CAS 490-46-0|Epicatechin
| Common Name | Epicatechin | ||
|---|---|---|---|
| CAS Number | 490-46-0 | Molecular Weight | 290.268 |
| Density | 1.6±0.1 g/cm3 | Boiling Point | 630.4±55.0 °C at 760 mmHg |
| Molecular Formula | C15H14O6 | Melting Point | 240 °C (dec.)(lit.) |
| MSDS | ChineseUSA | Flash Point | 335.0±31.5 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | (-)-epicatechin |
|---|---|
| Synonym | More Synonyms |
Epicatechin BiologicalActivity
| Description | (-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. (-)-Epicatechin inhibits the IL-1β-induced expression of iNOS by blocking the nuclear localization of the p65 subunit of NF-κB. |
|---|---|
| Related Catalog | Natural Products >>FlavonoidsResearch Areas >>CancerResearch Areas >>Inflammation/Immunology |
| Target | COX-1:3.2 μM (IC50) |
| In Vitro | (-)-Epicatechin exhibits >95% inhibitory activity at 70 μg/mL against cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM[1]. (-)-Epicatechin inhibits the IL-1β-induced expression of iNOS by blocking the nuclear localization of the p65 subunit of NF-κB. In RINm5F cells, (-)-Epicatechin is shown to block the inhibition of insulin release after addition of IL-1β. Additionally, (-)-Epicatechin is shown to inhibit the proliferation of Hodgkin's lymphoma cells and Jurkat T cells, which is attributed to the ability of (-)-Epicatechin to inhibit the binding of NF-κB to DNA in these cells. In human colorectal cancer HCT-116 cells, combining 20 μM Panaxadiol with 150, 200, or 250 μM (-)-Epicatechin results in growth inhibition of 51%, 97%, and 95%, respectively. The combination also increases the apoptosis level by 11.9%, 16.6%, and 25.8%, as examined by annexin V/PI staining[2]. |
| In Vivo | Animals receive 1 mg/kg of (-)-Epicatechin or water (vehicle) via oral gavage (twice daily). Exercise groups undergo 15 days of treadmill exercise. Significant increases in treadmill performance (~50%) and enhanced in situ muscle fatigue resistance (~30%) are observed with (-)-Epicatechin[3]. |
| Animal Admin | Mice[3] 1-year-old, male C57BL/6N mice (n=25) are randomized into four groups. Mice in the (-)-Epicatechin groups 3 and 4 are given 1.0 mg/kg twice a day (morning and evening) for 15 consecutive days, whereas animals in the control groups 1 and 2 receive the vehicle (water). Both (-)-Epicatechin and vehicle are administered via oral gavage[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]. Shay J, et al. Molecular Mechanisms and Therapeutic Effects of (-)-Epicatechin and Other Polyphenols in Cancer, Inflammation, Diabetes, and Neurodegeneration. Oxid Med Cell Longev. 2015;2015:181260. [3]. Nogueira L, et al. (-)-Epicatechin enhances fatigue resistance and oxidative capacity in mouse muscle. J Physiol. 2011 Sep 15;589(Pt 18):4615-31. |
Chemical & Physical Properties
| Density | 1.6±0.1 g/cm3 |
|---|---|
| Boiling Point | 630.4±55.0 °C at 760 mmHg |
| Melting Point | 240 °C (dec.)(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 |
| InChIKey | PFTAWBLQPZVEMU-UKRRQHHQSA-N |
| SMILES | Oc1cc(O)c2c(c1)OC(c1ccc(O)c(O)c1)C(O)C2 |
| Storage condition | 2-8°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
MUTATION DATA - TYPE OF TEST :
- Sister chromatid exchange
- 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
- TYPE OF TEST :
- Sister chromatid exchange
- 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
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 | S26-S36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | KB3745000 |
Articles187
More Articles| Green tea polyphenol (-)-epigallocatechin-3-gallate triggered hepatotoxicity in mice: responses of major antioxidant enzymes and the Nrf2 rescue pathway. Toxicol. Appl. Pharmacol. 283(1) , 65-74, (2015) (-)-Epigallocatechin-3-gallate (EGCG), a constituent of green tea, has been suggested to have numerous health-promoting effects. On the other hand, high-dose EGCG is able to evoke hepatotoxicity. In t... | |
| Identification of Vitis vinifera L. grape berry skin color mutants and polyphenolic profile. Food Chem. 194 , 117-27, (2015) A germplasm set of twenty-five grapevine accessions, forming eleven groups of possible berry skin color mutants, were genotyped with twelve microsatellite loci, being eleven of them identified as true... | |
| Bi-layer composite dressing of gelatin nanofibrous mat and poly vinyl alcohol hydrogel for drug delivery and wound healing application: in-vitro and in-vivo studies. J. Biomed. Nanotechnol. 9(9) , 1495-508, (2013) Present investigation involves the development of a bi-layer dressing of gelatin nanofibrous mat loaded with epigallocatechin gallate (EGCG)/poly vinyl alcohol (PVA) hydrogel and its in-vivo evaluatio... |
Synonyms
| (2R,3R)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol |
| (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol |
| (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol |
| (-)-3 3' 4' 5 7-Pentahydroxyflavan |
| (-)-epicatechin |
| (−)-Epicatechin,from green tea |
| (-)Epicatechin |
| (2R,3R)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol |
| 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R)- |
| L-Epicatechin |
| MFCD00075648 |
| (−)-cis-3,3',4',5,7-Pentahydroxyflavane |
| (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol |
| epicatechin |
| EINECS 207-710-1 |
| EC |
