Theaflavin 3,3'-di-O-gallate

Modify Date: 2024-01-03 20:13:37

Theaflavin 3,3'-di-O-gallate Structure
Theaflavin 3,3'-di-O-gallate structure
Common Name Theaflavin 3,3'-di-O-gallate
CAS Number 30462-35-2 Molecular Weight 868.702
Density 2.0±0.1 g/cm3 Boiling Point 1324.7±65.0 °C at 760 mmHg
Molecular Formula C43H32O20 Melting Point 226-230℃
MSDS USA Flash Point 402.9±27.8 °C

 Use of Theaflavin 3,3'-di-O-gallate


Theaflavin 3,3'-digallate (TF3), the typical pigment in black tea, is a good antitumor agent. Theaflavin 3,3'-digallate is generally regarded as the effective component for the inhibitory effects against carcinogenesis without adverse side effects by affecting multiple signal transduction pathways, such as upregulating p53 and p21, inhibiting phosphorylation of the cell survival protein Akt and MAPK pathway, downregulation of NF-κB, shifting the ratio between pro-/antiapoptotic proteins. Theaflavin 3,3'-digallate causes a rapid and sustained decrease in phospho-ERK1/2 and -MEK1/2 protein expression. Theaflavin 3,3'-digallate inhibits HCT116 cell growth with an IC50 of 17.26 μM[1].

 Names

Name [(2R,3R)-2-[1-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-3,4,5-trihydroxy-6-oxobenzo[7]annulen-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Synonym More Synonyms

 Theaflavin 3,3'-di-O-gallate Biological Activity

Description Theaflavin 3,3'-digallate (TF3), the typical pigment in black tea, is a good antitumor agent. Theaflavin 3,3'-digallate is generally regarded as the effective component for the inhibitory effects against carcinogenesis without adverse side effects by affecting multiple signal transduction pathways, such as upregulating p53 and p21, inhibiting phosphorylation of the cell survival protein Akt and MAPK pathway, downregulation of NF-κB, shifting the ratio between pro-/antiapoptotic proteins. Theaflavin 3,3'-digallate causes a rapid and sustained decrease in phospho-ERK1/2 and -MEK1/2 protein expression. Theaflavin 3,3'-digallate inhibits HCT116 cell growth with an IC50 of 17.26 μM[1].
Related Catalog
Target

Akt

NF-κB

MEK1

MEK2

ERK1

ERK2

References

[1]. Ding Y, et al. Pre-treated theaflavin-3,3'-digallate has a higher inhibitory effect on the HCT116 cell line. Food Nutr Res. 2017 Nov 15;61(1):1400340.

 Chemical & Physical Properties

Density 2.0±0.1 g/cm3
Boiling Point 1324.7±65.0 °C at 760 mmHg
Melting Point 226-230℃
Molecular Formula C43H32O20
Molecular Weight 868.702
Flash Point 402.9±27.8 °C
Exact Mass 868.148682
PSA 351.12000
LogP 3.88
Vapour Pressure 0.0±0.3 mmHg at 25°C
Index of Refraction 1.908

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR NONH for all modes of transport
HS Code 29329990

 Precursor & DownStream

Precursor  2

DownStream  0

 Articles1

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Prostate 75(5) , 550-9, (2015)

Preclinical and epidemiologic studies suggest chemopreventive effects of green tea (GT) and black tea (BT) in prostate cancer. In the current study we determined the effect of GT and BT consumption on...

 Synonyms

8-Gingerol
(3,4,5-Trihydroxy-6-oxo-6H-benzo[7]annulene-1,8-diyl)bis[(2R,3R)-5,7-dihydroxy-3,4-dihydro-2H-chromene-2,3-diyl] bis(3,4,5-trihydroxybenzoate)
theaflavin 3,3'-O-digallate
Theaflavin-3,3'-digallate
theaflavin-3,3'-di-O-gallate
theaflavin 3,3'-gallate
Benzoic acid, 3,4,5-trihydroxy-, (3,4,5-trihydroxy-6-oxo-6H-benzocycloheptene-1,8-diyl)bis[(2R,3R)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-2,3-diyl] ester
Theaflavin digallate
TF-3
Theaflavin 3,3'-digallate
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