(−)-Epicatechin
SIGMA/E1753 - ≥90% (HPLC)
Synonym: (−)-cis-3,3′,4′,5,7-Pentahydroxyflavane; (2R,3R)
CAS Number: 490-46-0
Empirical Formula (Hill Notation): C15H14O6
Molecular Weight: 290.27
EC Number: 207-710-1
MDL Number: MFCD00075648
Linear Formula: C15H14O6
Product Type: Chemical
This picture is provided solely for illustration purposes, it may have been created or edited with AI. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: E1753-5G
| application(s) | metabolomics vitamins, nutraceuticals, and natural products |
| assay | ≥90% (HPLC) |
| form | powder |
| InChI | 1S/C15H14O6/c16-8-4-11(18 |
| InChI key | PFTAWBLQPZVEMU-UKRRQHHQSA |
| mp | 240 °C (dec.) (lit.) |
| Quality Level | 200  |
| SMILES string | O[C@@H]1Cc2c(O)cc(O)cc2O[ |
| 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. |
| 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. |
| Packaging: | 1, 5 g in glass bottle |
| Symbol |  GHS07 |
| Signal word | Warning |
| Hazard statements | H315 - H319 - H335 |
| Precautionary statements | P302 + P352 - P305 + P351 + P338 |
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥90% (HPLC) |
| mp | 240 °C (dec.) (lit.) |
| UNSPSC | 12352205 |