Theaflavin 3,3′-digallate

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Theaflavin 3,3′-digallate

Biological Activities

Product Name: Theaflavin 3,3′-digallate
CAS No.: 30462-35-2
Chemical Name: Theaflavin 3,3′-digallate
Synonyms: TFDG;theaflavin 3;8-Gingerol Hplc;8-GINGEROL, HPLC 98%;Theaflavin 3,3’THEAFLAVIN 3,3'-DIGALLATE;THEAFLAVIN 3,3'-DI-O-GALLATE;Theaflavin-3,3-digallate(TF3);Theaflavin 3,3'-digallate USP/EP/BP;3,4,6-Trihydroxy-1,8-bis[[(2R)-3,4-dihydro-5,7-dihydroxy-3α-(3,4,5-trihydroxybenzoyloxy)-2H-1-benzopyran]-2α-yl]-5H-benzocycloheptene-5-one
CBNumber: CB0156596
Molecular Formula: C43H32O20
Formula Weight: 868.71
MOL File: 30462-35-2.mol

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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)
pka: 6.55±0.20(Predicted)
color: Red-purple
InChIKey: ZEASWHWETFMWCV-ISBUVJFSSA-N
CAS DataBase Reference: 30462-35-2

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Safety

WGK Germany: 3
HS Code: 29329990

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PHL83344
Product name: Theaflavin 3,3′-digallate
Purity: phyproof? Reference Substance
Packaging: 10mg
Price: $618
Updated: 2024/03/01

Sigma-Aldrich

Product number: 92223
Product name: Theaflavin 3,3′-digallate
Purity: analytical standard
Packaging: 1mg
Price: $683
Updated: 2022/05/15

Cayman Chemical

Product number: 25215
Product name: Theaflavin 3,3'-digallate
Purity: ≥98%
Packaging: 1mg
Price: $57
Updated: 2024/03/01

Cayman Chemical

Product number: 25215
Product name: Theaflavin 3,3'-digallate
Purity: ≥98%
Packaging: 5mg
Price: $208
Updated: 2024/03/01

Cayman Chemical

Product number: 25215
Product name: Theaflavin 3,3'-digallate
Purity: ≥98%
Packaging: 10mg
Price: $330
Updated: 2024/03/01

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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

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

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View Lastest Price from Theaflavin 3,3′-digallate manufacturers

Career Henan Chemical Co

Product: 8-Gingerol 30462-35-2
Price: US $100.00/KG
Min. Order: 1KG
Purity: 97%
Supply Ability: customise
Release date: 2018-07-26

30462-35-2, Theaflavin 3,3′-digallateRelated Search:

6-GINGEROL,[6]-GINGEROL, ZINGIBER OFFICINALE Propyl gallate Theaflavin Methyl gallate THEAFLAVIN 3'-O-GALLATE 1,3,6-TRI-O-GALLOYL-B-D-GLUCOSE (-)-Epigallocatechin Punicalagin (-)-EGCG-3''-O-ME 6-Shogaol 8-O-acetyl shanzhiside methyl ester YUNACONITINE lithospermic acid THEAFLAVINE-3-GALLATE THEAFLAVINE-3,3'-DIGALLATE 10-GINGEROL (-)-Epicatechin gallate cis-(±)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

theaflavin 3

THEAFLAVIN 3,3'-DIGALLATE

THEAFLAVIN 3,3'-DI-O-GALLATE

3,4,5-Trihydroxybenzoic acid (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

8-GINGEROL, HPLC 98%

3,4,6-Trihydroxy-1,8-bis[[(2R)-3,4-dihydro-3α-(3,4,5-trihydroxybenzoyloxy)-5,7-dihydroxy-2H-1-benzopyran]-2α-yl]-5H-benzocycloheptene-5-one

3,4,6-Trihydroxy-1,8-bis[[(2R)-3,4-dihydro-5,7-dihydroxy-3α-(3,4,5-trihydroxybenzoyloxy)-2H-1-benzopyran]-2α-yl]-5H-benzocycloheptene-5-one

8-Gingerol Hplc

[(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

Theaflavin-3,3-digallate(TF3)

TFDG

Theaflavin 3,3&rsquo

Benzoic acid, 3,4,5-trihydroxy-, 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

Theaflavin 3,3'-digallate USP/EP/BP

TheaflAVin-3-3’-digallateQ: What is TheaflAVin-3-3’-digallate Q: What is the CAS Number of TheaflAVin-3-3’-digallate Q: What is the storage condition of TheaflAVin-3-3’-digallate Q: What are the applications of TheaflAVin-3-3’-digallate

[(2R,3R)-3-[1-[5,7-dihydroxy-2-(3,4,5-trihydroxybenzoyl)oxy-chroman-3-yl]-3,4,6-trihydroxy-5-oxo-benzo[7]annulen-8-yl]-5,7-dihydroxy-chroman-2-yl] 3,4,5-trihydroxybenzoate

30462-35-2

C43H32O20

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract

The group of Ginerols

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