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1257-08-5

1257-08-5 structure
1257-08-5 structure
  • Name: (-)-Epicatechin gallate
  • Chemical Name: (-)-epicatechin-3-O-gallate
  • CAS Number: 1257-08-5
  • Molecular Formula: C22H18O10
  • Molecular Weight: 442.372
  • Catalog: Biochemical Plant extracts
  • Create Date: 2018-02-25 08:00:00
  • Modify Date: 2024-01-02 13:58:32
  • Epicatechin gallate inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.

Name (-)-epicatechin-3-O-gallate
Synonyms 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
Description Epicatechin gallate inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.
Related Catalog
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.

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

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
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