4.4 Article

A simple synthesis of 3-deoxyanthocyanidins and their O-glucosides

Journal

TETRAHEDRON
Volume 72, Issue 29, Pages 4294-4302

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.05.076

Keywords

Anthocyanin; 3-Deoxyanthocyanidin; Glycoside; Synthesis; Sorghum; Color

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This work deals with the chemical synthesis of simple analogs of anthocyanins, the main class of water-soluble natural pigments. Flavylium ions with hydroxyl, methoxyl and beta-D-glucopyranosyloxyl substituents at positions 4' and 7 have been prepared by straightforward chemical procedures. Moreover, the two 3-deoxyanthocyanidins of red sorghum apigeninidin (4',5,7-trihydroxyflavylium) and luteolinidin (3',4',5,7-tetrahydroxyflavylium) were synthesized in a one-step protocol. Attempts to synthesize luteolinidin O-beta-D-glucosides resulted in a mixture of the 5-O- and 7-O-regioisomers in low yield. A preliminary study of the 4'-beta-D-glucopyranosyloxy-7-hydroxyflavylium and 7-beta-D-glucopyranosyloxy-4'-hydroxy-flavylium ions shows that simply changing the glucosidation site can profoundly affect the color intensity and stability. (C) 2016 Elsevier Ltd. All rights reserved.

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