A polyphenol with diverse biological activities
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(−)-Catechin Gallate

Item No. 24963

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,4,5-trihydroxy-benzoic acid, (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester
CAS Number
130405-40-2
Synonyms
  • (–)-CG
Molecular Formula
C22H18O10
Formula Weight
442.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlPBS (pH 7.2): 0.3 mg/ml
λmax
280 nm
SMILES
OC1=CC([C@H]2[C@H](OC(C3=CC(O)=C(O)C(O)=C3)=O)CC4=C(O)C=C(O)C=C4O2)=CC=C1O
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
InChi Key
LSHVYAFMTMFKBA-CTNGQTDRSA-N
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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    Product Description

    (–)-Catechin gallate ((–)-CG) is a catechin polyphenol that has been found in green tea extracts with diverse biological activities.1,2,3,4 It inhibits proliferation of MDA-MB-231 breast cancer cells and reduces VEGF-induced tyrosine phosphorylation of VEGF receptor 2 (VEGFR2) in bovine aortic endothelial cells (BAECs) in a concentration-dependent manner.1,2 (–)-CG is a competitive inhibitor of the facilitative glucose transporter GLUT4 (Ki = 90 μM) and inhibits methylglucose uptake by isolated rat adipocytes (IC50 = 50 μM).3 It is also lytic against T. cruzi amastigotes, with a 50% bactericidal concentration (MBC50) value of 48 pM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lamy, S., Gingras, D., and Béliveau, R. Green tea catechins inhibit vascular endothelial growth factor receptor phosphorylation. Cancer Res. 62(2), 381-385 (2002).

    2. Sartippour, M.R., Heber, D., Ma, J., et al. Green tea and its catechins inhibit breast cancer xenografts. Nutr. Cancer 40(2), 149-156 (2001).

    3. Strobel, P., Allard, C., Perez-Acle, T., et al. Myricetin, quercetin and catechin-gallate inhibit glucose uptake in isolated rat adipocytes. Biochem. J. 386(Pt 3), 471-478 (2005).

    4. Paveto, C., Güida, M.C., Esteva, M.I., et al. Anti-Trypanosoma cruzi activity of green tea (Camellia sinensis) catechins. Antimicrob. Agents Chemother. 48(1), 69-74 (2004).