L-Epicatechin
- Product Name
- L-Epicatechin
- CAS No.
- 490-46-0
- Chemical Name
- L-Epicatechin
- Synonyms
- EPICATECHIN;(-)-EPICATECHIN;Epicatechine;EPICATECHIN, (-)-;(2R,3R)-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-1(2H)-BENZOPYRAN-3,5,7-TRIOL;Kakaol;(-)-EC;(+)-EC;Colatein;NSC 81161
- CBNumber
- CB0454852
- Molecular Formula
- C15H14O6
- Formula Weight
- 290.27
- MOL File
- 490-46-0.mol
L-Epicatechin Property
- 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)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 74873
- Product name
- (−)-Epicatechin
- Purity
- certified reference material, <I>Trace</I><B>CERT</B><SUP>®</SUP>, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
- Packaging
- 1 unit
- Price
- $238
- Updated
- 2025/07/31
- Product number
- 68097
- Product name
- (?)-Epicatechin
- Purity
- analytical standard
- Packaging
- 10mg
- Price
- $481
- Updated
- 2025/07/31
- Product number
- 03940590
- Product name
- Epicatechin
- Purity
- primary reference standard
- Packaging
- 10mg
- Price
- $498
- Updated
- 2025/07/31
- Product number
- E1226
- Product name
- (-)-Epicatechin
- Purity
- >97.0%(HPLC)
- Packaging
- 1g
- Price
- $129
- Updated
- 2025/07/31
- Product number
- E1226
- Product name
- (-)-Epicatechin
- Purity
- >97.0%(HPLC)
- Packaging
- 5g
- Price
- $386
- Updated
- 2025/07/31
L-Epicatechin Chemical Properties,Usage,Production
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 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from L-Epicatechin manufacturers
- Product
- L-Epicatechin 490-46-0
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 95%
- Supply Ability
- 100KG
- Release date
- 2025-05-27
- Product
- L-Epicatechin 490-46-0
- Price
- US $5.00-0.50/KG
- Min. Order
- 1KG
- Purity
- 99% hplc
- Supply Ability
- 500TONS
- Release date
- 2025-05-07
- Product
- L-Epicatechin 490-46-0
- Price
- US $5.00-0.50/KG
- Min. Order
- 1KG
- Purity
- 99% hplc
- Supply Ability
- 500TONS
- Release date
- 2025-05-06