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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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

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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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)
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
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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Articles

Analysis of Caffeine and Catechins in Green Tea

Validated HPLC method (based on Ph. Eur. Monograph 2668) for quantifying catechins and caffeine in decaffeinated green tea using a Chromolith® High Resolution RP-18e column with advantages in terms of backpressure and matrix robustness.

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