A simple synthesis of 3-deoxyanthocyanidins and their O-glucosides. Issue 29 (21st July 2016)

• Record Type: Journal Article
• Authors: Al Bittar, Sheiraz; Mora, Nathalie; Loonis, Michèle; Dangles, Olivier
• Is Part Of: Tetrahedron. Volume 72:Issue 29(2016)
• Page Start: 4294
• Page End: 4302
• Publication Date: 2016-07-21
• Subjects: Anthocyanin -- 3-Deoxyanthocyanidin -- Glycoside -- Synthesis -- Sorghum -- Color; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.05.076
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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 β-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-β-d -glucosides resulted in a mixture of the 5-O- and 7-O-regioisomers in low yield. A preliminary study of the 4′-β-d -glucopyranosyloxy-7-hydroxyflavylium and 7-β-d -glucopyranosyloxy-4′-hydroxy-flavylium ions shows that simply changing the glucosidation site can profoundly affect the color intensity and stability. Graphical abstract: