(+)-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

Articles

Chemical genetics reveals a complex functional ground state of neural stem cells.

Nat. Chem. Biol. 3(5) , 268-273, (2007)

The identification of self-renewing and multipotent neural stem cells (NSCs) in the mammalian brain holds promise for the treatment of neurological diseases and has yielded new insight into brain canc...

Exogenous acetaldehyde as a tool for modulating wine color and astringency during fermentation.

Food Chem. 177 , 17-22, (2015)

Wine tannins undergo modifications during fermentation and storage that can decrease their perceived astringency and increase color stability. Acetaldehyde acts as a bridging compound to form modified...

Retaining Oxidative Stability of Emulsified Foods by Novel Nonmigratory Polyphenol Coated Active Packaging.

J. Agric. Food Chem. 64 , 5574-82, (2016)

Oxidation causes lipid rancidity, discoloration, and nutrient degradation that decrease shelf life of packaged foods. Synthetic additives are effective oxidation inhibitors, but are undesirable to con...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.