(+/-)-Epicatechin

Base Information

• Chemical Name: (+/-)-Epicatechin
• CAS No.: 490-46-0
• Molecular Formula: C15H14 O6
• Molecular Weight: 290.273
• Hs Code.: 29329990
• NSC Number: 81162,81161
• Nikkaji Number: J3.322.115K
• Wikidata: Q105207974
• Mol file: 490-46-0.mol

Synonyms:Epicatechol, (-)-;(.+-.)-Epicatechol;SCHEMBL13350313;NSC81162;NSC-81162;2H-1-Benzopyran-3,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-cis)-

Chemical Property of (+/-)-Epicatechin

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Melting Point: 240 °C (dec.)(lit.)
• Boiling Point: 630.4 °C at 760 mmHg
• PKA: 9.54±0.10(Predicted)
• Flash Point: 335°C
• PSA: 110.38000
• Density: 1.593g/cm³
• LogP: 1.54610
• Storage Temp.: 2-8°C
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥14.5 mg/mL in DMSO
• Water Solubility.: Soluble in water or alcohol
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 290.07903816
• Heavy Atom Count: 21
• Complexity: 364

Purity/Quality:

99% ^*data from raw suppliers

(-)-Epicatechin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O
• Isomeric SMILES: C1[C@H](C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O
• 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.
• 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. An antioxidant and natural product from green tea

Technology Process of (+/-)-Epicatechin

There total 169 articles about (+/-)-Epicatechin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

leucocyanidin (15963-96-9) → catechin (154-23-4,490-46-0,7295-85-4,17334-50-8,18829-70-4,35323-91-2,72690-97-2,13392-26-2)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In methanol; for 6h;

Reference yield: 65.0%

racemic 5,7,3',4'-tetra-O-benzyl-(+/-)-catechin (896121-49-6) → catechin (154-23-4,490-46-0,7295-85-4,17334-50-8,18829-70-4,35323-91-2,72690-97-2,13392-26-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; at 20 - 55 ℃;

Reference yield:

3,3',4',5,7-pentahydroxy flavanone (215257-15-1,17654-26-1,5117-01-1) → catechin (154-23-4,490-46-0,7295-85-4,17334-50-8,18829-70-4,35323-91-2,72690-97-2,13392-26-2)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In methanol; for 24h;

upstream raw materials:

procyanidin B₂

procyanidin B₃

procyanidin B₄

Cinnamtannin B₁

Downstream raw materials:

5,7,3',4'-tetra-O-methylepicatechin-4β,8-(5,7,3',4'-tetra-O-methylepicatechin)

octa-O-methylprocyanidin B-5

5,7,3',4'-tetra-O-methylepicatechin

(-)-epicatechin 6-C-β-D-glucopyranoside

Refernces

Cysteinyl-flavan-3-ol conjugates from grape procyanidins. Antioxidant and antiproliferative properties.

10.1016/S0968-0896(02)00127-X

The research focuses on the synthesis and evaluation of cysteinyl-flavan-3-ol conjugates derived from grape procyanidins. These new antioxidant compounds were prepared by depolymerizing grape polymeric flavanols in the presence of cysteine and were assessed for their antiradical/antioxidant and antiproliferative properties. The reactants included grape polymeric flavanols, cysteine, and other reagents necessary for the depolymerization process and subsequent purification. The analyses used to characterize and evaluate the compounds comprised cation-exchange chromatography, preparative reversed-phase chromatography, nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), and theoretical calculations of bond dissociation enthalpies (BDEs). The experiments also involved the DPPH assay to measure the free radical scavenging activity and an MTT assay to evaluate the antiproliferative activity on human colon carcinoma HT29 cells. The results indicated that the new cysteinyl derivatives showed improved antioxidant efficiency and antiproliferative effects compared to the underivatised (-)-epicatechin.

Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: Importance of hydroxyl groups

10.1016/j.bmc.2010.06.077

The research discusses the synthesis and inhibitory activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin against ribonuclease A (RNase A), with the aim of increasing the number of phenolic hydroxyl groups to enhance inhibition. The study concluded that these novel conjugates were more effective inhibitors of RNase A than catechin and epicatechin, highlighting the importance of phenolic hydroxyl groups in inhibiting ribonucleolytic activity. The research also explored the compounds' anti-angiogenic activity through the chorioallantoic membrane (CAM) assay, finding that the epicatechin-based polyphenols showed inhibition of angiogenin-induced angiogenesis. Chemicals used in the synthesis process included (+)-catechin, (-)-epicatechin, phloroglucinol, resorcinol, LiBr, and various protecting groups such as benzyl ether. The study employed techniques like fluorescence studies, protein-ligand docking, and CD spectroscopic studies to evaluate binding parameters and interactions.

Tannins and related compounds. XXXV. Proanthocyanidins with a doubly linked unit from the root bark of Cinnamomum sieboldii Meisner

10.1248/cpb.33.4338

The research focused on the isolation and structural elucidation of proanthocyanidins from the root bark of Cinnamomum sieboldii Meisner, a plant belonging to the Lauraceae family. The purpose of the study was to determine the structures of proanthocyanidin trimers and to clarify the composition of higher oligomeric proanthocyanidins in this plant. The researchers used acid-catalyzed thiolytic degradation, proton and carbon-13 nuclear magnetic resonance analyses to establish the structures of the compounds. They isolated a trimer, two tetramers, and a pentamer, and demonstrated the presence of (-)-epicatechin, (+)-catechin, and known proanthocyanidins B-1, B-2, and B-5, among others. The conclusions highlighted that the root bark of C. sieboldii contains large amounts of proanthocyanidins with a doubly linked bisflavanoid (A-type) unit, accompanied by minor singly linked procyanidins, and that the composition of proanthocyanidins in C. sieboldii is similar to that in C. zeylanicum, which is of chemotaxonomical interest. The study also noted that proanthocyanidin trimers 1 and 9 have a sweet taste, contrasting with the astringent taste of other oligomeric proanthocyanidins.