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  • Product Name: Catechin
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154-23-4

154-23-4 structure
154-23-4 structure
  • Name: Catechin
  • Chemical Name: (+)-catechin
  • CAS Number: 154-23-4
  • Molecular Formula: C15H14O6
  • Molecular Weight: 290.268
  • Catalog: Biochemical Natural product
  • Create Date: 2018-04-11 08:00:00
  • Modify Date: 2024-01-02 16:44:01
  • Catechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.
Name (+)-catechin
Synonyms (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
(2R,3S)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol
Sunkatol No. 1
(+)-Cianidanol
Dexcyanidanol
2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3S)-
Catechuic acid
3-Cyanidanol, (+)-
(+)-(2R:3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol
(+)-3,3',4',5,7-Flavanpentol Hydrate
Catechin
(2R,3S)-2-(3,4-Dihydroxyphényl)-3,4-dihydro-2H-chromène-3,5,7-triol
(+)-3,3,4,5,7-Flavanpentol
trans-(+)-3,3',4',5,7-Flavanpentol
(+)-Cyanidanol-3
(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol
(+)-Catechin Hydrate
(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
(+)-catechin
(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-chromen-3,5,7-triol
Catechinic acid
2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-trans)-
EINECS 205-825-1
(2R,3S)-2-(3,4-Dihydroxyphenyl)chromane-3,5,7-triol
Cyanidol
D-Catechol
Description Catechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.
Related Catalog
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 in 0.25% w/v sodium carboxy methylcellulose (CMC) 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.
Density 1.6±0.1 g/cm3
Boiling Point 630.4±55.0 °C at 760 mmHg
Melting Point 175-177ºC (anhydrous)(lit.)
Molecular Formula C15H14O6
Molecular Weight 290.268
Flash Point 335.0±31.5 °C
Exact Mass 290.079041
PSA 110.38000
LogP 0.49
Vapour Pressure 0.0±1.9 mmHg at 25°C
Index of Refraction 1.742

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DJ3450000
CHEMICAL NAME :
2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-trans)-
CAS REGISTRY NUMBER :
154-23-4
LAST UPDATED :
199710
DATA ITEMS CITED :
19
MOLECULAR FORMULA :
C15-H14-O6
MOLECULAR WEIGHT :
290.29

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1084 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
68 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
55 gm/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
12150 mg/kg
SEX/DURATION :
female 17-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

MUTATION DATA

TYPE OF TEST :
Sex chromosome loss and nondisjunction
TEST SYSTEM :
Human Lymphocyte
DOSE/DURATION :
500 mg/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 246,205,1991 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-FINLAND:TWA 5 ppm (20 mg/m3);STEL 10 ppm (45 mg/m3) JAN 1993 OEL-THE NETHERLANDS:TWA 5 ppm (20 mg/m3) JAN 1993
Hazard Codes Xi
Risk Phrases R36/37/38
Safety Phrases 26-36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS DJ3450000
HS Code 2932999099
HS Code 2932999099
Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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title: CAS No. 154-23-4 | Chemsrc address: https://www.chemsrc.com/en/baike/1115126.html

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