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

Properties

• 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)

Description

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves