| Identification | More | [Name]
L-Epicatechin | [CAS]
490-46-0 | [Synonyms]
(2R,3R)-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-1(2H)-BENZOPYRAN-3,5,7-TRIOL
3,3',4',5,7-PENTAHYDROXYFLAVAN
3,3',4',5,7-PENTAHYDROXY-FLAVANE
3,3',4',5,7-PENTAHYDROXYFLAVONE
3,3',4',5,7-PENTAHYROXYFLAVONE
(-)-3,5,7,3',4'-PENTAHYDROXYFLAVAN
3,5,7,3',4'-PENTAHYDROXYFLAVAN
CIS-2-[3,4-DIHYDROXYPHENYL]-3,4-DIHYDRO-2H-1-BENZOPYRAN-3,5,7-TRIOL
(-)-CIS-3,3',4',5,7-PENTAHYDROXYFLAVANE
CIS-3,3',4',5,7-PENTAHYDROXYFLAVANE
(-)-EC
(+)-EC
(-)-EPICATECHIN
(+)-EPICATECHIN
EPICATECHIN
EPICATECHIN, (-)-
EPICATECHIN, (+)-
L-(-)-EPICATECHIN
L-EPICATECHIN
(-)-epicatecho | [EINECS(EC#)]
207-710-1 | [Molecular Formula]
C15H14O6 | [MDL Number]
MFCD00075648 | [Molecular Weight]
290.27 | [MOL File]
490-46-0.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [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. ]
2-8°C
| [solubility ]
insoluble in H2O; insoluble in EtOH; ≥14.5 mg/mL in DMSO | [form ]
neat | [pka]
9.54±0.10(Predicted) | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
KB3745000
| [F ]
10-23 | [HS Code ]
29329990 |
| Hazard Information | Back Directory | [Description]
(−)-Epicatechin is a polyketide synthase-derived polyphenol flavonoid that has been found in T. cacao and has diverse biological activities.1,2,3,4,5 It scavenges DPPH (Item No. 14805) radicals in a cell-free assay when used at a concentration of 5 μM.2 (−)-Epicatechin inhibits COX-1 (IC50 = 3.2 μM).6 It acts synergistically with epigallocatechin gallate (Item No. 70935) to induce apoptosis in, and reduce the proliferation of, PC-9 lung cancer cells when used at a concentration of 200 μM.4 (−)-Epicatechin (80 mg/kg) reduces LPS-induced increases in plasma creatinine and urea levels in a rat model of renal inflammation.5 | [Chemical Properties]
white to light yellow crystal powde | [Uses]
An antioxidant and natural product from green tea | [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]
Potent antioxidant and antineoplastic agent. | [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, hundsd?rfer c, kr?ncke 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. |
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