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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: 2026-06-30 12:28:43
Epicatechin gallate inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.

Name	(-)-epicatechin-3-O-gallate
Synonyms	MFCD00075936 3-O-Galloylgatechin icatechin gallate,froM een tea (-)-icatecholgallate Epicatechol, 3-gallate, (-)- (8CI) Cathechin 3-gallate (-)-3,4,5-Trihydroxybenzoic acid [(2R)-3,4-dihydro-5,7-dihydroxy-2α-(3,4-dihydroxyphenyl)-2H-1-benzopyran]-3α-yl ester (2H)-benzopyran-3,5,7-triol 3-gallate (-)ICATECHIN 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 l-icatechingallate ICATECHIN GALLATE(ECG) FROM EEN TEA BY HPLC BENZOIC ACID, 3,4,5-TRIHYDROXY-, 2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-5,7-DIHYDROXY-2H-1-BENZOPYRAN-3-YL ESTER, (2R-CIS) i-Catechin 3-O-gallat (-)-icatechin gallate in stock Factory 3,4-Dihydro-2α-(3,4-dihydroxyphenyl)-3β-(galloyloxy)-2H-1-benzopyran-5,7-diol ICATECHIN GALLATE, (-) 3-Galloyl-(-)-icatechin dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-ylester (-)-CIS-3,3',4',5,7-PENTAHYDROXYFLAVANE 3-GALLATE (-)-ECG:BENZOICACID, 3,4,5- TRIHYDROXY-, 2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-5,7-DIHYDROXY-2H-1-BENZOPYRAN-3-YLESTER, (2R-CIS) benzoicacid,3,4,5-trihydroxy-,2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydr ECG)-icatechin (-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallate ICATECHIN GALLATE, (-)-(P) L-ECG ECG，(-)-icatechin gallate Gallic acid (2R)-2α-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3β-yl ester 3,4,5-Trihydroxybenzoic acid [(2R)-2α-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran]-3α-yl ester 3-gallate,(-)-icatecho (-)-epicatechin-3-gallate cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1 Aids-000675 icatechol, 3-gallate (-)-epicatechin gallate 3-O-Galloylicatechin icatechol,gallate (-)-icatechin gallate/ECG (−)-Epicatechin gallate (-)-cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate (-)-CIS-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-1(2H)-BENZOPYRAN-3,5,7-TRIOL 3-GALLATE (-)-icatechin gallate 1-5 (2r-cis)-oxy-2h-1-benzopyran-3-yleste Aids000675 Teatannin (-)-cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate, (-)-cis-3,3μ,4μ,5,7-Pentahydroxyflavane 3-gallate (2R)-2α-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3β,5,7-triol 3-(3,4,5-trihydroxybenzoate) 3-Galloyl-(2R,3R)-(-)-icatechin ICATECHIN MONOGALLATE (2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate Epicatechin gallate good price (-)-icatechin gallate 1-5 ICATECHIN GALLATE (-)-ICATECHIN GALLATE icatechinegallate (-)-icatechin gallate from een tea Benzoic acid, 3,4,5- trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-ylester, (2R-cis)-, ICATECHIN GALLATE, (-)- SNAP-N-SHOOT 0.1mg/ml(P) 3,4,5-Trihydroxybenzoic Acid (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl Ester Nsc636594 (2R,3R)-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-1(2H)-BENZOPYRAN-3,5,7-TRIOL 3-(3,4,5-TRIHYDROXYBENZOATE) (2R)-3,4-Dihydro-2α-(3,4-dihydroxyphenyl)-2H-1-benzopyran-3α,5,7-triol 3-(3,4,5-trihydroxybenzoate) ECG Benzoic acid,3,4,5-trihydroxy-, (2R,3R)-2-(3,4 (−)-Epicatechin gallate,from green tea (-)-icatechinGallate> 8-methoxy-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydrochrysen-2(1h)-one (-)-Epicatechingallate (-)-ECG (-)-icatechin gallate (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate)

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.

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

Precursor 8
63604-98-8 1486-48-2 1486-47-1 20728-73-8
87292-49-7 87292-54-4 732298-08-7 732298-11-2
DownStream 10
108907-44-4 1707-75-1 621-54-5 31129-95-0
31129-94-9 191666-22-5 149-91-7 490-46-0
28543-07-9 6500-64-7

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