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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
Empirical Formula (Hill Notation):
C15H14O6
CAS Number:
Molecular Weight:
290.27
Beilstein:
92760
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

green tea

assay

≥98% (HPLC)

mp

240 °C (dec.) (lit.)

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

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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)

Packaging

1, 5 mg in glass bottle

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

Signal Word

Warning

Hazard Statements

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Divergent antiviral effects of bioflavonoids on the hepatitis C virus life cycle
Khachatoorian R, et al.
Virology, 346-355 (2012)
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)
(-)-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)

Articles

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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