(+/-)-Catechin hydrate CAS 7295-85-4
(+/-)-Catechin hydrate Basic information
| Product Name: | (+/-)-Catechin hydrate |
| Synonyms: | (±)-Catechin hydrate,trans-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol, trans-3,3′,4′,5,7-Pentahydroxyflavane;trans-3,3μ,4μ,5,7-Pentahydroxyflavane, trans-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol;2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3S)-rel-;trans-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol hydrate;trans-3,3',4',5,7-Pentahydroxyflavane hydrate;(+/-)-Catechin hydrate;Catechin catechin,Cianidanol |
| CAS: | 7295-85-4 |
| MF: | C15H14O6 |
| MW: | 290.27 |
| EINECS: | 230-731-2 |
| Product Categories: | Biochemistry;Flavonoids;Pharmaceutical Raw Materials;Heterocyclic Building Blocks;Benzopyrans;Building Blocks;Chemical Synthesis |
| Mol File: | 7295-85-4.mol |
(+/-)-Catechin hydrate Chemical Properties
| Melting point | ~200 °C (dec.) |
| Boiling point | 630.4±55.0 °C(Predicted) |
| density | 1.593±0.06 g/cm3(Predicted) |
| storage temp. | Sealed in dry,2-8°C |
| solubility | Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly) |
| pka | 9.54±0.10(Predicted) |
| form | Solid |
| color | White to Off-White |
| Merck | 1902 |
| 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+/s3 |
| InChIKey | PFTAWBLQPZVEMU-MJZDCSSWNA-N |
| SMILES | [C@H]1(C2=CC=C(O)C(O)=C2)OC2=CC(O)=CC(O)=C2C[C@@H]1O |&1:0,19,r| |
| LogP | 0.490 (est) |
| CAS DataBase Reference | 7295-85-4(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| F | 8-10-23 |
| HS Code | 2932990090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Uses | (+/-)-Catechin xHydrate is an antioxidant flavonoid. |
| Definition | ChEBI: Catechin is members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives. |
| Biological Activity | Catechin has phytotoxic properties. Racemic catechin may be used in studies on seed germination and plant invasiveness. Catechin and Epigallocatechin gallate (EGCG) may be used with other polyphenol flavonoids to study their effects in oxidation and peroxidation-related processes.', 'Polyphenolic antioxidant. Used in traditional Chinese medicine. |
| Synthesis | 896121-49-6 154-23-4 The general procedure for the synthesis of (2R,3S)-2-(3,4-dihydroxyphenyl)benzopyran-3,5,7-triol from 5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)benzodihydropyran-3-ol was carried out as follows: to a stirred 1:1 (v/v) ethyl acetate and methanol solution of 5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)benzodihydropyran-3-ol (0.24 mmol) at room temperature was added 10% Pd/C catalyst (0.24 mmol) in a mixed solution of ethyl acetate and methanol. alcohol (0.180 g, 0.24 mmol) was added to a slurry of 10% Pd/C catalyst (0.020 g) in a 1:1 (v/v) mixed solution of ethyl acetate and methanol (8 ml). The reaction mixture was stirred at room temperature for 1 hour, then warmed to 50-55 °C and stirred at this temperature overnight. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration and the filtrate was concentrated on a rotary evaporator to give a light brown viscous crude product. The crude product was purified by silica gel column chromatography using 4% methanol/dichloromethane as eluent to afford the off-white powdery target product (2R,3S)-2-(3,4-dihydroxyphenyl)benzopyran-3,5,7-triol (0.045 g, 65% yield). The product was confirmed by ESIMS analysis, m/z: 291 [M+H]+. |
| target | ROS |
| Purification Methods | Crystallise it from hot water and dry it at 100o. [Beilstein 17/8 V 448.] |
| References | [1] Patent: US2015/368223, 2015, A1. Location in patent: Paragraph 0111; 0112; 0113 [2] Patent: CN103833720, 2016, B. Location in patent: Paragraph 0047; 0048 |
(+/-)-Catechin hydrate Preparation Products And Raw materials
| Raw materials | 5,7-BIS(BENZYLOXY)-2-(3,4-BIS(BENZYLOXY)PHENYL)CHROMAN-3-OL(WXG03417)-->Activated carbon-->Methanol-->Palladium-->Ethyl acetate-->Hydrogen |
