(+)-Catechin hydrate

Names

[ Name ]:
(+)-Catechin hydrate

[Synonym ]:
(2R-trans)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol monohydrate
EINECS 230-731-2
(2R,3S)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol hydrate
2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, hydrate (1:1)
2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3S)-, hydrate (1:1)
MFCD00150865
D-CATECHOL HYDRATE
FK-027-13C,15N2
(+)-Cyanidol-3
D-CATECHIN HYDRATE
(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
D-CATECHIN
CYANIDOL HYDRATE
Cefixoral-13C,15N2
Catechin Hydrate
(+)-Cyanidol-3,(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
（＋）－Catechin Hydrate
(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol hydrate (1:1)
2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol hydrate (1:1)
(+)-C
(2R,3S)-2-(3,4-Dihydroxyphenyl)chromane-3,5,7-triol hydrate (1:1)

Biological Activity

[Description]:

(+)-Catechin hydrate inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.

[Related Catalog]:

Research Areas >> Cancer

Natural Products >> Flavonoids

[Target]

COX-1:1.4 μM (IC50)

[In Vitro]

(+)-Catechin exhibits >95% inhibitory activity at 70 μg/mL against cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM[1]. A dose-dependent reduction in color is observed after 24 hours of treatment with (+)-Catechin, and 54.76% of the cells are dead at the highest concentration of (+)-Catechin tested (160 μg/mL) whereas the IC50 of (+)-Catechin is achieved at 127.62 μg/mL (+)-Catechin. A dose- and time-dependent increase in the induction of apoptosis is observed when MCF-7 cells are treated with (+)-Catechin. When compare to the control cells at 24 hours, 40.7 and 41.16% of the cells treated with 150 μg/mL and 300 μg/mL (+)-Catechin, respectively, undergo apoptosis. The expression levels of Caspase-3, -8, and -9 and p53 in MCF-7 cells treated with 150 μg/mL (+)-Catechin for 24 h increase by 5.81, 1.42, 3.29, and 2.68 fold, respectively, as compare to the levels in untreated control cells[2].

[In Vivo]

Animals treated with (+)-Catechin at the lowest tested dose, i.e., 50 mg/kg, p.o. have spent comparatively more time in exploring the novel object in the choice trial, however, the difference is not statistically significant. (+)-Catechin prevents the time-induced episodic memory deficits in a dose-dependent manner, the most effective being 200 mg/kg, p.o.. Treatment with (+)-Catechin prevents the rise in MPO level compare to DOX alone treatment group (21.98±9.44 and 36.76±4.39% in the hippocampus and the frontal cortex respectively)[3].

[Cell Assay]

The Cell viability assay is performed to assess the toxicity of different concentrations of (+)-Catechin on MCF-7 cells. Briefly, MCF-7 cells (2×104 cells/well) are plated in 96-well plates and treated with 0 μg/mL (+)-Catechin and 160 μg/mL (+)-Catechin for 24 hours. Then, 40 μL of the Cell Titer Blue solution is directly added to the wells and incubated at 37°C for 6 hours. The fluorescence is recorded with a 560 nm/590 nm (excitation/emission) filter set using a microplate fluorescence reader, and the IC50 is calculated. Quadruplet samples are run for each concentration of (+)-Catechin in three independent experiments[2].

[Animal admin]

Rats[3] Twelve weeks old, healthy male rats weighing 200 to 230 g are used in this study. Rats are divided into four experimental groups (n=9 each) for one vehicle and three groups of (+)-Catechin (three doses). The doses of (+)-Catechin are prepared at 50, 100, 200 mg/kg and administered orally for 7 days prior to and during the experimental trials. Episodic memory, the conscious memory of the past experiences is evaluated in this study[3].

[References]

[1]. Waffo-Téguo P, et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr Cancer. 2001;40(2):173-9.

[2]. Alshatwi AA. Catechin hydrate suppresses MCF-7 proliferation through TP53/Caspase-mediated apoptosis. J Exp Clin Cancer Res. 2010 Dec 17;29:167.

[3]. Cheruku SP, et al. Catechin ameliorates doxorubicin-induced neuronal cytotoxicity in in vitro and episodic memory deficit in in vivo in Wistar rats. Cytotechnology. 2018 Feb;70(1):245-259.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
630.4ºC at760mmHg

[ Melting Point ]:
175-177ºC

[ Molecular Formula ]:
C₁₅H₁₄O_6.xH₂O

[ Molecular Weight ]:
308.283

[ Flash Point ]:
335ºC

[ Exact Mass ]:
308.089600

[ PSA ]:
119.61000

[ LogP ]:
1.48180

[ Vapour Pressure ]:
9.29E-17mmHg at 25°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

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