Journal of Chemical Software
Online ISSN : 1883-8359
Print ISSN : 0918-0761
ISSN-L : 0918-0761
How to Increase the Reactivity of Hydroxylmethylation of Tea Catechins?–A Theoretical Study of the Introduction of a Galloyl Moiety at C-3 Position–
Katsuhiro TAMURATakatoshi MATSUMOTOUmpei NAGASHIMA
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2001 Volume 7 Issue 2 Pages 57-64

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Abstract

Tea catechins and related compounds, (-)-Epicatechin gallate and (-)-Epigallocatechin ga llate, which have a galloyl moiety at the C-3 position (see Figure 1), show higher reactivity of hyd roxylmethylation than others. We performed theoretical calculations on 5 tea catechins by the semi-e mpirical molecular orbital method.
It is found that introduction of a galloyl moiety makes HOMO localize at the C-6 and C-8 positions. These variations of orbital energies lead to a high reactivi ty. It is suggested that the introduction of functional groups that have a large -electron system in to tea catechins raises the reactivity of hydroxylmethylation.

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© 2001 by the Chemical Software Society of Japan
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