(-)-epicatechin
(-)-Epicatechin (CAS 490-46-0) is a flavonoid compound known for inducing pancreatic β-cell regeneration and modulating nitric oxide (NO) metabolism. It inhibits nitric oxide-related nitrite formation induced by interferon-γ and lipopolysaccharide in mouse macrophages and reduces peroxynitrite-mediated tyrosine nitration in HL-60 human leukemia cells. Additionally, in human endothelial cells (HUVECs), it enhances NO production, displaying vasodilatory properties. In diabetic rat models (alloxan-induced), (-)-epicatechin administration promotes β-cell recovery, reduces hyperglycemia, and prevents β-cell necrosis.
References:
[1]. Chakravarthy BK, Gupta S, Gambhir SS, et al. Pancreatic beta-cell regeneration in rats by (-)-epicatechin. Lancet, 1981, 2(8249): 759-760.
[2]. Wippel R, Rehn M, Gorren AC, et al. Interference of the polyphenol epicatechin with the biological chemistry of nitric oxide- and peroxynitrite-mediated reactions. Biochem Pharmacol, 2004, 67(7): 1285-1295.
[3]. Brossette T, Hundsdörfer C, Kröncke KD, et al. Direct evidence that (-)-epicatechin increases nitric oxide levels in human endothelial cells. Eur J Nutr, 2011, 50(7): 595-599.
[4]. Okushio K, Suzuki M, Matsumoto N, et al. Identification of (-)-epicatechin metabolites and their metabolic fate in the rat. Drug Metab Dispos, 1999, 27(2): 309-316.
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 290.27 |
| Cas No. | 490-46-0 |
| Formula | C15H14O6 |
| Solubility | insoluble in H2O; insoluble in EtOH; ≥14.5 mg/mL in DMSO |
| Chemical Name | (2R,3R)-2-(3,4-dihydroxyphenyl)chroman-3,5,7-triol |
| SDF | Download SDF |
| Canonical SMILES | O[C@H](C1)[C@@H](c(cc2)cc(O)c2O)Oc2c1c(O)cc(O)c2 |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
Quality Control & MSDS
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Chemical structure
