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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• 1203550-44-0 (2R,3R)-5,7,5,7-tetra-O-(2-nitrobenzenesulfonyl)neotheaflavin 
• 154-23-4 catechin 
• 1203550-46-2 (2R,3R)-5,7,5,7-tetra-O-(2-nitrobenzenesulfonyl)theaflavin 
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• 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.

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.

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.

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.