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

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 and is known for its antioxidant, chelator, plant metabolite, radiation protective, and antibacterial properties. Theaflavin is a polyphenolic compound found in black tea, with derivatives showing anti-HIV-1 activity, potent inhibition of amyloid-β (Aβ) and α-synuclein (αS) fibrillogenesis, and exhibiting anti-tumor and antioxidant activities.

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

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

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.