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| | 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 | | pka | 9.54±0.10(Predicted) | | form | neat | | color | White to Light yellow to Light orange | | Water Solubility | Soluble in water or alcohol | | Merck | 13,1912 | | BRN | 92760 | | Stability: | Hygroscopic | | InChIKey | PFTAWBLQPZVEMU-UKRRQHHQSA-N | | LogP | 0.490 (est) | | CAS DataBase Reference | 490-46-0(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | RTECS | KB3745000 | | F | 10-23 | | HS Code | 29329990 |
| | L-Epicatechin Usage And Synthesis |
| 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 |
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