4670-05-7

Basic information

• Product Name: THEAFLAVIN
• Synonyms: THEAFLAVIN;THEAFLAVINE;1,8-bis(3-alpha,5,7-trihydroxy-2-alpha-chromanyl)-5h-benzocyclohepten-5-one;5h-benzocyclohepten-5-one,1,8-bis(3-alpha,5,7-trihydroxy-2-alpha-chromanyl)-3,;6-trihydroxy-;Theaflavins;6,8,9-trihydroxy-3,11-bis[(2S,3R)-3,5,7-trihydroxychroman-2-yl]bicyclo[5.4.0]undeca-1,3,6,8,10-pentaen-5-one;3,4,6-Trihydroxy-1,8-bis(3,4-dihydro-3α,5,7-trihydroxy-2H-1-benzopyran-2α-yl)-5H-benzocycloheptene-5-one
• CAS NO: 4670-05-7
• Molecular Formula: C₂₉H₂₄O₁₂
• Molecular Weight: 516.5
• Product Categories: Miscellaneous Natural Products
• Mol File: 4670-05-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: 237-240 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 1003.9°Cat760mmHg
• Flash Point: 336.5°C
• Appearance: /
• Density: 1.87g/cm³
• Storage Temp.: -20°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.65±0.20(Predicted)
• CAS DataBase Reference: THEAFLAVIN(CAS DataBase Reference)
• NIST Chemistry Reference: THEAFLAVIN(4670-05-7)
• EPA Substance Registry System: THEAFLAVIN(4670-05-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 4670-05-7(Hazardous Substances Data)

Usage

Description

Theaflavins are a group of polyphenol pigments found in both black and oolong teas. They are obtained by the oxidation and dimerization of green tea catechins during the manufacture of black tea and oolong tea. Theaflavins contribute to the characteristic bright orange-red color of black tea. Theaflavins include theaflavin, theaflavin-3-gallate, theaflavin-3'-gallate and theaflavin-3,3'-digallate.Theaflavins are used to manage cholesterol and used to support the heart and digestive system. They could be used as protective agents against cardiovascular disease and cancer. It is also believed that they have a wide range of other pharmaceutical benefits, including antihypertensive, antioxidative and hypolipidemic activities. It is suggested that theaflavins have a potential to be developed as a safe and affordable topical microbicide for preventing sexual transmission of HIV.

Chemical Properties

red to brown powder

Uses

Theaflavin is a polyphenolic compound found in black tea. Theaflavin derivatives show anti-HIV-1 activity by targeting gp41. Theaflavin is a potent inhibitor of amyloid-β (Aβ) and α-synuclein (αS) fibrillogenesis. Theaflavin also shows potent anti-tumor and and antoxidant activities.

Definition

ChEBI: Theaflavin is a biflavonoid that is 3,4,5-trihydroxybenzocyclohepten-6-one which is substituted at positions 1 and 8 by (2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl groups. It is the main red pigment in black tea. It has a role as an antioxidant, a chelator, a plant metabolite, a radiation protective agent and an antibacterial agent. It is a polyphenol and a biflavonoid.

benefits

Theaflavin is a polyphenolic flavonoid that has been found in black tea and has diverse biological activities, including antineoplastic, antioxidant, anticancer, anti-inflammatory, cholesterol lowering and antiviral properties.

Biological Activity

Theaflavin is a suitable natural inhibitor against influenza A (H1N1) neuraminidase.

References

[1] Lai Kwok Leung, Yalun Su, Ruoyun Chen, Zesheng Zhang, Yu Huang, Zhen-Yu Chen (2001) Theaflavins in Black Tea and Catechins in Green Tea Are Equally Effective, J. Nutr., 131, 2248-2251[2] Yang J, Li L, Tan S, Jin H, Qiu J, Mao Q, Li R, Xia C, Jiang ZH, Jiang S, Liu S (2012) A Natural Theaflavins Preparation Inhibits HIV-1 Infection by Targeting the Entry Step: Potential Applications for Preventing HIV-1 Infection, Fitoterapia, 83, 348-355[3] http://www.xtend-life.com/information/ingredients/theaflavins

Upstream product

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Downstream Products

• 302776-47-2 theanaphthoquinone 

Relevant articles and documents

Accumulation of epigallocatechin quinone dimers during tea fermentation and formation of theasinensins

Production and accumulation of catechin dimer quinones during tea fermentation were chemically confirmed for the first time by trapping as phenazine derivatives. Direct treatment of the fermented tea leaves with o-phenylenediamine yielded five phenazine derivatives (8-12) of o-quinones of an epigallocatechin dimer and its galloyl esters (13-16), in which two flavan units were linked at the B-rings through a C-C bond. Atrop isomerism of the biphenyl bonds was shown to be the R configuration, suggesting that the o-quinone dimers were generated by stereoselective coupling of monomeric quinones. The total concentration of the phenazine derivatives in the o-phenylenediamine-treated tea leaves was higher than that of theaflavins. In contrast, phenazine derivatives of monomeric quinones of epigallocatechin were not isolated. When the fermented tea leaves were heated, the quinone dimers were converted to theasinensins, which are constituents of black tea, suggesting that theasinensins are generated by reduction of the quinone dimers during the heating and drying steps in black tea manufacturing.

CATALYST FOR SYNTHESIZING THEAFLAVINS AND METHOD FOR SYNTHESIZING THEAFLAVINS

The objective/problem addressed by the present invention is to provide a novel technique pertaining to theaflavins synthesis. The present invention pertains to: a theaflavins synthesis catalyst characterized in having a base comprising an inorganic material, and metal nanoparticles anchored to the base, said particles measuring 0.5-100 nm in diameter; and a theaflavins synthesis method in which the catalyst is used.

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.

Oxidation mechanism of black tea pigment theaflavin by peroxidase

A large number of black tea polyphenols remain uncharacterized because of the complexity of catechin oxidation reactions that occur during tea fermentation. In the course of our studies on black tea polyphenols, we examined the enzymatic degradation of theaflavins, which are black tea pigments having a benzotropolone chromophore. Oxidation of theaflavin with peroxidase afforded a new product named theacoumarin A together with known pigment theanaphthoquinone. The structure of the new compound was determined by spectroscopic examination and a production mechanism via theanaphthoquinone is proposed.