Home
Resources
Publications
Efficient Synthesis of Theaflavin 3-Gallate by a Tyrosinase-Catalyzed Reaction With (-)-Epicatechin and (-)-Epigallocatechin Gallate in a 1-Octanol/Buffer Biphasic System

Efficient Synthesis of Theaflavin 3-Gallate by a Tyrosinase-Catalyzed Reaction With (-)-Epicatechin and (-)-Epigallocatechin Gallate in a 1-Octanol/Buffer Biphasic System

Asako Narai-Kanayama, Yoshinori Uekusa, Fumiyuki Kiuchi, Tsutomu Nakayama

J Agric Food Chem. 2018 Dec 26;66(51):13464-13472.

PMID: 30482011

Abstract:

Theaflavins, the orange-red pigments contained in black tea, have attracted attention as a result of their health-promoting effects. However, their synthetic preparation, in which the enzymatic oxidation of catechol-type catechin is followed by the quinone-induced oxidative dimerization of selectively combined catechol- and pyrogallol-type catechins, provides only a low yield. In the present study, we found that a 1-octanol/buffer biphasic system improved the yield of theaflavin 3-gallate in a tyrosinase-catalyzed synthetic reaction with (-)-epicatechin and (-)-epigallocatechin gallate. When the enzymatic reaction proceeded in a buffer solution, oxidized (-)-epigallocatechin gallate was preferentially used for self-dimerization. However, self-dimerization was suppressed in the octanol phase, allowing oxidized (-)-epigallocatechin gallate to participate in coupling with (-)-epicatechin quinone, leading to effective production of theaflavin 3-gallate. Furthermore, the preferential localization of theaflavin 3-gallate in the octanol phase prevented (-)-epicatechin-quinone-induced degradation.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP30462341	Theaflavin 3-gallate		30462-34-1	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: