Theaflavin 3,3'-digallate

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-alpha, IL-1beta, and IL-6, expression of JNK and p38, and nuclear translocation of NF-kappaB in RAW 264.7 cells. In vivo, TFDG reduces serum levels of TNF-alpha, IL-1beta, 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.Formal Name: 3,4,5-trihydroxy-benzoic acid, 1,1'-[(3,4,6-trihydroxy-5-oxo-5H-benzocycloheptene-1,8-diyl)bis[(2R,3R)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-2,3-diyl]] ester. CAS Number: 30462-35-2. Synonyms: TF3, TFDG. Molecular Formula: C43H32O20. Formula Weight: 868.7. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 25 mg/ml, DMF:PBS (pH 7.2) (1:6): 0.14 mg/ml, DMSO: 10 mg/ml, Ethanol: 10 mg/ml. lambdamax: 278, 377 nm. SMILES: O=C1C2=C(O)C(O)=CC([C@@H]3[C@H](OC(C4=CC(O)=C(O)C(O)=C4)=O)CC(C(O)=CC(O)=C5)=C5O3)=C2C=C([C@H]6OC(C=C(O)C=C7O)=C7C[C@H]6OC(C8=CC(O)=C(O)C(O)=C8)=O)C=C1O. InChi Code: InChI=1S/C43H32O20/c44-17-7-23(46)21-12-33(62-42(58)15-3-25(48)36(54)26(49)4-15)40(60-31(21)9-17)14-1-19-20(11-30(53)39(57)35(19)38(56)29(52)2-14)41-34(13-22-24(47)8-18(45)10-32(22)61-41)63-43(59)16-5-27(50)37(55)28(51)6-16/h1-11,33-34,40-41,44-51,53-55,57H,12-13H2,(H,52,56)/t33-,34-,40-,41-/m1/s1. InChi Key: ZEASWHWETFMWCV-ISBUVJFSSA-N. Origin: Plant/Black Tea.