Theaflavin digallate; Theaflavine-3,3'-digallate

Base Information

• Chemical Name: Theaflavin digallate; Theaflavine-3,3'-digallate
• CAS No.: 30462-35-2
• Molecular Formula: C43H32O20
• Molecular Weight: 868.715
• Hs Code.: 29329990
• Mol file: 30462-35-2.mol

Synonyms:Theaflavin digallate; Theaflavine-3,3'-digallate;[(2R,3R)-2-[1-[(2S,3S)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-3,4,6-trihydroxy-5-oxobenzo[7]annulen-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate

Chemical Property of Theaflavin digallate; Theaflavine-3,3'-digallate

Chemical Property:

• Melting Point: 226～230℃
• Boiling Point: 1352.64 °C at 760 mmHg
• PKA: 6.55±0.20(Predicted)
• Flash Point: 411.033 °C
• PSA: 351.12000
• Density: 1.978 g/cm³
• LogP: 4.17640
• XLogP3: 3
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 8
• Exact Mass: 868.14869341
• Heavy Atom Count: 63
• Complexity: 1950

Purity/Quality:

98% ^*data from raw suppliers

8-Gingerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C(=CC(=C4O)O)C5C(CC6=C(C=C(C=C6O5)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)O)O)O
• 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. Theaflavin 3,3''-Digallate has been found to be an inhibitor against human pancreatic α-Amylase.

Technology Process of Theaflavin digallate; Theaflavine-3,3'-digallate

There total 2 articles about Theaflavin digallate; Theaflavine-3,3'-digallate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 10.0%

(-)-epicatechin gallate (863-03-6,10517-25-6,13445-34-6,17431-25-3,20819-16-3,25615-05-8,130405-40-2,1257-08-5) + (-)-epigallocathechin gallate (2596-50-1,4233-96-9,5127-64-0,19065-20-4,107965-88-8,137766-94-0,989-51-5) → theaflavin-3,3'-di-o-gallate (30462-35-2)

Guidance literature:

With polyphenol oxidase; In aq. phosphate buffer; for 2h; pH=6; Reagent/catalyst; Enzymatic reaction;

DOI:10.1016/j.tetlet.2014.07.092

Reference yield:

→ theaflavin-3,3'-di-o-gallate (30462-35-2)

Guidance literature:

DOI:10.1016/S0040-4020(01)99386-X

Reference yield: 3.13%

theaflavin-3,3'-di-o-gallate (30462-35-2) → (5R,6R)-2-Carboxymethyl-6-{4-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxy-benzoyloxy)-chroman-2-yl]-1,2,8-trihydroxy-9-oxo-9H-benzocyclohepten-6-yl}-5-(3,4,5-trihydroxy-benzoyloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid + (5R,6R)-2-Carboxymethyl-6-{8-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxy-benzoyloxy)-chroman-2-yl]-3,4,6-trihydroxy-5-oxo-5H-benzocyclohepten-1-yl}-5-(3,4,5-trihydroxy-benzoyloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid

Guidance literature:

With dihydrogen peroxide; In water; acetone; at 20 ℃; for 48h;

DOI:10.1016/S0040-4039(03)01382-0

upstream raw materials:

(-)-epicatechin gallate

(-)-epigallocathechin gallate

Refernces

• 1、 Takemoto, Masumi,Takemoto, Hiroaki,Sakurada, Asuka. "Synthesis of theaflavins with Camellia sinensis cell culture and inhibition of increase in blood sugar values in high-fat diet mice subjected to sucrose or glucose loading". . p. 5038 - 5040. Retrieved 2015/02/02.
• 2、 Sang, Shengmin,Lambert, Joshua D.,Tian, Shiying,Hong, Jungil,Hou, Zhe,Ryu, Jae-He,Stark, Ruth E.,Rosen, Robert T.,Huang, Mou-Tuan,Yang, Chung S.,Ho, Chi-Tang. "Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities". . p. 459 - 467. Retrieved 2007/10/03.