A natural flavonoid
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(−)-Gallocatechin

Item No. 16944

Technical Information
Formal Name
(2S,3R)-3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol
CAS Number
3371-27-5
Synonyms
  • (−)-GC
Molecular Formula
C15H14O7
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 25 mg/mlDMSO: 15 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
210, 269 nm
SMILES
OC1=CC([C@H]2[C@H](O)CC3=C(O)C=C(O)C=C3O2)=CC(O)=C1O
InChi Code
InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m1/s1
InChi Key
XMOCLSLCDHWDHP-DOMZBBRYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    Product Description

    (−)-Gallocatechin ((−)-GC) is an epimer of (−)-epigallocatechin ((−)-EGC; Item No. 11809). They are flavan-3-ols and members of the catechin family of polyphenolic antioxidants found in green tea and other plant extracts.1 Both (−)-GC and (−)-EGC are potent antioxidants and significantly inhibit the proliferation of HCT116 and SW480 cancer cells.2,3,1 (−)-GC also inhibits the aggregation of amyloid β peptide in vitro (IC50 = 17.5 µM).4 With increasing temperature, the steaming of green tea leaves results in the reduction of 2,3-cis isomers, like (−)-EGC, and an increase in 2,3-trans isomers, like (−)-GC.3,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Du, G.J., Zhang, Z., Wen, X.D., et alEpigallocatechin gallate (EGCG) is the most effective cancer chemopreventive polyphenol in green tea. Nutrients 4(11), 1679-1691 (2012).

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

    3. Nomizu, K., Hashida, K., Makino, R., et alAntioxidants from steamed used tea leaves and their reaction behavior. Biosci. Biotechnol. Biochem. 72(7), 1682-1689 (2008).

    4. Xie, H., Wang, J.R., Yau, L.F., et alCatechins and procyanidins of Ginkgo biloba show potent activities towards the inhibition of β-amyloid peptide aggregation and destabilization of preformed fibrils. Molecules 19(4), 5119-5134 (2014).

    5. Timmel, M.A., Byl, J.A.W., and Osheroff, N. Epimerization of green tea catechins during brewing does not affect the ability to poison human type II topoisomerases. Chem. Res. Toxicol. 26(4), 622-628 (2013).