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

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

KB3745000

F 

10-23

HS Code 

29329990

MSDS

• Language:English Provider:L-Epicatechin
• Language:English Provider:SigmaAldrich

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 (490-46-0)Related Product Information

• Centchroman
• (-)-Epicatechin gallate
• Triphenylphosphine
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• Hydroxy silicone oil
• Tetrahydro-4H-pyran-4-one
• 2-Phenylphenol
• Procyanidin B1
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• (-)-EPICATECHIN
• PROCYANIDIN B2
• (-)-Epicatechin-pentaacetate,(-)-Epicatechin-pentaacetate,(-)-Epicatechin-pentaacetate
• L-Epicatechin
• Gallocatechin-（4α→8）epicatechin,Gallocatechin-（4α→8）epicatechin,Gallocatechin-（4α→8）epicatechin
• Epigallocatechin-(4β→8)-epicatechin-3-O-gallate ester
• (-)-Epicatechin-3-O-gallate Galloylepicatechin,(-)-Epicatechin-3-O-gallate Galloylepicatechin,(-)-Epicatechin-3-O-gallate Galloylepicatechin
• (-)-EPICATECHIN 3-(4''-O-METHYL)GALLATE,(-)-EPICATECHIN 3-(4''-O-METHYL)GALLATE,(-)-EPICATECHIN 3-(4''-O-METHYL)GALLATE