COX-1/cyclooxygenase-1 (IC50 = 7.5 μM)
Epicatechin gallate exerts its effects through multiple mechanisms. As a potent antioxidant, it scavenges free radicals and reduces oxidative stress. It can modulate a wide range of membrane proteins, and its bilayer-modifying potency has been tested using gramicidin A (gA) channels as probes. These activities contribute to its potential therapeutic effects.

(-)-Epicatechin gallate has an IC50 of 7.5 μM and >95% inhibitory action against cyclooxygenase-1 (COX-1) at 70 μg/mL[1].
In vitro, epicatechin gallate is a potent antioxidant that can modulate a wide range of membrane proteins. Its bilayer-modifying potency has been tested using gramicidin A (gA) channels as probes. As one of the catechin isomers, it exhibits biological activities similar to other catechins.

(-)-Epicatechin gallate, an active ingredient in Onpi-to, a herbal remedy made of five herbal medicines (dry ginger, ginseng, rhubarb, licorice, and tubers), is one of the components of rhubarb. A three-compartment model was able to fit the plasma concentration versus time curve in rats that had received an intravenous dose of (-)-epicatechin gallate (1.0 mg/kg). assessment of plasma epicatechin gallate's pharmacokinetic characteristics (ECG). The ECG's t1/2α, t1/2β, and t1/2γ are 0.038, 0.291, and 4.033 hours, respectively. The electrocardiogram's CLtot is 4.19 L/h • kg. 12.39 L/kg is the Vdss[2].
In vivo, epicatechin gallate is an active ingredient in various traditional medicines. Its antioxidant and anti-inflammatory properties suggest potential applications in the prevention and treatment of various diseases. It is consumed as part of a regular diet, particularly through green tea consumption.

Moderate consumption of wine is associated with a reduced risk of cancer. Grape plant cell cultures were used to purify 12 phenols: the stilbenoids trans-astringin, trans-piceid (2), trans-resveratroloside, trans-resveratrol, trans-piceatannol, cis-resveratroloside, cis-piceid, and cis-resveratrol; the flavans (+)-catechin, (-)-epicatechin, and epicatechin 3-O-gallate; and the flavan dimer procyanidin B2 3'-O-gallate. These compounds were evaluated for potential to inhibit cyclooxygenases and preneoplastic lesion formation in carcinogen-treated mouse mammary glands in organ culture. At 10 micrograms/ml, trans-astringin and trans-piceatannol inhibited development of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions in mouse mammary glands with 68.8% and 76.9% inhibition, respectively, compared with untreated glands. The latter compound was the most potent of the 12 compounds tested in this assay, with the exception of trans-resveratrol (87.5% inhibition). In the cyclooxygenase (COX)-1 assay, trans isomers of the stilbenoids appear to be more active than cis isomers: trans-resveratrol [50% inhibitory concentration (IC50) = 14.9 microM, 96%] vs. cis-resveratrol (IC50 = 55.4 microM). In the COX-2 assay, among the compounds tested, only trans- and cis-resveratrol exhibited significant inhibitory activity (IC50 = 32.2 and 50.2 microM, respectively). This is the first report showing the potential cancer-chemopreventive activity of trans-astringin, a plant stilbenoid recently found in wine. trans-Astringin and its aglycone trans-piceatannol were active in the mouse mammary gland organ culture assay but did not exhibit activity in COX-1 and COX-2 assays. trans-Resveratrol was active in all three of the bioassays used in this investigation. These findings suggest that trans-astringin and trans-piceatannol may function as potential cancer-chemopreventive agents by a mechanism different from that of trans-resveratrol[1].
Non-cellular assays for epicatechin gallate involve assessing its antioxidant activity using cell-free systems. The compound's ability to scavenge free radicals can be evaluated using DPPH or ABTS radical scavenging assays. Its ability to modulate membrane proteins can be assessed using model membrane systems, such as liposomes or black lipid membranes, with gramicidin A channels as probes.

In vitro cellular assays for epicatechin gallate involve treating cells with the compound and measuring its effects on oxidative stress, inflammation, and cell signaling. Cells are treated with epicatechin gallate and exposed to oxidative stress (e.g., H₂O₂). ROS levels are measured using fluorescent probes such as DCFH-DA. The compound's effects on membrane protein function can be assessed using electrophysiological techniques.

