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Synlett 2016; 27(17): 2459-2462
DOI: 10.1055/s-0035-1562471
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Structural Characterization of Amino-Based Pyranoanthocyanins with Extended Electronic Delocalization

Joana Oliveira*
REQUIMTE, Laboratório Associado para a Química Verde, Departamento de Química e Bioquímica, Faculdade de Ciências, Universid ade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal   Email: jsoliveira@fc.up.pt
,
Paula Araújo
REQUIMTE, Laboratório Associado para a Química Verde, Departamento de Química e Bioquímica, Faculdade de Ciências, Universid ade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal   Email: jsoliveira@fc.up.pt
,
Ana Fernandes
REQUIMTE, Laboratório Associado para a Química Verde, Departamento de Química e Bioquímica, Faculdade de Ciências, Universid ade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal   Email: jsoliveira@fc.up.pt
,
Nuno Mateus
REQUIMTE, Laboratório Associado para a Química Verde, Departamento de Química e Bioquímica, Faculdade de Ciências, Universid ade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal   Email: jsoliveira@fc.up.pt
,
Victor de Freitas
REQUIMTE, Laboratório Associado para a Química Verde, Departamento de Química e Bioquímica, Faculdade de Ciências, Universid ade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal   Email: jsoliveira@fc.up.pt
› Author Affiliations
Further Information

Publication History

Received: 02 May 2016

Accepted after revision: 17 June 2016

Publication Date:
25 July 2016 (online)

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Abstract

Two new pyranoanthocyanin amino derivatives with extended electronic delocalization were obtained from the reaction of methyl­pyranomalvidin-3-O-glucoside with two amino-derived cinnamaldehydes, 4-(dimethylamino)- and 4-(diethylamino)-cinnamaldehyde. Structural characterization revealed the presence of a butadienylidene linkage connecting the pyranoanthocyanin and the cinnamyl moieties. The unexpected red color presented by the new molecules is due to the presence of a dicationic form of the pigments at acidic pH as confirmed by ESI–MS.

Key words

pyranoanthocyanin - amino derivatives - extended electronic delocalization - butadienylidene linkage - dicationic form

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562471.
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  • References and Notes

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