490-46-0

Basic information

• Product Name: L-Epicatechin
• Synonyms: (-)-EPICATECHIN;(+)-EPICATECHIN;EPICATECHIN;EPICATECHIN, (-)-;EPICATECHIN, (+)-;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
• CAS NO: 490-46-0
• Molecular Formula: C₁₅H₁₄O₆
• Molecular Weight: 290.27
• EINECS: 207-710-1
• Product Categories: Pharmaceutical Raw Materials;chiral;Aromatics;Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 490-46-0.mol
• Article Data: 58

Chemical Properties

• Melting Point: 240 °C (dec.)(lit.)
• Boiling Point: 630.4 °C at 760 mmHg
• Flash Point: 335°C
• Appearance: White to light yellow crystal powder
• Density: 1.593g/cm³
• Storage Temp.: 2-8°C
• Solubility: insoluble in H2O; insoluble in EtOH; ≥14.5 mg/mL in DMSO
• PKA: 9.54±0.10(Predicted)
• Water Solubility: Soluble in water or alcohol
• Merck: 13,1912
• BRN: 92760
• CAS DataBase Reference: L-Epicatechin(CAS DataBase Reference)
• NIST Chemistry Reference: L-Epicatechin(490-46-0)
• EPA Substance Registry System: L-Epicatechin(490-46-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: KB3745000
• F: 10-23
• Hazardous Substances Data: 490-46-0(Hazardous Substances Data)

Usage

Description

L-Epicatechin, also known as (-)-Epicatechin, is a polyketide synthase-derived polyphenol flavonoid that has been found in various natural sources such as T. cacao, tea leaves, grape seeds, and the wood and bark of trees like acacia and mahogany. It is a 2R,3R stereoisomer of catechin and possesses a chemical structure that includes an oxygenated heterocycle with a 4-hydroxyl group linked with two aromatic rings. L-Epicatechin is a powerful antioxidant and exhibits diverse biological activities.

Uses

Used in Pharmaceutical Applications:
L-Epicatechin is used as an antioxidant and natural product from green tea for its potent antioxidant properties, which are more effective than ascorbate or α-tocopherol in certain in vitro lipid peroxidation assays. It inhibits cyclooxygenase 1 (IC50 = 3.2 μM) and 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.
Used in Nutraceutical Applications:
L-Epicatechin is used as a nutraceutical ingredient for its health-promoting properties, including its ability to scavenge DPPH radicals in a cell-free assay when used at a concentration of 5 μM. It also reduces LPS-induced increases in plasma creatinine and urea levels in a rat model of renal inflammation when administered at a dosage of 80 mg/kg.
Used in Food and Beverage Industry:
L-Epicatechin is used as an additive in the food and beverage industry for its antioxidant properties, which help in preserving the freshness and quality of the products. It is abundantly present in cacao and cacao products, contributing to their health benefits and unique flavor profile.
Used in Cosmetics Industry:
L-Epicatechin is used as an active ingredient in the cosmetics industry for its antioxidant and anti-inflammatory properties. It can be incorporated into skincare products to help protect the skin from environmental stressors and promote a healthy, youthful appearance.

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.

InChI:InChI=1/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

Synthetic route

(+/-)-epicatechin (154-23-4, 490-46-0, 7295-85-4, 13392-26-2, 17334-50-8, 18829-70-4, 35323-91-2, 72690-97-2) → (+)-epicatechin (35323-91-2) + (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0)

Conditions	Yield
With CHIRAL PAKIC In ethanol; hexane at 20℃; Resolution of racemate;	A 85% B 84%
With CHIRAL PAK IC (250 X 4.6) mm, 5μ column In methanol at 25℃; Product distribution / selectivity; Resolution of racemate;
With CHIRAL PAK In methanol at 25℃; Resolution of racemate;

5,7,3',4'-tetra-O-benzylepicatechin (87292-49-7) → (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0)

Conditions	Yield
With 5% Pd(OH)2/C; hydrogen In tetrahydrofuran; methanol; water at 20℃; for 0.5h;	69%
With hydrogen; palladium(II) hydroxide In ethyl acetate at 20℃; for 40h;
With hydrogen; palladium(II) hydroxide In ethyl acetate at 20℃; for 40h;	0.010 mg

C50H42O6 → (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0) + catechin (154-23-4)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol; ethyl acetate at 20 - 55℃;	A 55% B n/a

(-)-epicatechin gallate (863-03-6, 10517-25-6, 13445-34-6, 17431-25-3, 20819-16-3, 25615-05-8, 130405-40-2, 1257-08-5) → (-)-(2R,3R,4R)-3,4,5,7,3',4'-hexahydroxyflavan + (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0)

Conditions	Yield
With Diaporthe sp In methanol at 27℃; for 24h;	A 53% B 13%

procyanidin B1 (20315-25-7) → (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0) + catechin (154-23-4)

Conditions	Yield
With sodium cyanoborohydride In trifluoroacetic acid at 0℃; for 1h; Title compound not separated from byproducts;	A 21% B 20%

procyanidin B2 (29106-49-8) → (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0)

Conditions	Yield
With hydrogenchloride for 0.5h; heating on a boiling water bath;
Multi-step reaction with 2 steps 1: ethanol / 1 h / boiling water bath 2: Raney nickel / ethanol / 2 h / Ambient temperature View Scheme

