CAS Number490-46-0
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; 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
Molecular FormulaC15H14O6
Molecular Weight290.27
Purity≥90 (HPLC)%
Density1.6±0.1 g/cm3
Boiling Point630.4±55.0 °C at 760 mmHg
Melting Point240 °C (dec.) (lit.)
Appearancepowder
EINECS207-710-1
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 490-46-0 |
| Catalog No. | 2A-9022218 |
| Chinese Name | 表儿茶素(EC) |
| 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; 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 |
| Molecular Formula | C15H14O6 |
| Molecular Weight | 290.27 |
| Purity | ≥90 (HPLC) |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 630.4±55.0 °C at 760 mmHg |
| Melting Point | 240 °C (dec.) (lit.) |
| Appearance | powder |
| Water Solubility | Soluble in: methanol |
| Storage Condition | Use and store according to specifications at 2-8°C |
| Application | (-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. (-)-Epicatechin inhibits IL-1β-induced iNOS expression by blocking the nuclear localization of the p65 subunit of NF-κB. |
| EINECS | 207-710-1 |
| PubChem ID | 24894431 |
| MDL Number | MFCD00075648 |
| SMILES | O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3ccc(O)c(O)c3 |
| InChI | 1S/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-/m1/s1 |
| InChI Key | PFTAWBLQPZVEMU-UKRRQHHQSA-N |
| Beilstein/REAXYS | 92760 |
| NACRES Code | NA.77 |
| UNSPSC | 12352205 |
| Hazard Symbols | Transport |
| MSDS | msds/22218_1_490_46_0.pdf |
| Bioactivity | (-)-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 >> Flavonoids Research Areas >> Cancer Research 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 |
| Use of | (-)-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. Properties Articles187 Name (-)-epicatechin Synonym More Synonyms Epicatechin Biological Activity 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 >> Flavonoids Research Areas >> Cancer Research Areas >> Inflammation/Immunology COX-1:3.2 μM (IC50) 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 Molecular Formula C15H14O6 Exact Mass 290.079041 PSA 110.38000 Index of Refraction 1.742 InChIKey PFTAWBLQPZVEMU-UKRRQHHQSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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