490-46-0 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.
Check Digit Verification of cas no
The CAS Registry Mumber 490-46-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 0 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 490-46:
(5*4)+(4*9)+(3*0)+(2*4)+(1*6)=70
70 % 10 = 0
So 490-46-0 is a valid CAS Registry Number.
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
490-46-0Relevant articles and documents
Proanthocyanidin glycosides and related polyphenols from cacao liquor and their antioxidant effects.
Hatano, Tsutomu,Miyatake, Haruka,Natsume, Midori,Osakabe, Naomi,Takizawa, Toshio,Ito, Hideyuki,Yoshida, Takashi
, p. 749 - 758 (2002)
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
Nunes, Domingos S.,Haag, Armin,Bestmann, Hans-Juergen
, p. 2183 - 2186 (1989)
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.
Study on in Vitro Preparation and Taste Properties of N-Ethyl-2-Pyrrolidinone-Substituted Flavan-3-Ols
Han, Zisheng,Ho, Chi-Tang,Jiang, Zongde,Lai, Guoping,Qin, Chunyin,Wan, Xiaochun,Wen, Mingchun,Zhai, Xiaoting,Zhang, Hui,Zhang, Liang
, (2022/04/07)
N-ethyl-2-pyrrolidinone-substituted flavan-3-ols (EPSFs) were prepared by an in vitro model reaction, and the taste thresholds of EPSFs and their dose-over-threshold factors in large-leaf yellow tea (LYT) were investigated. The effects of initial reactant
Proanthocyanidin Tetramers and Pentamers from Cinnamomum verum Bark and Their Dentin Biomodification Bioactivities
Jing, Shu-Xi,Alania, Yvette,Reis, Mariana,McAlpine, James B.,Chen, Shao-Nong,Bedran-Russo, Ana K.,Pauli, Guido F.
, p. 391 - 404 (2022/02/16)
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.