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(+)-GALLOCATECHIN

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(+)-GALLOCATECHIN Basic information

Product Name:
(+)-GALLOCATECHIN
Synonyms:
  • 2α-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3β,5,7-triol
  • (2S)-2β-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3α,5,7-triol
  • (2S)-3,4-Dihydro-2β-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3α,5,7-triol
  • (2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
  • 2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-, (2R-trans-)
  • Nsc674038
  • (+)-GALLOCATECHIN
  • (2R,3S)-2-(3,4,5-trihydroxyphenyl)chroman-3,5,7-triol
CAS:
970-73-0
MF:
C15H14O7
MW:
306.27
Product Categories:
  • Flavonoids
Mol File:
970-73-0.mol
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(+)-GALLOCATECHIN Chemical Properties

storage temp. 
Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility 
DMSO (Slightly, Sonicated), Ethanol (Slightly, Sonicated), Methanol (Slightly)
Boiling point:
685.6±55.0 °C(Predicted)
Density 
1.695±0.06 g/cm3(Predicted)
Melting point:
218 °C(Solv: water (7732-18-5))
pka
9.02±0.15(Predicted)
form 
Solid
color 
White to Pale Brown
Stability:
Hygroscopic
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(+)-GALLOCATECHIN Usage And Synthesis

Description

(+)-Gallocatechin is a polyphenol and flavonoid that has been isolated from the leaves of tea plants and has diverse biological activities. It inhibits the adherence of P. gingivalis onto human buccal epithelial cells by more than 50% when used at a concentration of 250 μg/ml. (+)-Gallocatechin has antimutagenic properties in UV-irradiated E. coli cells. It inhibits cell death induced by D-galactosamine and TNF-α in primary cultured mouse hepatocytes by 29.9% when used at a concentration of 80 μM. (+)-Gallocatechin (100 μM) inhibits HCT116 colorectal cancer cell proliferation by 57%.

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from green tea.

Uses

(+)-Gallocatechin is antioxidant isomer of (-)-Gallocatechin (G188990), a potential cancer chemopreventive agent that inhibits the growth and adherence of P. gingivalis onto the buccal epithelial cells. An epimer of (-)-Epigallocatechin (E588940).

Definition

ChEBI: A gallocatechin that has (2R,3S)-configuration. It is found in green tea and bananas.

target

BACE

References

[1] GUANG-JIAN DU. Epigallocatechin Gallate (EGCG) is the most effective cancer chemopreventive polyphenol in green tea.[J]. Nutrients, 2012, 4 11: 1679-1691. DOI: 10.3390/nu4111679
[2] TOMOAKI MATSUO. Identification of (+)-gallocatechin as a bio-antimutagenic compound in Psidium guava leaves[J]. Phytochemistry, 1994, 36 4: Pages 1027-1029. DOI: 10.1016/s0031-9422(00)90484-9
[3] Q XIONG. Hepatoprotective effect of Apocynum venetum and its active constituents.[J]. Planta medica, 2000, 66 2: 127-133. DOI: 10.1055/s-2000-11135
[4] S SAKANAKA. Inhibitory effects of green tea polyphenols on growth and cellular adherence of an oral bacterium, Porphyromonas gingivalis.[J]. Bioscience, Biotechnology, and Biochemistry, 1996, 60 5: 745-749. DOI: 10.1271/bbb.60.745

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