| Identification | More | [Name]
(+/-)-Catechin hydrate | [CAS]
7295-85-4 | [Synonyms]
(+/-)-3,3',4',5,7-FLAVANPENTOL
3,3',4',5,7-FLAVANPENTOL
(+/-)-CATECHIN
CATECHIN
CATECHIN, DL-
CATECHINS
CATECHU
DL-CATECHIN
DL-CATECHIN CATECHINS
TRANS-1,2,4,5-BENZENETETRACARBOXYLIC ACID
TRANS-2-(3,4-DIHYDROXYPHENYL)3,4-DIHYDRO-2H-1-BENZOPYRAN-3,5,7-TRIOL
TRANS-PYROMELLITIC ACID
YK-85 Light Yellow
2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3S)-rel-
(+/-)-Catechin hydrate
trans-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol hydrate
trans-3,3',4',5,7-Pentahydroxyflavane hydrate
trans-3,3μ,4μ,5,7-Pentahydroxyflavane, trans-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol | [EINECS(EC#)]
230-731-2 | [Molecular Formula]
C15H16O7 | [MDL Number]
MFCD00135995 | [Molecular Weight]
308.28 | [MOL File]
7295-85-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
~200 °C (dec.) | [Boiling point ]
630.4±55.0 °C(Predicted) | [density ]
1.593±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
9.54±0.10(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
8-10-23 | [HS Code ]
2932990090 |
| Hazard Information | Back Directory | [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 |
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