In vivo animal experiments with epicatechin gallate are conducted in models of oxidative stress, inflammation, and other diseases. Animals are treated with epicatechin gallate via oral administration, and markers of oxidative stress and inflammation are measured. The compound's effects on disease progression are evaluated.

(-)-Epicatechin-3-O-gallate (ECG) is a component of rhubarb and an active ingredient in a traditional Chinese medicine compound preparation (rhubarb, licorice, ginseng, ginger, and aconite), which has been used to treat patients with chronic renal failure. This study investigated the pharmacokinetics of ECG in male rats using high-performance liquid chromatography-electrochemical detection (HPLC-ECD). 1. After oral administration of ECG, plasma ECG concentration peaks appeared at 0.065, 0.063, and 0.085 hours, corresponding to doses of 12.5, 25.0, and 50.0 mg/kg, with average concentrations of 49.62, 212.89, and 464.04 ng/ml, respectively. Subsequently, plasma ECG concentrations decreased exponentially. 2. The pharmacokinetic characteristics of ECG were nonlinear, with both Cmax and AUC0-inf values showing nonlinear changes. 2. At doses of 12.5, 25.0, and 50.0 mg/kg, the absolute bioavailability (F) was 1.02%, 1.47%, and 3.30%, respectively. 3. After intravenous ECG administration, plasma ECG concentration decreased with increasing γ elimination half-life (t1/2γ), with a half-life of 4.03 hours. 4. After oral ECG administration, urinary ECG concentration was below the limit of quantification. In addition, within 30 hours after administration, the cumulative excretion of metabolites δ-(3,4-dihydroxyphenyl)-γ-valerolactone and δ-(3-methoxy-4-hydroxyphenyl)-γ-valerolactone was 2.45% and 0.23% of the administered dose, respectively. [2]
Epicatechin gallate has a molecular weight of 442.37 and a molecular formula of C₂₂H₁₈O₁₀. It is a white to off-white solid powder with a purity of ≥98%. The compound is soluble in DMSO and is typically stored at 2-8°C. It is stable under recommended storage conditions. Its CAS number is 1257-08-5.

Epicatechin gallate is a research compound for laboratory use only and is not intended for human therapeutic or diagnostic use. It is generally recognized as safe (GRAS) as a dietary component. Standard laboratory safety precautions should be followed when handling the compound.

[1]. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr Cancer. 2001;40(2):173-9.

[2]. Pharmacokinetics of (-)-epicatechin-3-O-gallate, an active component of Onpi-to, in rats. Biol Pharm Bull. 2003 May;26(5):608-12.

(-)-Epicatechin-3-O-gallate is a gallate ester formed by the condensation of the carboxyl group of gallic acid and the (3R)-hydroxyl group of epicatechin. It is a natural product discovered in Parapiptadenia rigida. It is a metabolite and also an inhibitor of EC 3.2.1.1 (α-amylase) and EC 3.2.1.20 (α-glucosidase). It is a catechin, gallate, and polyphenol compound. Its function is related to (-)-epicatechin and gallic acid. (-)-Epicatechin gallate has been found in tea (Camellia sinensis), peony (Paeonia obovata), and other organisms with relevant data.
Epicatechin gallate ((-)-Epicatechin gallate; CAS 1257-08-5) is a catechin isomer and a potent antioxidant. It can modulate a wide range of membrane proteins and is one of the major polyphenolic compounds found in green tea. It is available from various commercial suppliers for research applications.

C22H18O10

442.37 Exact Mass

442.089

C, 59.73; H, 4.10; O, 36.17

1257-08-5

(-)-Epicatechin;490-46-0

107905

White to off-white solid powder

1.8±0.1 g/cm3

861.7±65.0 °C at 760 mmHg

257-258ºC

305.0±27.8 °C

0.0±0.3 mmHg at 25°C

1.825

2.67

7

10

4

32

649

2

C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

LSHVYAFMTMFKBA-TZIWHRDSSA-N

InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1

[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate

Epicatechin-3-O-gallate; (-)-Epicatechin gallate; 1257-08-5; Epicatechin gallate; (-)-epicatechingallate; (-)-Epicatechin-3-O-gallate; L-Epicatechin gallate; epicatechin monogallate; (-)-Epicatechin-3-gallate; Epicatechin 3-gallate; ECG

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ≥ 30 mg/mL (~67.82 mM)

Solubility in Formulation 1: ≥ 2.17 mg/mL (4.91 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.17 mg/mL (4.91 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.17 mg/mL (4.91 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)