(-)-Epigallocatechin(EGC)

Names

[ CAS No. ]:
970-74-1

[ Name ]:
(-)-Epigallocatechin(EGC)

[Synonym ]:
EGC
MFCD00075939
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

Biological Activity

[Description]:

(-)-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].

[Related Catalog]:

Natural Products >> Flavonoids

Research Areas >> Others

[References]

[1]. Wang N, et al. (-)-Epigallocatechin-3-gallate Inhibits Fibrillogenesis of Chicken Cystatin. J Agric Food Chem. 2015 Jan 26

[2]. Chung SS, et al. Curcumin and Epigallocatechin Gallate Inhibit the Cancer Stem Cell Phenotype via Down-regulation of STAT3-NFκB Signaling. Anticancer Res. 2015 Jan;35(1):39-46.

[3]. Lee P, et al. Effects of Epigallocatechin gallate against Enterococcus faecalis biofilm and virulence. Arch Oral Biol. 2015 Mar;60(3):393-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
685.6±55.0 °C at 760 mmHg

[ Melting Point ]:
208-210°C

[ Molecular Formula ]:
C₁₅H₁₄O₇

[ Molecular Weight ]:
306.267

[ Flash Point ]:
368.5±31.5 °C

[ Exact Mass ]:
306.073944

[ PSA ]:
130.61000

[ LogP ]:
-0.10

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.776

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KB5100000

CHEMICAL NAME :: Epigallocatechol

CAS REGISTRY NUMBER :: 970-74-1

LAST UPDATED :: 198912

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C15-H14-O7

MOLECULAR WEIGHT :: 306.29

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Human HeLa cell

DOSE/DURATION :: 25 mg/L

REFERENCE :: PYTCAS Phytochemistry. An International Journal of Plant Biochemistry. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1961- Volume(issue)/page/year: 27,1017,1988

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
KB5100000

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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