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03950590

Epicatechin gallate

primary reference standard

Synonym(s):

(−)-Epicatechin gallate, (−)-cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate, (−)-cis-3,3′,4′,5,7-Pentahydroxyflavane 3-gallate, 3-O-Galloylepicatechin

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About This Item

Empirical Formula (Hill Notation):
C22H18O10
CAS Number:
1257-08-5
Molecular Weight:
442.37
MDL number:
MFCD00075936
UNSPSC Code:
85151701
PubChem Substance ID:
329747845
NACRES:
NA.24

grade

primary reference standard

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

HWI

application(s)

food and beverages

storage temp.

−20°C

SMILES string

Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4ccc(O)c(O)c4

InChI

1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1

InChI key

LSHVYAFMTMFKBA-TZIWHRDSSA-N

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Related Categories

General description

Epicatechin gallate is a polyphenolic compound that belongs to the category of catechins, which are naturally occurring antioxidant flavonoids in green tea. It can find applications as an anticancer, anti-inflammatory agent and cardiovascular agent.
Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Application

Reference Standard in the analysis of herbal medicinal products

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
HWI02233-3
HWI02233-2
HWI02233-1
HWI02233
HWI01496-4

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Scavenging mechanisms of (-)-epigallocatechin gallate and (-)-epicatechin gallate on peroxyl radicals and formation of superoxide during the inhibitory action
Kondo K, et al.
Free Radical Biology & Medicine, 27, 855-863 (1999)
Differential in vitro cytotoxicity of (?)-epicatechin gallate (ECG) to cancer and normal cells from the human oral cavity
Babich.H, et al.
Toxicology in vitro, 19, 231-242 (2005)
Shambhunath Choudhary et al.
Carcinogenesis, 33(4), 876-885 (2012-02-07)
More than 85% of breast cancers are sporadic and attributable to long-term exposure to environmental carcinogens, such as those in the diet, through a multistep disease process progressing from non-cancerous to premalignant and malignant stages. The chemical carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)
Qiu-Hong Zhang et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 880(1), 168-171 (2011-12-14)
A rapid and valid method was developed for simultaneous determination catechin, epicatechin and epicatechin gallate in rat plasmas using scopoletin (103 ng mL(-1)) as an internal standard (IS). The separation was performed on Eclipse plus C18 column (100 mm ×
Suraj P Shrestha et al.
Pharmaceutical research, 29(3), 856-865 (2011-11-10)
The 3,3″-di-O-galloyl ester of procyanidin B2 (B2G2) is a component of grape seed extract that inhibits growth of human prostate carcinoma cell lines. In preparation for studies in mice, its hepatic metabolism was examined in vitro and compared to B2
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