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L-Epicatechin

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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
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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)
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)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
KB3745000
10-23
HS Code 
29329990

MSDS

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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 Supplier

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