03940590

Epicatechin

primary reference standard

Synonym(s):
(−)-Epicatechin, (−)-cis-3,3′,4′,5,7-Pentahydroxyflavane, (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
Empirical Formula (Hill Notation):
C15H14O6
CAS Number:
Molecular Weight:
290.27
Beilstein/REAXYS Number:
92760
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.24

grade

primary reference standard

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

HWI

mp

240 °C (dec.) (lit.)

Featured Industry

Food and Beverages

storage temp.

−20°C

SMILES string

O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3ccc(O)c(O)c3

InChI

1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1

InChI key

PFTAWBLQPZVEMU-UKRRQHHQSA-N

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General description

Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.
Epicatechin is a potential antioxidant flavonoid, which belongs to the catechin family. It is commonly found in monomeric or/and oligomeric forms in green teas, red wine, cocoa products, and various fruits like grape seeds.

Application

Reference Standard in the analysis of herbal medicinal products

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

hazcat

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

Target Organs

Respiratory system

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Structures of (?)-epicatechin glucuronide identified from plasma and urine after oral ingestion of (?)-epicatechin: differences between human and rat
Natsume M, et al.
Free Radical Biology & Medicine, 34, 840-849 (2003)
Uptake and metabolism of epicatechin and its access to the brain after oral ingestion
Mohsen EA.MM, et al.
Free Radical Biology & Medicine, 33, 1693-1702 (2002)
Major flavonoids in grape seeds and skins: antioxidant capacity of catechin, epicatechin, and gallic acid
Yilmaz Y and Toledo.TR
Journal of Agricultural and Food Chemistry, 52, 255-260 (2004)
Rosario Jiménez et al.
Journal of agricultural and food chemistry, 60(36), 8823-8830 (2012-03-24)
Epidemiological studies indicate an inverse relationship between flavanol intake and the risk of cardiovascular disease. Potential mechanisms include their effects on endothelial function and hypertension. A number of studies have shown that flavanol-rich cocoa reduces blood pressure and endothelial dysfunction...
Elena Roura et al.
Journal of agricultural and food chemistry, 53(16), 6190-6194 (2005-08-04)
A rapid liquid chromatography electrospray ionization tandem mass spectrometry with negative ion detection method was developed and validated to determine cocoa flavonoid metabolites in human plasma and urine after the intake of a standard portion of a cocoa beverage. A...

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