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E1753

(−)-Epicatechin

≥90% (HPLC)

Sinónimos:

(−)-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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Fórmula empírica (notación de Hill):
C15H14O6
Número CAS:
490-46-0
Peso molecular:
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 Segment

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

Clase de almacenamiento

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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