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E1753

Sigma-Aldrich

(−)-Epicatechin

≥90% (HPLC)

Sinônimo(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

Fórmula empírica (Notação de Hill):
C15H14O6
Número CAS:
490-46-0
Peso molecular:
290.27
Beilstein:
92760
Número CE:
207-710-1
Número MDL:
MFCD00075648
Código UNSPSC:
12352205
ID de substância PubChem:
24894431
NACRES:
NA.77

Nível de qualidade

200

Ensaio

≥90% (HPLC)

Formulário

powder

pf

240 °C (dec.) (lit.)

aplicação(ões)

metabolomics
vitamins, nutraceuticals, and natural products

cadeia de caracteres SMILES

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

chave InChI

PFTAWBLQPZVEMU-UKRRQHHQSA-N

Informações sobre genes

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

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Descrição geral

(−)-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.

Aplicação

(−)-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

Ações bioquímicas/fisiológicas

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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
BCCD3979
BCBZ4766
BCBW4134
BCBV8246
BCBS3589V

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(+)-Catechin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1963

(+)-Catechin

(+)-Catechin hydrate ≥96.0% (sum of enantiomers, HPLC)

Sigma-Aldrich

22110

(+)-Catechin hydrate

Epicatechin gallate primary reference standard

03950590

Epicatechin gallate

(−)-Epigallocatechin gallate ≥95%

Sigma-Aldrich

E4143

(−)-Epigallocatechin gallate

(−)-Epigallocatechin analytical standard

Supelco

08108

(−)-Epigallocatechin

(−)-Catechin gallate ≥98% (HPLC), from green tea

Sigma-Aldrich

C0692

(−)-Catechin gallate

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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