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Dayang Chem (Hangzhou) Co., Ltd.
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Henan Tianfu Chemical Co., Ltd.
China
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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: 2026-06-30 12:41:19
(-)-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)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol ICATECHIN, (+) (-)-cis-3,3μ,4μ,5,7-Pentahydroxyflavane, (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol icatechinicatechol (-)-3 3' 4' 5 7-Pentahydroxyflavan (−)-cis-3,3',4',5,7-Pentahydroxyflavane i-catechol (-)-CIS-3,3',4',5,7-PENTAHYDROXYFLAVANE 2-(3,4-dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromene 2-(3,4-dihydroxyphenyl)-3,4-dihydro-(2r-cis)-2h-1-benzopyran-7-triol icatechine (-)-ICATECIN EC L-icatechin 2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol (2R,3R)-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-1(2H)-BENZOPYRAN-3,5,7-TRIOL Acacatechin 1-ICATECHIN 2H-1-Benzopyran-3,5,7-triol, 2 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol EC, L-icatechin (2R)-2α-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3α,5,7-triol (-)-icatechin (EC) icatechol CIS-2-[3,4-DIHYDROXYPHENYL]-3,4-DIHYDRO-2H-1-BENZOPYRAN-3,5,7-TRIOL (-)Epicatechin (2R,3R)-2-(3,4-dihydroxyphenyl)chroman-3,5,7-triol Kakaol (2R,3R)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol (-)-3,5,7,3',4'-PENTAHYDROXYFLAVAN EENTEAICATECHIN 2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol L-icatechin -0 Teacatechin I (-)-icatechol 3,3',4',5,7-PENTAHYDROXY-FLAVANE (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol 3,3',4',5,7-PENTAHYROXYFLAVONE 3,3',4',5,7-PENTAHYDROXYFLAVAN ICATECHIN l-acacatechin L(-)-icatechin 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-cis) Colatein (3,4-dihydroxyphenyl)-3,4-dihydro-,(2R-cis) icatechin,-cis-3,3′,4′,5,7-Pentahydroxyflavane, (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol (+)-ICATECHIN L-ICATECHIN epicatechin ICATECHIN, (-) L-icatechin，EC EINECS 207-710-1 L-(-)-ICATECHIN [2R,(-)]-2α-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3α,5,7-triol Table son tea (2R,3R)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol (-)-ICATECHIN CRYSTALLINE L(-)-icatechin, mixt. of ca. L(-)-icatechin and ca. Catechin (-)-icatecho (−)-Epicatechin,from green tea CIS-3,3',4',5,7-PENTAHYDROXYFLAVANE (-)-ICATECHIN EEN TEA L-Epicatechin l-icatechol MFCD00075648 3,5,7,3',4'-PENTAHYDROXYFLAVAN (-)-icatechin, >= (-)-ICATECHIN(℃) (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol (-)ICATECHIN (-)-ICATECHIN

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.

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
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

Precursor 8
87292-49-7 29106-51-2 989-51-5 154-23-4
117-39-5 13157-90-9 1392108-91-6 20315-25-7
DownStream 9
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

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