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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

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About This Item

Empirical Formula (Hill Notation):
C15H14O6
CAS Number:
490-46-0
Molecular Weight:
290.27
Beilstein:
92760
EC Number:
207-710-1
MDL number:
MFCD00075648
UNSPSC Code:
12352205
PubChem Substance ID:
24894431
NACRES:
NA.77

Assay

≥90% (HPLC)

form

powder

mp

240 °C (dec.) (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

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 (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

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

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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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)
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)
Lidija Jakobek et al.
Foods (Basel, Switzerland), 9(1) (2020-01-18)
Earlier studies suggested that traditional apple varieties have quality traits well accepted by consumers and beneficial effects on human health. The aim was to collect 25 traditional apple varieties grown in Croatia and to determine, for the first time in
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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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