(±)-Catechin

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

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