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490-46-0

490-46-0 structure
490-46-0 structure
  • Name: Epicatechin
  • Chemical Name: (-)-epicatechin
  • CAS Number: 490-46-0
  • Molecular Formula: C15H14O6
  • Molecular Weight: 290.268
  • Catalog: Biochemical Chinese herbal medicine ingredients
  • Create Date: 2018-03-10 08:00:00
  • Modify Date: 2025-08-20 17:24:46
  • (-)-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.
Name (-)-epicatechin
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
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

[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.
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

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
Symbol GHS07
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
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