302776-47-2

Basic information

• Product Name: theanaphthoquinone
• Synonyms: theanaphthoquinone
• CAS NO: 302776-47-2
• Molecular Weight: 534.476
• Mol File: 302776-47-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: theanaphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: theanaphthoquinone(302776-47-2)
• EPA Substance Registry System: theanaphthoquinone(302776-47-2)

Safety Data

• Hazardous Substances Data: 302776-47-2(Hazardous Substances Data)

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 
• 4670-05-7 theaflavin 

Relevant articles and documents

Stability of black tea polyphenol, theaflavin, and identification of theanaphthoquinone as its major radical reaction product

In the current study, we have focused on isolation and detection of major radical oxidation products from theaflavin in order to better understand antioxidation mechanisms of this compound. Theanaphthoquinone was identified as a major oxidation product of theaflavin from two different oxidant model systems: DPPH and peroxidase/hydrogen peroxide. This result indicated that the benzotropolone moiety in theaflavin may play an important role in its antioxidant properties. The stability of theaflavin was studied in varying pH solutions: simulated gastric juice and buffer solutions of pH 5.5, pH 7.4, and pH 8.5. The results indicated that theaflavin is unstable in alkaline conditions, while it was stable in acidic conditions. Theanaphthoquinone was identified as an autoxidation product of theaflavin during its stability study in alkaline conditions.

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.

Theanaphthoquinone, a novel pigment oxidatively derived from theaflavin during tea-fermentation

Treatment of a mixture of epicatechin and epigallocatechin with extracts of fresh tea leaf or banana fruit generated a new pigment named theanaphthoquinone, which has a 1,2-naphthoquinone moiety oxidatively derived from the benzotropolone unit of theaflavin.