A polyphenol flavonoid with diverse biological activities
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(−)-Epicatechin

Item No. 11807

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2R-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3R,5,7-triol
CAS Number
490-46-0
Synonyms
  • epi-Catechin
  • NSC 81161
Molecular Formula
C15H14O6
Formula Weight
290.3
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 12.5 mg/mlDMSO: 12.5 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
λmax
278 nm
SMILES
OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C(O)=C3)O2)C(O)=C1
InChi Code
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
InChi Key
PFTAWBLQPZVEMU-UKRRQHHQSA-N
Origin
Plant/Acacia catechu
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    25 mg

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    Product Description

    (−)-Epicatechin is a polyketide synthase-derived polyphenol flavonoid that has been found in T. cacao and has diverse biological activities.1,2,3,4,5 It scavenges DPPH (Item No. 14805) radicals in a cell-free assay when used at a concentration of 5 µM.2 (−)-Epicatechin inhibits COX-1 (IC50 = 3.2 μM).6 It acts synergistically with epigallocatechin gallate (Item No. 70935) to induce apoptosis in, and reduce the proliferation of, PC-9 lung cancer cells when used at a concentration of 200 µM.4 (−)-Epicatechin (80 mg/kg) reduces LPS-induced increases in plasma creatinine and urea levels in a rat model of renal inflammation.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tauchen, J., Huml, L., Rimpelova, S., et al. Flavonoids and related members of the aromatic polyketide group in human health and disease: Do they really work? Molecules 25(17), 3846 (2020).

    2. Xu, J.Z., Yeung, S.Y.V., Chang, Q., et al. Comparison of antioxidant activity and bioavailability of tea epicatechins with their epimers. Br. J. Nutr. 91(6), 873-881 (2004).

    3. Waffo-Téguo, P., Hawthorne, M.E., Cuendet, M., et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr. Cancer 40(2), 173-179 (2001).

    4. Suganuma, M., Okabe, S., Kai, Y., et al. Synergistic effects of (−)-epigallocatechin gallate with (−)-epicatechin, sulindac, or tamoxifen on cancer-preventive activity in the human lung cancer cell line PC-9. Cancer Res. 59(1), 44-47 (1999).

    5. Prince, P.D., Fischerman, L., Toblli, J.E., et al. LPS-induced renal inflammation is prevented by (−)‐epicatechin in rats. Redox Biol. 11, 342-349 (2017).

    6. Waffo-Téguo, P., Hawthorne, M.E., Cuendet, M., et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr. Cancer 40(2), 173-179 (2001).