30462-35-2

Basic information

• Product Name: 8-Gingerol
• Synonyms: 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;theaflavin 3;THEAFLAVIN 3,3'-DIGALLATE;THEAFLAVIN 3,3'-DI-O-GALLATE;8-GINGEROL, HPLC 98%;8-Gingerol;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
• CAS NO: 30462-35-2
• Molecular Formula: C₄₃H₃₂O₂₀
• Molecular Weight: 868.7
• Product Categories: Miscellaneous Natural Products;The group of Ginerols;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 30462-35-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 226～230℃
• Boiling Point: 1352.64 °C at 760 mmHg
• Flash Point: 411.033 °C
• Appearance: /
• Density: 1.978 g/cm³
• PKA: 6.55±0.20(Predicted)
• CAS DataBase Reference: 8-Gingerol(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Gingerol(30462-35-2)
• EPA Substance Registry System: 8-Gingerol(30462-35-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 30462-35-2(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 30462-35-2 differently. You can refer to the following data:
1. 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.
2. Theaflavin 3,3''-Digallate has been found to be an inhibitor against human pancreatic α-Amylase.

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): δH 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.

Upstream product

• 863-03-6 (-)-epicatechin gallate 
• 2596-50-1 (-)-epigallocathechin gallate 

Relevant articles and documents

Specificity of tyrosinase-catalyzed synthesis of theaflavins

This study kinetically characterized the mechanism of the enzymatic synthesis of theaflavins (TFs) from catechins by mushroom tyrosinase (EC 1.14.18.1). In reactions containing one of four catechins, (-)-epicatechin (EC), (-)-epigallocatechin (EGC), and their galloylated forms (ECg and EGCg), they were oxidized by tyrosinase with apparent KM values of 3.78, 5.55, 0.80, and 3.05 mM, respectively, and with different consumption rates, of which EC was more than four times higher than those of the others. In reactions with binary combinations of catechins with tyrosinase, the synthesis of TF1 from EC and EGC occurred most efficiently, while the yields of mono- and di-galloylated TFs, TF2A, TF2B, and TF3, were low. Time-dependent changes in concentrations of the reactants suggested that the enzymatic oxidation of catechins and the subsequent non-enzymatic coupling redox reaction between the quinone derived from EC or ECg and the intact pyrogallol-type catechin (EGC or EGCg) proceeded concurrently. The latter reaction induced the rapid decrease of EGC and EGCg and it was remarkable for EGCg. So the efficiency of condensation of a pair of quinones from catechol- and pyrogallol-type catechins is restricted, critically influencing the yield of TFs. Using green tea extracts as mixtures of the four substrate catechins, tyrosinase produced TF1 most abundantly. Furthermore, a remarkable enhancement of production of TF2A and TF2B as well as TF1 was observed, when the initial concentration of EGCg was low. These results suggest that the catechin composition has an impact on yields of TFs.

Benzotropolone derivatives and modulation of inflammatory response

The present invention provides novel benzotropolone derivatives represented by the general formula: 1 including neotheaflavate B and EGCGCa. The benzotropolone derivatives of the present invention are effective antioxidant and anti-inflammatory agents. The present invention also provides novel method of synthesizing benzotropolone compounds in high yields and method of treating inflammatory conditions using benzotropolone containing compounds.