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(−)-Gallocatechin

Item № 16944
CAS № 3371-27-5
Purity ≥98%
product image
                (CAS 3371-27-5)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $25.00 0.00
     5 mg $75.00 0.00
     10 mg $138.00 0.00
     25 mg $281.00 0.00

Pricing updated 2019-06-15. Prices are subject to change without notice.

Description
Synonyms
  • (−)-GC

(−)-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

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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
306.3
Purity
≥98%
Formulation
A crystalline solid
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

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Du, G.J., Zhang, Z., Wen, X.D., et al. Epigallocatechin 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 al. Comparison of antioxidant activity and bioavailability of tea epicatechins with their epimers British Journal of Nutrition 91(6), 873-881 (2004).

3. Nomizu, K., Hashida, K., Makino, R., et al. Antioxidants from steamed used tea leaves and their reaction behavior Bioscience, Biotechnology, and Biochemistry 72(7), 1682-1689 (2008).

4. Xie, H., Wang, J.R., Yau, L.F., et al. Catechins 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 Chemical Research in Toxicology 26(4), 622-628 (2013).

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