30462-34-1

Basic information

• Product Name: THEAFLAVINE-3-GALLATE
• Synonyms: THEAFLAVIN 3-O-GALLATE;THEAFLAVINE-3-GALLATE;THEAFLAVINMONOGALLATES;THEAFLAVINMONOGALLATEA;THEAFLAVIN3GALLATE(3-ISOMER);3,4,6-Trihydroxy-1-[(2S,3S)-3,5,7-trihydroxychroman-2-yl]-8-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)chroman-2-yl]-5H-benzocyclohepten-5-one;Theaflavin 2A;Theaflavin gallate A
• CAS NO: 30462-34-1
• Molecular Formula: C₃₆H₂₈O₁₆
• Molecular Weight: 716.6
• Product Categories: Miscellaneous Natural Products
• Mol File: 30462-34-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 1173.618 °C at 760 mmHg
• Flash Point: 373.16 °C
• Appearance: /
• Density: 1.93
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.893
• Storage Temp.: -20°C
• PKA: 6.65±0.20(Predicted)
• CAS DataBase Reference: THEAFLAVINE-3-GALLATE(CAS DataBase Reference)
• NIST Chemistry Reference: THEAFLAVINE-3-GALLATE(30462-34-1)
• EPA Substance Registry System: THEAFLAVINE-3-GALLATE(30462-34-1)

Safety Data

• Hazardous Substances Data: 30462-34-1(Hazardous Substances Data)

Usage

Description

Theaflavin-3-gallate is a theaflavin derivative, which is abundantly found in black tea and is produced during the fermentation process. It has been studied for its potential as a cancer-fighting chemical when combined with cisplatin, particularly against ovarian cancer cells.

Uses

Used in Pharmaceutical Industry:
Theaflavin-3-gallate is used as an anticancer agent for its potential to combat ovarian cancer cells. It is particularly effective when combined with cisplatin, a chemotherapy drug, enhancing its cancer-fighting properties and targeting ovarian cancer cells more effectively.
Used in Cancer Research:
Theaflavin-3-gallate is used as a subject of study in cancer research to explore its potential as a therapeutic agent against various types of cancer. Its combination with cisplatin is of particular interest, as it may offer new treatment options for patients with ovarian cancer and potentially other cancer types.

Formation

Theaflavin-3-gallate is a crystalline solid.

InChI:InChI=1/C36H28O16/c37-14-5-20(39)18-10-26(45)35(51-27(18)7-14)17-9-25(44)33(48)30-16(17)1-12(2-24(43)32(30)47)34-29(11-19-21(40)6-15(38)8-28(19)50-34)52-36(49)13-3-22(41)31(46)23(42)4-13/h1-9,26,29,34-35,37-42,44-46,48H,10-11H2,(H,43,47)/t26-,29-,34-,35-/m1/s1

Upstream product

• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 2596-50-1 (-)-epigallocathechin gallate 
• 863-03-6 (-)-epicatechin gallate 
• 970-73-0 epigallocatechin 

Relevant articles and documents

Theadibenzotropolone A, a new type pigment from enzymatic oxidation of (-)-epicatechin and (-)-epigallocatechin gallate and characterized from black tea using LC/MS/MS

Theaflavins and thearubigins are major pigments of black tea. In the course of studies on the oxidation mechanism of tea polyphenols, a new type of tea pigment, theadibenzotropolone A, together with theaflavin 3-gallate were formed by the reaction of (-)-epicatechin (EC) and (-)-epigallocatechin gallate (EGCG) with horseradish peroxidase in the presence of H2O2. The structure of theadibenzotropolone A was elucidated on the basis of MS and 2D NMR spectroscopic analyses. The observation that galloyl ester groups of theaflavins can be oxidized to form dibenzotropolone skeletons strongly implied that this type of oxidation as an important pathway to extend the molecular size of thearubigins. The existence of this compound in black tea was characterized by LC/ESI-MS/MS. Theadibenzotropolone A is the first theaflavin type trimer of catechins in black tea.

Efficient Synthesis of Theaflavin 3-Gallate by a Tyrosinase-Catalyzed Reaction with (-)-Epicatechin and (-)-Epigallocatechin Gallate in a 1-Octanol/Buffer Biphasic System

Theaflavins, the orange-red pigments contained in black tea, have attracted attention as a result of their health-promoting effects. However, their synthetic preparation, in which the enzymatic oxidation of catechol-type catechin is followed by the quinon

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.