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ChemicalBook--->CAS DataBase List--->490-46-0

490-46-0

490-46-0 Structure

490-46-0 Structure
IdentificationMore
[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 PropertiesBack 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
[biological source]

green tea
[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 DataBack 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
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

L-Epicatechin(490-46-0).msds
Hazard InformationBack Directory
[Description]

(−)-Epicatechin is a polyketide synthase-derived polyphenol flavonoid that has been found in T. cacao and has diverse biological activities. It scavenges DPPH (Item No. 14805) 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 (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. (−)-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]

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.
Spectrum DetailBack Directory
[Spectrum Detail]

L-Epicatechin(490-46-0)MS
L-Epicatechin(490-46-0)1HNMR
L-Epicatechin(490-46-0)13CNMR
L-Epicatechin(490-46-0)IR1
L-Epicatechin(490-46-0)IR2
L-Epicatechin(490-46-0)Raman
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

490-46-0(sigmaaldrich)
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