Epicatechin

Names

[ CAS No. ]:
490-46-0

[ Name ]:
Epicatechin

[Synonym ]:
(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

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

[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.

[Related Small Molecules]

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

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KB3745000

CHEMICAL NAME :: Epicatechol, (-)-

CAS REGISTRY NUMBER :: 490-46-0

LAST UPDATED :: 199106

DATA ITEMS CITED :: 2

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 :: 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

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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...

Related Compounds

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