Improved Synthesis of Analogues of Red Wine Pyranoanthocyanin Pigments

Author(s)

da Silva, Cassio Pacheco ^[1] ; Pioli, Renan Moraes ^[1] ; Liu, Liu ^{[2, 1]} ; Zheng, Shasha ^{[2, 1]} ; Zhang, Mengjiao ^{[2, 1, 3]} ; de Medeiros Silva, Gustavo Thalmer ^[1] ; Teixeira Carneiro, Vania Maria ^[4] ; Quina, Frank H. ^[1]

Affiliation

^[1] Univ Sao Paulo, Inst Quim, Av Lineu Prestes 748, Cidade Univ, BR-05508000 Sao Paulo - Brazil

^[2] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072 - Peoples R China

^[3] Natl Inst Biol Sci, 7 Sci Pk Rd, Zhongguancun Life Sci Pk, Beijing 102206 - Peoples R China

^[4] Univ Fed Vicosa, Dept Quim, Av Peter Henry Rolfs S-N Campus Univ, BR-36570900 Vicosa, MG - Brazil

• Document type: Journal article
• Source: ACS OMEGA; v. 3, n. 1, p. 954-960, JAN 2018.
• Web of Science Citations: 7

Abstract

An improved procedure is described for the preparation of pyranoflavylium cations from the reaction of 5,7-dihydroxy-4-methyl-flavylium cation with aromatic aldehydes. Modifications of the procedure of Chassaing et al. (Tetrahedron Lett. 2008, 49, 6999-7004; Tetrahedron 2015, 71, 3066-3078) circumvent the reported restriction to electron-rich benzaldehydes and provide access to a wide variety of substituted pyranoflavylium cations, including those with electron-withdrawing substituents or an attached heterocyclic or polycyclic aromatic ring. This opens the way for studies of substituent and structural effects on the ground and excited states of these pyranoanthocyanin analogues, the behavior of which should mirror fundamental aspects of the chemistry and photophysics of the pyranoanthocyanin chromophores present in mature red wines. (AU)

• FAPESP's process: 15/08539-1 - Multi-User Equipment approved in grant 2014/15962-5: ion trap mass spectrometer modified to perform infrared vibrational spectroscopy (IRMPD)
• Grantee: Thiago Carita Correra
• Support Opportunities: Multi-user Equipment Program