Upstream product

• 29106-49-8 procyanidin B₂ 
• 23567-23-9 procyanidin B₃ 
• 29106-51-2 procyanidin B₄ 
• 88038-12-4 Cinnamtannin B₁ 
• 88057-90-3 epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin-(4β->8,2β->O->7)-epicatechin-(4α->8)-epicatechin 
• 88082-60-4 cinnamtannin B-1 
• 114715-49-0 (epi)afzelechin‐(4‐8)‐(epi)catechin 
• 79199-56-7 gallocatechin-(4α->8)-epicatechin 
• 97775-90-1 Camelliatannin A 
• 88038-15-7 epicatechin-(4β->6)-epicatechin-(2β->O->7, 4β->8)-epicatechin-(4β->8)-epicatechin 
• 68-11-1 mercaptoacetic acid 
• 82916-01-6 proanthocyanidin B₆ 
• 108907-44-4 (-)-(2R,3R)-5,7-dihydroxy-2-(3',4'-dihydroxy-phenyl)chroman-3-yl 3'',5''-dihydroxy-4''-methoxybenzoate 
• 103303-00-0 (-)-epi-catechin 3-O-β-D-glucopyranoside 

Downstream Products

• 16198-01-9 (+/-)-epicatechol pentaacetate 
• 7295-85-4 catechin 
• 29441-79-0 4-methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6,7-dione 
• 37064-32-7 5,7,3',4'-tetra-O-methylepicatechin-4β,8-(5,7,3',4'-tetra-O-methylepicatechin) 
• 105561-65-7 octa-O-methylprocyanidin B-5 
• 51196-02-2 5,7,3',4'-tetra-O-methylepicatechin 
• 103215-49-2 (-)-epicatechin 6-C-β-D-glucopyranoside 
• 103215-48-1 (-)-epicatechin 8-C-β-D-glucopyranoside 
• 1707-75-1 2,2-diphenyl-1-picrylhydrazine 
• 85022-67-9 cinchonain Id 
• 85022-69-1 epicatechin-(7,8-bc)-4α-(3,4-dihydroxyphenyl)-dihydro-2(3H)-pyranone 
• 78306-10-2 (2R,3S,4R)-2,3-trans-3,4-cis-3,3',4',7-tetrahydroxy-4-<(2R,3R)-2,3-cis-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan 
• 78306-08-8 (2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',7-tetrahydroxy-4-<(2R,3R)-2,3-cis-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan 
• 97775-91-2 Camelliatannin B 

Relevant articles and documents

Proanthocyanidin glycosides and related polyphenols from cacao liquor and their antioxidant effects.

Purification of polar fractions from cacao liquor extracts gave 17 phenolics including four new compounds. The new compounds were characterized as a C-glycosidic flavan, an O-glycoside of a dimeric and two O-glycosides of trimeric A-linked proanthocyanidins, on the basis of spectroscopic data. Isolated polyphenols showed inhibitory effects on nicotinamide adenine dinucleotide phosphate-dependent lipid peroxidation in microsomes and on the autoxidation of linoleic acid. These effects were attributed to the radical-scavenging activity in the peroxidation chain reactions, based on the findings that the cacao polyphenols effectively scavenged the 1,1-diphenyl-2-picrylhydrazyl radical.

TWO PROANTHOCYANIDINS FROM THE BARK OF DALBERGIA MONETARIA

Key Word Index - Dalbergia monetaria; Leguminosae-Papilionoideae; proanthocyanidin dimers.Abstract - In a chemical investigation of the bark of Dalbergia moneteria the two new proanthocyanidins (2R,3R,4R)-3,3',4',7-tetrahydroxyflavan-(4β->8)-epicatechin and (2R,3R,4R)-3,4',7-trihydroxyflavan-(4β->8)-epicatechin were isolated.

Proanthocyanidin Tetramers and Pentamers from Cinnamomum verum Bark and Their Dentin Biomodification Bioactivities

To enable the further exploration of structure-activity relationships (SARs) of proanthocyanidins (PACs) with dentin biomodification abilities, Cinnamomum verum was selected for scaled-up purification of mixed A-/B-type, medium-size PAC oligomers. Sequential purification by centrifugal partition chromatography (CPC), Sephadex LH-20, and semiprep HPLC chromatography yielded four underivatized tetrameric (5-8) and two pentameric (9-10) PACs. Their unambiguous structural characterization involved extensive spectral and chemical degradation approaches to show that epicatechin units are connected by plant-specific combinations of doubly linked A- and singly linked B-type interflavanyl bonds. The biomechanical properties (via dynamic mechanical analysis) and physicochemical structure (via infrared spectroscopy) were assessed to evaluate the biomodification potency of PAC-treated collagen in a preclinical dentin model. This study revealed that (4→8) versus (4→6) bonds in PAC interflavan linkages have limited influence on biomechanical outcomes of dentin. By exhibiting a 25-fold increase in the complex modulus of treated dentin compared to control, aesculitannin E (5) was found to be the most potent PAC known to date for enhancing the mechanical properties of dentin in this preclinical model.

Benzophenone Glucosides and B-Type Proanthocyanidin Dimers from Zambian Cassia abbreviata and Their Trypanocidal Activities

Two benzophenone glucosides (1 and 2), five flavan-3-ol dimers (5–9), and 17 known compounds (3, 4, and 10–24) were identified from the bark extract of Cassia abbreviata. The chemical structures display two points of interest. First, as an unusual charact