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E4018

Sigma-Aldrich

(−)-Epicatechin

≥98% (HPLC), from green tea

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
Beilstein/REAXYS Number:
92760
EC Number:
207-710-1
MDL number:
MFCD00075648
UNSPSC Code:
12352205
PubChem Substance ID:
24894538
NACRES:
NA.77

biological source

green tea

assay

≥98% (HPLC)

mp

240 °C (dec.) (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°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

Gene Information

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

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General description

Epicatechin is a flavanol, that belongs to the class of secondary, polyphenolic plant metabolites.

Application

(-)-Epicatechin has been used:
  • to examine its biological effects in cell lines from human gender-specific cancers
  • to study its antiviral activity
  • to test its ability to regenerate this enzymatic activity both in vitro at the isolated MPO−H2O2−Cl- system and ex vivo in human polymorphonuclear leukocytes (PMNs)

Biochem/physiol Actions

This antioxidant is found in chocolate. (-)-Epicatechin is linked with cardiovascular effects. It is considered as a dependable standard due to its availability in cacao seeds and cocoa products. The halogenating activity of myeloperoxidase can be restored by (-)-epicatechin.

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

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Divergent antiviral effects of bioflavonoids on the hepatitis C virus life cycle
Khachatoorian R, et al.
Virology, 346-355 (2012)
(-)-Epicatechin mediates beneficial effects of flavanol-rich cocoa on vascular function in humans
Schroeter H, et al.
Proceedings of the National Academy of Sciences of the USA, 103(4), 1024-1029 (2006)
(-)-Epicatechin regenerates the chlorinating activity of myeloperoxidase in vitro and in neutrophil granulocytes
Flemmig J, et al.
Journal of Inorganic Biochemistry, 84-91 (2014)
Epicatechins purified from green tea (Camellia sinensis) differentially suppress growth of gender-dependent human cancer cell lines
Ravindranath M H, et al.
Evidence-Based Complementary and Alternative Medicine : ECAM, 3(2), 237-247 (2006)
Fluorescent detection of (-)-epicatechin in microsamples from cacao seeds and cocoa products: Comparison with Folin-Ciocalteu method
Ramirez-Sanchez I, et al.
Journal of Food Lipids, 23(8), 790-793 (2010)
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Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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