L-Epicatechin CAS 490-46-0
Introduction：Basic information about L-Epicatechin CAS 490-46-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
L-Epicatechin Basic information
| Product Name: | L-Epicatechin |
| Synonyms: | 3,3',4',5,7-PENTAHYDROXY-FLAVANE;3,3',4',5,7-PENTAHYROXYFLAVONE;3,3',4',5,7-PENTAHYDROXYFLAVAN;(2R,3R)-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-1(2H)-BENZOPYRAN-3,5,7-TRIOL;(-)-epicatecho;(-)-epicatechol;(-)-EPICATECHIN;(+)-EPICATECHIN |
| CAS: | 490-46-0 |
| MF: | C15H14O6 |
| MW: | 290.27 |
| EINECS: | 207-710-1 |
| Product Categories: | chemical reagent;pharmaceutical intermediate;Pharmaceutical Raw Materials;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;chiral;Aromatics;Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;490-46-0 |
| Mol File: | 490-46-0.mol |
L-Epicatechin Chemical Properties
| Melting point | 240 °C (dec.)(lit.) |
| alpha | -55～-65゜(D/20℃)(c=1,CH3OH) |
| Boiling point | 629.2 °C |
| density | 1.593±0.06 g/cm3(Predicted) |
| storage temp. | -20°C |
| solubility | insoluble in H2O; insoluble in EtOH; ≥14.5 mg/mL in DMSO |
| form | Solid |
| pka | 9.54±0.10(Predicted) |
| color | White to Light yellow to Light orange |
| Optical Rotation | Consistent with structure |
| biological source | green tea |
| Water Solubility | Soluble in water or alcohol |
| Merck | 13,1912 |
| BRN | 92760 |
| Stability: | Hygroscopic |
| Major Application | metabolomics vitamins, nutraceuticals, and natural products |
| Cosmetics Ingredients Functions | ANTIOXIDANT HAIR DYEING ORAL CARE SKIN CONDITIONING - MISCELLANEOUS SKIN PROTECTING DEODORANT ASTRINGENT |
| 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 |
| InChIKey | PFTAWBLQPZVEMU-UKRRQHHQSA-N |
| SMILES | O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3ccc(O)c(O)c3 |
| LogP | 0.490 (est) |
| CAS DataBase Reference | 490-46-0(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| RTECS | KB3745000 |
| F | 10-23 |
| HS Code | 29329990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Description | (−)-Epicatechin is a polyketide synthase-derived polyphenol flavonoid that has been found in T. cacao and has diverse biological activities. It scavenges DPPH radicals in a cell-free assay when used at a concentration of 5 μM. (−)-Epicatechin inhibits COX-1 (IC50 = 3.2 μM). It acts synergistically with epigallocatechin gallate to induce apoptosis in, and reduce the proliferation of, PC-9 lung cancer cells when used at a concentration of 200 μM. (−)-Epicatechin (80 mg/kg) reduces LPS-induced increases in plasma creatinine and urea levels in a rat model of renal inflammation. |
| Chemical Properties | white to light yellow crystal powde |
| Uses | Potent antioxidant and antineoplastic agent. |
| Uses | Catechin is a polyphenolic flavonoid that has been isolated from a variety of natural sources including tea leaves, grape seeds, and the wood and bark of trees such as acacia and mahogany. Catechin is a more potent antioxidant than ascorbate or α-tocopherol in certain in vitro lipid peroxidation assays. (?)-Epicatechin is a 2R,3R stereoisomer of catechin. Like catechin, (?)-epicatechin is a powerful antioxidant. It inhibits cyclooxygenase 1 (IC50 = 3.2 μM). Also, at 100 μM, (?)-epicatechin induces apoptosis in human adenocarcinoma PC-9 cells and stimulates the inhibition of tumor necrosis factor-α release from BALB-c/3T3 cells treated with epigallocatechin gallate. |
| Uses | An antioxidant and natural product from green tea |
| Definition | ChEBI: A catechin with (2R,3R)-configuration. |
| 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. |
| Biochem/physiol Actions | This antioxidant is found in chocolate. (-)-Epicatechin is linked with cardiovascular effects. It is considered as a dependable standard due to its availability in cacao seeds and cocoa products. The halogenating activity of myeloperoxidase can be restored by (-)-epicatechin. |
| 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. |
L-Epicatechin Preparation Products And Raw materials
| Preparation Products | Procyanidin B1 |
