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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:
Molecular Weight:
442.37
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
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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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

Signal Word

Warning

Hazard Statements

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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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)
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)
Yali Zhao et al.
Drug discovery today, 17(11-12), 630-635 (2012-03-15)
Catechins containing galloyl moieties are important natural antioxidant compounds. In this paper, we review the multiple mechanisms whereby catechins containing a galloyl moiety can target key proteins to inhibit sexual transmission of HIV-1, as well as HIV-1 fusion, HIV-1 reverse
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 ×
Sven Stadlbauer et al.
Chemical communications (Cambridge, England), 48(67), 8425-8427 (2012-07-14)
Concise synthesis of (-)-epicatechin and its 3-O-gallate is described, illustrating efficacy of the new strategy for catechin-class polyphenols based on assembly of lithiated fluorobenzene and epoxy alcohol followed by a pyran cyclization. 1,3,5-Trifluorobenzene serves as the A-ring equivalent for functionalization

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