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MedKoo Cat#: 600132 | Name: Epicatechin gallate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Epicatechin gallate (ECG) is a flavan-3-ol, a type of flavonoid, present in green tea. It is also reported in buckwheat and in grape. The tea component epicatechin gallate is being researched because in vitro experiments showed it can reverse methicillin resistance in bacteria like Staphylococcus aureus. If confirmed, this means the combined intake of a tea extract containing this component might also enhance the effectiveness of methicillin treatment against some resistant bacteria in vivo.

Chemical Structure

Epicatechin gallate
Epicatechin gallate
CAS#1257-08-5 (gallate)

Theoretical Analysis

MedKoo Cat#: 600132

Name: Epicatechin gallate

CAS#: 1257-08-5 (gallate)

Chemical Formula: C22H18O10

Exact Mass: 442.0900

Molecular Weight: 442.37

Elemental Analysis: C, 59.73; H, 4.10; O, 36.17

Price and Availability

Size Price Availability Quantity
1g USD 150.00 Ready to ship
5g USD 450.00 Ready to ship
100g USD 2,450.00 Ready to ship
1kg USD 4,450.00 Ready to ship
5kg USD 6,450.00 Ready to ship
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Related CAS #
1257-08-5 (gallate) 490-46-0
Synonym
ECG; Epicatechin 3-gallate; Epicatechin-3-O-gallate.
IUPAC/Chemical Name
[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
InChi Key
LSHVYAFMTMFKBA-TZIWHRDSSA-N
InChi Code
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
SMILES Code
O=C(O[C@H]1[C@@H](C2=CC=C(O)C(O)=C2)OC3=C(C(O)=CC(O)=C3)C1)C4=CC(O)=C(O)C(O)=C4
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
(-)-Epicatechin gallate (ECG) is an inhibitor of cyclooxygenase-1 (COX-1) with IC50 of 7.5 μM.
In vitro activity:
ROS, LDH, MDA, and SOD assays were performed in our study to evaluate the antioxidant activity of ECG. OGD/R induced an ROS level about 2.5-fold to control (normal), whereas ECG downregulated ROS significantly compared with the OGD/R group (P < 0.01) (Figure 2(a)). OGD/R induced oxidative stress, and the LDH level was used to assess cell death. ECG treatment significantly inhibited LDH leakage induced by OGD (P < 0.01) (Figure 2(b)). As shown in Figure 2(c), OGD/R upregulated intracellular MDA levels compared with control which was significantly decreased by ECG treatment (Figure 2(c)). As MDA was considered an indicator of lipid peroxidation, ECG may show inhibition of lipid peroxidation in HBMVECs that underwent OGD/R. In the OGD/R group, the SOD activities were significantly decreased compared with the control group (Figure 2(d)). ECG treatment significantly increased SOD activity (P < 0.01). Reference: Oxid Med Cell Longev. 2019 Mar 6;2019:7824684. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30962864/
In vivo activity:
The acetic acid-induced writhing and hot plate models in mice were utilized to determine the analgesic effect of epicatechin gallate (ECG) isolated from Bauhinia hookeri. The anti-inflammatory activity of ECG was determined using carrageenan-induced paw edema model. The pro-inflammatory mediators (PGE2 , TNF-α, IL-1β, and IL-6) were estimated in the plasma of different treatment groups. ECG was tested at doses of 100, 200, and 400 mg/kg p.o. and diclofenac sodium was used as a standard drug (100 mg/kg) in all experiments. ECG significantly (p < .001) suppressed the writhing response in mice. The inhibition percentages were 32, 52, and 62%, at the tested doses of ECG, respectively as compared to the positive control group receiving acetic acid only. Furthermore, ECG significantly (p < .001) increased the reaction time in hot plate model. The maximum analgesic effect was evident after 120 min. ECG demonstrated a significant anti-inflammatory activity as evidenced by the inhibition of carrageenan-induced paw edema (46, 50, and 58%, at the tested doses, respectively). This effect was persistent all over the experimental period. ECG produced a significant (p < .001) reduction in plasma PGE2 (by 27, 38, and 50%), TNF-α (15, 33, and 41%), IL-1β (17, 25, and 33%), and IL-6 (22, 32, and 43%), at the tested doses, respectively. This study supports the use of ECG as both analgesic and anti-inflammatory agent. Reference: Drug Dev Res. 2018 Jun;79(4):157-164. https://doi.org/10.1002/ddr.21430
Solvent mg/mL mM
Solubility
DMSO 88.0 198.93
Ethanol 88.0 198.93
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 442.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Fu B, Zeng Q, Zhang Z, Qian M, Chen J, Dong W, Li M. Epicatechin Gallate Protects HBMVECs from Ischemia/Reperfusion Injury through Ameliorating Apoptosis and Autophagy and Promoting Neovascularization. Oxid Med Cell Longev. 2019 Mar 6;2019:7824684. doi: 10.1155/2019/7824684. PMID: 30962864; PMCID: PMC6431361.
In vivo protocol:
1. Al-Sayed E, Abdel-Daim MM. Analgesic and anti-inflammatory activities of epicatechin gallate from Bauhinia hookeri. Drug Dev Res. 2018 Jun;79(4):157-164. doi: 10.1002/ddr.21430. Epub 2018 May 6. PMID: 29732583.
  1: Anderson JC, Grounds H, Reeves S, Taylor PW. Improved synthesis of structural   analogues of (-)-epicatechin gallate for modulation of staphylococcal β-lactam resistance. Tetrahedron. 2014 May 27;70(21):3485-3490. PubMed PMID: 24876661; PubMed Central PMCID: PMC4006114.