(-)-Epicatechin gallate

Names

[ Name ]:
(-)-Epicatechin gallate

[Synonym ]:
Benzoic acid, 3,4,5- trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-ylester, (2R-cis)-,
MFCD00075936
Epicatechol, 3-gallate, (-)- (8CI)
ECG
(-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallate
Benzoic acid, 3,4,5-trihydroxy-, (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester
(−)-Epicatechin gallate,from green tea
(2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
Epicatechin gallate
(-)-epicatechin-3-gallate
(-)-Epicatechingallate
(-)-epicatechin gallate
(−)-Epicatechin gallate
(-)-cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate

Biological Activity

[Description]:

Epicatechin gallate inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.

[Related Catalog]:

Natural Products >> Flavonoids

Research Areas >> Cancer

[Target]

COX-1:7.5 μM (IC50)

[In Vitro]

Epicatechin gallate exhibits >95% inhibitory activity at 70 μg/mL against cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM[1].

[In Vivo]

Epicatechin gallate ((-)-Epicatechin-3-O-gallate, ECG), a component of Rhei Rhizoma, is one of the active components of Onpi-to, a herbal medicine composed of five crude drugs (Rhei Rhizome, Glycyrrhizae Radix, Ginseng Radix, Zingiberis Rhizoma and Aconiti Tuber). Following intravenous injection of Epicatechin gallate (1.0 mg/kg) in rats, the plasma concentration vs. time curve is fitted in a three compartment model. Pharmacokinetic parameters for plasma Epicatechin gallate (ECG) are measured. ECG has a t1/2α of 0.038 h, a t1/2βof 0.291 h and a t1/2γ of 4.033 h . The CLtot of ECG is 4.19 L/h • kg. The Vdss is 12.39 L/kg[2].

[Animal admin]

Rats[2] Male Sprague-Dawley rats, obtained at 7 weeks of age (210-245 g) are used. Epicatechin gallate (ECG) is suspended in 0.5% w/v sodium carboxymethylcellulose at 12.5, 25.0 and 50.0 mg/10 mL for oral administration to rats at 10 mL/kg. For intravenous injection in rats at 1.0 mg/kg, an ethanolic solution of Epicatechin gallate is diluted with 10% w/v sodium citrate solution to 1.0 mg/mL; the final concentration of ethanol is 1% v/v[2].

[References]

[1]. Waffo-Téguo P, et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr Cancer. 2001;40(2):173-9.

[2]. Takizawa Y, et al. Pharmacokinetics of (-)-epicatechin-3-O-gallate, an active component of Onpi-to, in rats. Biol Pharm Bull. 2003 May;26(5):608-12.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
861.7±65.0 °C at 760 mmHg

[ Melting Point ]:
257-258ºC

[ Molecular Formula ]:
C₂₂H₁₈O₁₀

[ Molecular Weight ]:
442.372

[ Flash Point ]:
305.0±27.8 °C

[ Exact Mass ]:
442.089996

[ PSA ]:
177.14000

[ LogP ]:
2.67

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.825

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DH9030000

CHEMICAL NAME :: Benzoic acid, 3,4,5-trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H- 1- benzopyran-3-yl ester, (2R-cis)-

CAS REGISTRY NUMBER :: 1257-08-5

LAST UPDATED :: 199309

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H18-O10

MOLECULAR WEIGHT :: 442.40

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JKXXAF Japanese Kokai Tokyo Koho Patents. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #93-944

Safety Information

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

[ Hazard Codes ]:
Xn

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DH9030000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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