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E1753

(−)-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
UNSPSC Code:
12352205
NACRES:
NA.77
PubChem Substance ID:
24894431
EC Number:
207-710-1
Beilstein/REAXYS Number:
92760
MDL number:
MFCD00075648
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Quality Level

200

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)

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.

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD3979
BCBZ4766
BCBW4134
BCBV8246
BCBS3589V

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Articles

膳食抗氧化剂

抗氧化剂可保护生物系统免受含氧自由基和氧化还原过渡金属离子（如铁、铜和镉）引起的氧化损伤。

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.

DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

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)
View All Related Papers

Global Trade Item Number

SKUGTIN
E1753-5G04061835544400
E1753-1G04061835544394