Progress Towards the Synthesis of a Betalain Analogue

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Title: Progress Towards the Synthesis of a Betalain Analogue
Author: Kim, Phillip
Advisor: Newirth, Terry
Department: Haverford College. Department of Chemistry
Type: Thesis (B.S.)
Issue Date: 2010
Abstract: Betalains are responsible for giving beets their characteristic red color and have a unique electrophilic π-bond chromophore. Interest in betalains has increased due to their potential uses as a natural food colorant and their antioxidant properties. Betalains’ sensitivity to pH, heat, oxygen, and light has been extensively documented, but the reactivity of betalains’ electrophilic chromophore with nucleophiles has yet to be explored. Betalains fall into two groups, betacyanins and betaxanthins. Both groups are derived from betalamic acid, which gives them both the conserved π-bond chromophore. Previous work in our lab has shown that betanin reacts with nucleophilic cysteine. To study the effects of a nucleophile on the π-bond chromophore, we propose to synthesize an analogue stripped down to the π-bonded network. This research focuses on advancing and improving a multi-step synthesis of a betalain analogue, which will be observed in the presence of cysteine and its nucleophilic thiol. The current reaction scheme involves six steps. To date, (E/Z)-1-((E/Z)-2-(2,3-dihydropyridin-4(1H)-ylidene)ethylidene)pyrrolidinium-2-carboxylate, the analogue, has been successfully synthesized. However, the analogue is unstable under the current conditions of our synthesis.
Subject: Betalains -- Synthesis
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Kim, Phillip. "Progress Towards the Synthesis of a Betalain Analogue". 2010. Available electronically from

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