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Merck
CN

525952

(−)-Epicatechin

90%

Synonym(s):

(−)-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
EC Number:
207-710-1
UNSPSC Code:
12352200
PubChem Substance ID:
24874522
Beilstein/REAXYS Number:
92760
MDL number:
MFCD00075648

Key Documents

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InChI key

PFTAWBLQPZVEMU-UKRRQHHQSA-N

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

SMILES string

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

assay

90%

optical activity

[α]20/D −54°, c = 1 in acetone: water (1:1)

mp

240 °C (dec.) (lit.)

Gene Information

human ... BACE1(23621), CYP1A2(1544)

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pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
10620JH
07211EH
02008CH
02217AH
06913TE

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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
Aderville Cabassi et al.
Circulation research, 114(11), 1723-1732 (2014-04-02)
Ceruloplasmin antioxidant function is mainly related to its ferroxidase I (FeOxI) activity, which influences iron-dependent oxidative and nitrosative radical species generation. Peroxynitrite, whose production is increased in heart failure (HF), can affect ceruloplasmin antioxidant function through amino acid modification. We
Hsiao-Ching Lin et al.
Journal of natural products, 73(8), 1375-1380 (2010-06-24)
Seven proanthocyanidins (2-8) together with epicatechin (1) were isolated from the EtOH extract of the leaves of Machilus philippinensis. Of these, machiphilitannins A (7) and B (8) are new natural products, with respective IC(50) values of 31.3 (7) and 18.4
Midori Natsume et al.
Free radical biology & medicine, 34(7), 840-849 (2003-03-26)
(-)-epicatechin is one of the most potent antioxidants present in the human diet. Particularly high levels are found in black tea, apples, and chocolate. High intake of catechins has been associated with reduced risk of cardiovascular diseases. There have been
Karen J Murphy et al.
The American journal of clinical nutrition, 77(6), 1466-1473 (2003-06-07)
Flavonoids may be partly responsible for some health benefits, including antiinflammatory action and a decreased tendency for the blood to clot. An acute dose of flavanols and oligomeric procyanidins from cocoa powder inhibits platelet activation and function over 6 h
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