E1753

Sigma-Aldrich

(−)-Epicatechin

≥90% (HPLC)

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/REAXYS Number:
92760
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥90% (HPLC)

form

powder

mp

240 °C (dec.) (lit.)

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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Related Categories

General description

(−)-Epicatechin (EC) belongs to the group of flavanols and is abundantly present in cacao and cacao products. The chemical structure of EC includes an oxygenated heterocycle with a 4-hydroxyl group linked with two aromatic rings.

Application

(−)-Epicatechin (EC) has been used:
  • as an antioxidant to downregulate nicotinamide adenine dinucleotide phosphate hydrogen (NADPH) oxidase and improve insulin sensitivity in in vivo (high fat-fed mice) and in vitro (HepG2 cells) studies
  • to study its effect on blood pressure, nitric oxide synthase (NOS) activity and anxiety-like behavior on borderline hypertensive rat (BHR) models
  • to test its effect on neuronal survival in the hippocampus of middle-aged rats on swimming training, under oxidative stress
  • to study its antioxidant activity in dark chocolate
  • as a characteristic compound in polyphenols analysis

Packaging

1, 5 g in glass bottle

Biochem/physiol Actions

Epicatechin enhances the skeletal muscle structure in heart failure patients and minimizes cardiometabolic risks. It can be used for treating sarcopenia. Epicatechin reduces myostatin and β-galactosidase and increases the level of markers of muscle growth.

pictograms

Exclamation mark

signalword

Warning

hazcat

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

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

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

Certificate of Origin

Joseph Shay et al.
Oxidative medicine and cellular longevity, 2015, 181260-181260 (2015-07-17)
With recent insight into the mechanisms involved in diseases, such as cardiovascular disease, cancer, stroke, neurodegenerative diseases, and diabetes, more efficient modes of treatment are now being assessed. Traditional medicine including the use of natural products is widely practiced around...
Effects of (-)-epicatechin on molecular modulators of skeletal muscle growth and differentiation
Gutierrez-Salmean G, et al.
The Journal of Nutritional Biochemistry, 25(1), 91-94 (2014)
Effect of dark chocolate on plasma epicatechin levels, DNA resistance to oxidative stress and total antioxidant activity in healthy subjects
Spadafranca A, et al.
The British Journal of Nutrition, 103(7), 1008-1014 (2010)
Michal Kluknavsky et al.
Antioxidants (Basel, Switzerland), 9(2) (2020-01-26)
This study investigated the effects of (-)-epicatechin (Epi) in young male borderline hypertensive rats (BHR) during two weeks of treatment (Epi group, 100 mg/kg/day p.o.) and two weeks post treatment (PE group). Epi reduced blood pressure (BP), which persisted for...
Polyphenols, radical scavenger activity, short-chain organic acids and heavy metals of several plants extracts from ?Bucharest Delta?
Teodor ED, et al.
Chemical Papers, 69(12), 1582-1590 (2015)
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