Steglich esterification. The structural identity and purity of epigallocatechin β-sitosterol (ESi) and epigallocatechin stigmasterol (ESt) were confirmed by NMR, FT-IR, and HPLC-MS. Further evaluation of ESi and ESt revealed their extraordinary antioxidant activities in O/W emulsion. Two different radical sources in oil or aqueous phase were applied to explore the antioxidant behavior in O/W emulsion. The mechanism was further investigated by fluorescent microscopy and transmission electron microscopy (TEM). Furthermore, incorporation of EGC with stigmasterol and β-sitosterol notably enhanced the cholesterol-reducing activity. TEM studies suggested the hydrogen bonding of EGC strengthened the aggregation network of ESi and ESt in the bile salt micelle. The exceptional properties of ESi and ESt signified their intriguing utilization in the food industry.

KEYWORDS

O/W emulsion; Steglich esterification; antioxidant activity; cholesterol-reducing activity; epigallocatechin; phytosterol

Title

Enhancement of Antioxidant Activity in O/W Emulsion and Cholesterol-Reducing Capacity of Epigallocatechin by Derivatization with Representative Phytosterols.

Author

Wang S1, Fan J1, Xu L1, Ye K1, Shu T2, Liu S1,2.

Publish date

2019 Nov 13

PMID

31532890

Abstract

“Catechins in green tea are well-known to be effective in reducing the risk of obesity. The purpose of this study was to elucidate the effects of catechins present in green tea on adipocyte differentiation and mature adipocyte metabolism. Treatment of 3T3-L1 mouse adipocyte during differentiation adipocytes with (-)-epigallocatechin (EGC) and gallic acid (GA) resulted in dose-dependent inhibition of adipogenesis. Specifically, EGC increased adiponectin and uncoupling protein 1 (UCP1) transcription in mature adipocytes. Transcription levels of adipose triglyceride lipase (ATGL) and hormone-sensitive lipase (HSL) were not significantly impacted by either of the compounds. These results suggest that the EGC is the most effective catechin having anti-obesity activity. Finally, EGC is an attractive candidate component for remodeling obesity.

© 2019 Wiley-VHCA AG, Zurich, Switzerland.”

KEYWORDS

(−)-epigallocatechin; (−)-epigallocatechin gallate; anti-obesity; gallic acid

Title

Epigallocatechin Exerts Anti-Obesity Effect in Brown Adipose Tissue.

Author

Kim HS1, Moon JH1, Kim YM1, Huh JY2.

Publish date

2019 Oct