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

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

Uses

Used in Pharmaceutical Applications:
THEAFLAVIN is used as an anti-HIV-1 agent for targeting gp41, potentially serving as a safe and affordable topical microbicide for preventing sexual transmission of HIV.
Used in Neurodegenerative Disease Management:
THEAFLAVIN is used as an inhibitor for amyloid-β (Aβ) and α-synuclein (αS) fibrillogenesis, which are associated with neurodegenerative diseases such as Alzheimer's and Parkinson's.
Used in Anticancer Applications:
THEAFLAVIN is used as an anti-tumor agent, contributing to the prevention and treatment of cancer.
Used in Cardiovascular Disease Prevention:
THEAFLAVIN is used as a protective agent against cardiovascular disease due to its antioxidant and hypolipidemic activities.
Used in Digestive Health:
THEAFLAVIN is used to support the digestive system, potentially aiding in the management of digestive health.
Used in Cholesterol Management:
THEAFLAVIN is used to manage cholesterol levels, contributing to overall heart health.
Used in Antioxidant Applications:
THEAFLAVIN is used as an antioxidant, providing protection against oxidative stress and related health issues.
Used in Bacterial Infections:
THEAFLAVIN is used as an antibacterial agent, potentially treating and preventing bacterial infections.
Used in Radiation Protection:
THEAFLAVIN is used as a radiation protective agent, offering potential benefits for individuals exposed to radiation.
Used in the Tea Industry:
THEAFLAVIN is used as a pigment for giving black tea its characteristic bright orange-red color.

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

• 122440-41-9 4-(3,4-dihydro-3α,5,7-trihydroxy-2H-1-benzopyran-2α-yl)-1,2-benzoquinone 
• 970-73-0 epigallocatechin 
• 1203550-44-0 (2R,3R)-5,7,5,7-tetra-O-(2-nitrobenzenesulfonyl)neotheaflavin 
• 154-23-4 catechin 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 1203550-46-2 (2R,3R)-5,7,5,7-tetra-O-(2-nitrobenzenesulfonyl)theaflavin 
• 95-54-5 1,2-diamino-benzene 
• 70-18-8 GLUTATHIONE 

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.

Structures of two new oxidation products of green tea polyphenols generated by model tea fermentation

To clarify the oxidation mechanism of green tea catechins during tea fermentation, pure catechins were oxidized with a catechin-free homogenate of tea leaf. Oxidation of a mixture of (-)-epicatechin and (-)-epigallocatechin yielded a new metabolite, named dehydrotheaflavin, produced by the oxidation of a benzotropolone moiety of the black tea pigment theaflavin. Similar oxidation of a mixture of (-)-epicatechin and (-)-epigallocatechin 3-O-gallate afforded a new dimer of (-)-epigallocatechin 3-O-gallate, which was generated by the oxidation and cycloaddition of two pyrogallol rings. Structures were determined by spectroscopic method, and the oxidation mechanisms for the formation of the products were proposed.

Nonenzymatic Biomimetic Synthesis of Black Tea Pigment Theaflavins

Theaflavins are reddish-orange black tea pigments with a benzotropolone chromophore, and their various biological activities have been reported. Theaflavins are produced by oxidative coupling between catechol-type and pyrogallol-type catechins via bicyclo[3.2.1]octane-type intermediates. In this study, a new method for nonenzymatic biomimetic synthesis of theaflavins was developed using the DPPH radical as an oxidizing agent.

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.

Syntheses of methylated catechins and theaflavins using 2-nitrobenzenesulfonyl group to protect and deactivate phenol

An efficient and versatile synthetic method for labile polyphenols was established using 2-nitrobenzenesulfonate (Ns) as a protecting group for phenol. This methodology provides regio-and stereoselective access to a range of methylated catechins, such as methylated epigallocatechin gallates, that are not readily available from natural sources. In addition, biomimetic synthesis of theaflavins from catechins was accomplished using Ns protection to minimize undesired side reactions of electron-rich aromatic rings during oxidation, enabling construction of the complex benzotropolone core in a single-step oxidative coupling reaction. Availability of these compounds will aid detailed structure-biological activity relationship studies of catechins.

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.

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

Theaflavin and its galloyl esters are major polyphenolic pigments of black tea. We compared the efficiency of a variety of oxidizing enzyme systems to synthesize theaflavin and its galloyl esters. Camellia sinensis cell culture efficiently synthesized theaflavin from epicatechin and epigallocatechin with 70% yield and 100% conversion in 4 min. In an administration experiment performed in mice, theaflavin inhibited the increase blood glucose levels in mice that were fed a high-fat diet and subjected to glucose or sucrose loading in mice.

Synthesis of Theaflavins via Biomimetic Oxidative Coupling Reactions

Biomimetic synthesis of theaflavins from catechins was accomplished by using 2-nitrobenzenesulfonyl (Ns) as a protecting group for phenols to minimize undesired side reactions of the electron-rich aromatic rings. This enabled the construction of the complex benzotropolone core in a single-step oxidative coupling reaction. Georg Thieme Verlag Stuttgart · New York.

Reaction of the black tea pigment theaflavin during enzymatic oxidation of tea catechins

Degradation of the black tea pigment theaflavin was examined in detail. Enzymatic oxidation of a mixture of epigallocatechin and epicatechin initially produced theaflavin, while prolonged reaction decreased the product. Addition of ethanol to the reaction mixture at the point when theaflavin began to decrease afforded four new products, together with theanaphthoquinone, a known oxidation product of theaflavin. The structures of the new products were determined by spectroscopic methods. One of the products was an ethanol adduct of a theanaphthoquinone precursor, and this reacted with theaflavin to give two further products. A product generated by coupling of theaflavin with epicatechin quinone was also obtained. The structures of the products indicate that oxidation and coupling with quinones are key reactions in the degradation of theaflavins. The degradation of theaflavin probably contributes to production of thearubigins.