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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

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About This Item

Empirical Formula (Hill Notation):
C15H14O6
CAS Number:
490-46-0
Molecular Weight:
290.27
Beilstein:
92760
EC Number:
207-710-1
MDL number:
MFCD00075648
UNSPSC Code:
85151701
PubChem Substance ID:
329747844
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.)

application(s)

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

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.
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

Precautionary Statements

P261 - P305 + P351 + P338

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
HWI02311-3
HWI02311-2
HWI02311-1
HWI02311
HWI01708-1

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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)
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)
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
Min-Hsiung Pan et al.
Food & function, 2(2), 101-110 (2011-07-23)
The consumption of green tea has long been associated with a reduced risk of cancer development. (-)-Epicatechin-3-gallate (ECG) or (-)-epigallocatechin-3-gallate (EGCG) are the major antioxidative polyphenolic compounds of green tea. They have been shown to exert growth-inhibitory potential of various
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