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

biological source

green tea

optical activity

Consistent with structure

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

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

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.

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

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• (-)-Epicatechin gallate
• 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