Epicatechin
Epicatechin structure
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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 | Chinese USA | Flash Point | 335.0±31.5 °C | |
| Symbol |
GHS07 |
Signal Word | Warning | |
Use of Epicatechin(-)-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. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | (-)-epicatechin |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| 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 | |
| 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 |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| 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 |
This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.
This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
MUTATION DATA
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This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| 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 |
This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.
This table lists upstream starting materials and downstream derivative products related to this chemical.
| Precursor 8 | |
|---|---|
| DownStream 9 | |
CAS#:87292-49-7
CAS#:29106-51-2
CAS#:989-51-5
CAS#:154-23-4
CAS#:117-39-5![2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)chromen-4-on e Structure](https://image.chemsrc.com/caspic/199/13157-90-9.png)
CAS#:13157-90-9
CAS#:1392108-91-6
CAS#:20315-25-7
CAS#:1707-75-1
CAS#:621-54-5
CAS#:31129-94-9![2-[(2S)-3-(3,4-dihydroxyphenyl)-2-hydroxypropyl]benzene-1,3,5-triol structure](https://image.chemsrc.com/caspic/427/111397-00-3.png)
CAS#:111397-00-3![2(3H)-Furanone,5-[(3,4-dihydroxyphenyl)methyl]dihydro-,(5R)-(9CI) structure](https://image.chemsrc.com/caspic/408/191666-22-5.png)
CAS#:191666-22-5
CAS#:979-92-0
CAS#:29106-49-8
CAS#:12798-57-1
CAS#:4670-05-7This table lists relevant public references with title, journal and publication metadata for this compound.
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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... |
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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... |
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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... |
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| (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 |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What are the downstream products of (-)-epicatechin? |
| A: Related downstream products(CAS) of (-)-epicatechin: 1707-75-1;621-54-5;31129-94-9;111397-00-3;191666-22-5;979-92-0;29106-49-8;12798-57-1;4670-05-7. |
| Q: What is the CAS number of (-)-epicatechin? |
| A: CAS number of (-)-epicatechin is 490-46-0. |
| Q: What is the LogP of (-)-epicatechin? |
| A: LogP of (-)-epicatechin is 0.49. |
| Q: What are the upstream materials of (-)-epicatechin? |
| A: Related upstream materials(CAS) of (-)-epicatechin: 87292-49-7;29106-51-2;989-51-5;154-23-4;117-39-5;13157-90-9;1392108-91-6;20315-25-7. |
| Q: What is the molecular weight of (-)-epicatechin? |
| A: Molecular weight of (-)-epicatechin is 290.268. |
| Q: What are the storage conditions for (-)-epicatechin? |
| A: Storage conditions for (-)-epicatechin: 2-8°C. |
| Q: What is the melting point of (-)-epicatechin? |
| A: Melting point of (-)-epicatechin is 240 °C (dec.)(lit.). |
| Q: What is the English name of (-)-epicatechin? |
| A: The English name of (-)-epicatechin is (-)-epicatechin. |
| Q: What are the uses of (-)-epicatechin? |
| A: Main uses of (-)-epicatechin: (-)-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. |
| Q: What is the SMILES notation of (-)-epicatechin? |
| A: SMILES notation of (-)-epicatechin is Oc1cc(O)c2c(c1)OC(c1ccc(O)c(O)c1)C(O)C2. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| BioBioPha |
| Dayang Chem (Hangzhou) Co., Ltd. |
| naturewill |
| Henan Tianfu Chemical Co., Ltd. |