Biological Activities
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Theaflavin 3,3′-digallate

Biological Activities
Theaflavin 3,3′-digallate Structure
Theaflavin 3,3′-digallate
  • CAS No.30462-35-2
  • Chemical Name:Theaflavin 3,3′-digallate
  • CBNumber:CB0156596
  • Molecular Formula:C43H32O20
  • Formula Weight:868.71
  • MOL File:30462-35-2.mol
Theaflavin 3,3′-digallate Property
  • Melting point 226～230℃
  • Boiling point 1352.6±65.0 °C(Predicted)
  • Density 1.97±0.1 g/cm3(Predicted)
  • storage temp. Store at -20°C, sealed storage, away from moisture and light
  • solubility DMSO : 41.67 mg/mL (47.97 mM; Need ultrasonic)
  • form Solid
  • pka 6.55±0.20(Predicted)
  • color Red-purple
  • InChIKey ZEASWHWETFMWCV-ISBUVJFSSA-N
  • CAS DataBase Reference 30462-35-2
  • FDA UNII LB0IJB138K
  • UNSPSC Code 41116107
  • NACRES NA.24
Safety
  • WGK Germany  :3
  • HS Code  :29329990
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal word
  • Hazard statements
  • Precautionary statements

Theaflavin 3,3′-digallate Chemical Properties,Usage,Production

  • Biological Activities

    Theaflavin-3,3'-digallate (TFDG) is a major polyphenol found in black tea with diverse biological activities. It has antioxidant activity, inhibiting the formation of superoxide radicals, singlet oxygen, hydrogen peroxide, and hydroxyl radicals in vitro (IC50s = 26.7, 0.83, 0.39, and 25.07 µmol/L, respectively).
    It also reduces hydroxyl radical-induced damage to plasmid DNA. TFDG (12.5-50 µM) prevents LPS-induced release of TNF-α, IL-1β, and IL-6, expression of JNK and p38, and nuclear translocation of NF-κB in RAW 264.7 cells [2]. In vivo, TFDG reduces serum levels of TNF-α, IL-1β, and IL-6 and decreases pulmonary edema, pulmonary congestion, and thickening of the alveolar wall in a mouse model of LPS-induced acute lung injury. It also inhibits osteoclast formation, polarization, and osteoclastic bone resorption in vitro and reduces titanium particle-induced bone erosion and the number of mature osteoclasts in mice in a dose-dependent manner. 

  • Description Theaflavin-3,3''-digallate (TFDG) is a major polyphenol found in black tea with diverse biological activities. It has antioxidant activity, inhibiting the formation of superoxide radicals, singlet oxygen, hydrogen peroxide, and hydroxyl radicals in vitro (IC50s = 26.7, 0.83, 0.39, and 25.07 μmol/L, respectively). It also reduces hydroxyl radical-induced damage to plasmid DNA. TFDG (12.5-50 μM) prevents LPS-induced release of TNF-α, IL-1β, and IL-6, expression of JNK and p38, and nuclear translocation of NF-κB in RAW 264.7 cells. In vivo, TFDG reduces serum levels of TNF-α, IL-1β, and IL-6 and decreases pulmonary edema, pulmonary congestion, and thickening of the alveolar wall in a mouse model of LPS-induced acute lung injury. It also inhibits osteoclast formation, polarization, and osteoclastic bone resorption in vitro and reduces titanium particle-induced bone erosion and the number of mature osteoclasts in mice in a dose-dependent manner.
  • Uses Theaflavin 3,3′-digallate may be used as an analytical reference standard for the quantification of the analyte in tea samples using high-performance liquid chromatography with tandem mass spectrometric detection.
  • Uses Theaflavin 3,3''-Digallate has been found to be an inhibitor against human pancreatic α-Amylase.
  • Definition ChEBI: Theaflavin 3,3'-digallate is a catechin.
  • General Description Theaflavin 3,3′-digallate is a theaflavin derivative, exhibiting antioxidative, anti-inflammatory, and anti-tumor activities. It is also associated with many beneficial health effects, including the prevention of cancer and heart disease.
  • Synthesis Synthesis_30462-35-2
    1. Enzymatic Oxidation and Isolation of Theaflavins, EC (1 g, 3.5 mmol) and EGC (1 g, 3.3 mmol) were dissolved into the 200 mL of phosphate-citrate buffer (50 mM, pH 5.0) along with 2 g of crude PPO enzyme. The enzymatic oxidation was carried out at room temperature for 6 hour with stirring. The reaction solution was then subjected to fractionation with the same volume of ethyl acetate with three times. Then, the organic layer was concentrated under reduced pressure. The resulting residues were subjected to Sephadex LH-20 column chromatography eluting with gradient of ethanol to 20% of acetone in ethanol. Among the collected 14 fractions (each c.a. 90 mL), 8-10 fractions were combined, and concentrated under reduced pressure. The resulting residue was subjected to further purification on a RP-18 silica gel column eluting with gradient of 40%~50% of aqueous methanol. During elution, 38 fractions (each c.a. 13 mL) were received. Among them, 10-17 fractions were combined, and concentrated under reduced pressure, and were subjected to freeze-drying. It yielded deep-reddish color of compound 1 (280 mg). Along with the same enzyme reaction and isolation procedure, compound 2 was obtained from EC and EGCG reaction. The enzymatic oxidation of EGC and ECG, ECG and EGCG reaction yielded compound 3 and compound 4, respectively. compound 4, Theaflavin 3,3'-digallate 1H NMR (CD3OD, 600 MHz): |?H 7.79 1H s, 7.76 1H s, 7.47 1H s, 6.88 2H s, 6.80 2H s, 6.07 1H d, J=2.4 Hz, 6.03 2H d, J=2.4 Hz, 6.00 1H d, J=2.4 Hz, 5.86 1H brs, 5.76 1H m, 5.67 1H m, 5.21 1H s, 3.17 1H dd, J=4.8, 16.8 Hz, 3.09 1H dd, J=4.8, 17.4, 2.91 2H m.
Theaflavin 3,3′-digallate Preparation Products And Raw materials
Raw materials
Preparation Products
Theaflavin 3,3′-digallate Suppliers
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