Synthesis of a new bluish pigment from the reaction of a methylpyranoanthocyanin with sinapaldehyde

Tetrahedron Letters

Volumn 52, Issue 16, 2011, Pages 1996-2000

  Oliveira, Joana ^a   Mateus, Nuno ^a   Freitas, Victor De ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Bluish color; Charge transfer reaction; Methylpyranoanthocyanins; pKa; Sinapaldehyde; UV visible spectroscopy

Indexed keywords

ANTHOCYANOSIDE DERIVATIVE; CHEMICAL COMPOUND; METHYLPYRANOMALVIDIN 3 GLUCOSIDE; PIGMENT; SINAPALDEHYDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLOR; IONIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PH; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 79952737164     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.079     Document Type: Article

References (31)

1. Francia-Aricha, E. M.; Guerra, M. T.; Rivas-Gonzalo, J. C.; Santos-Buelga, C. J. Agric. Food. Chem. 1997, 45, 2262-2266.
2. Liao, H.; Cai, Y.; Haslam, E. J. Sci. Food Agric. 1992, 59, 299-305.
3. Rivas-Gonzalo, J. C.; Bravo-Haro, S.; Santos-Buelga, C. J. Agric. Food. Chem. 1995, 43, 1444-1449.
4. Somers, T. C. Phytochemistry 1971, 10, 2175-2186.
5. Timberlake, C. F.; Bridle, P. Am. J. Enol. Vitic. 1976, 27, 97-105.
6. Bakker, J.; Timberlake, C. F. J. Agric. Food. Chem. 1997, 45, 35-43.
7. He, J.; Santos-Buelga, C.; Silva, A. M. S.; Mateus, N.; De Freitas, V. J. Agric. Food. Chem. 2006, 54, 9598-9603.
8. Fulcrand, H.; dos Santos, P. J. C.; Sarni-Manchado, P.; Cheynier, V.; Favre-Bonvin, J. J. Chem. Soc., Perkin Trans. 1 1996, 735-739.
9. Rentzsch, M.; Schwarz, M.; Winterhalter, P.; Hermosin-Gutierrez, I. J. Agric. Food. Chem. 2007, 55, 4883-4888.
10. Schwarz, M.; Wabnitz, T. C.; Winterhalter, P. J. Agric. Food. Chem. 2003, 51, 3682-3687.
11. Fulcrand, H.; Benabdeljalil, C.; Rigaud, J.; Cheynier, V.; Moutounet, M. Phytochemistry 1998, 47, 1401-1407.
12. Hayasaka, Y.; Asenstorfer, R. E. J. Agric. Food. Chem. 2002, 50, 756-761.
13. Schwarz, M.; Jerz, G.; Winterhalter, P. Vitis 2003, 42, 105-106.
14. Mateus, N.; Silva, A. M. S.; Rivas-Gonzalo, J. C.; Santos-Buelga, C.; de Freitas, V. J. Agric. Food. Chem. 2003, 51, 1919-1923.
15. Oliveira, J.; de Freitas, V.; Silva, A. M. S.; Mateus, N. J. Agric. Food. Chem. 2007, 55, 6349-6356.
16. Oliveira, J.; Azevedo, J.; Silva, A. M. S.; Teixeira, N. r.; Cruz, L.; Mateus, N.; de Freitas, V. J. Agric. Food. Chem. 2010, 58, 5154-5159.
17. Nave, F.; Teixeira, N.; Mateus, N.; de Freitas, V. Rapid Commun. Mass Spectrom. 2010, 24, 1964-1970.
18. Bax, A.; Subramanian, S. J. Magn. Reson. 1986, 67, 565-569.
19. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093-2094.
20. Oliveira, J.; de Freitas, V.; Mateus, N. Tetrahedron Lett. 2009, 50, 3933-3935.
21. Oliveira, J.; Fernandes, V.; Miranda, C.; Santos-Buelga, C.; Silva, A.; de Freitas, V.; Mateus, N. J. Agric. Food. Chem. 2006, 54, 6894-6903.
22. Oliveira, J.; Petrov, V.; Parola, A. J.; Pina, F.; Azevedo, J.; Teixeira, N.; Bras, N. F.; Fernandes, P. A.; Mateus, N.; Ramos, M. J.; de Freitas, V. J. Phys. Chem. B 2011. doi:10.1021/jp110593.
23. Chassaing, S.; Isorez, G.; Kueny-Stotz, M.; Brouillard, R. Tetrahedron Lett. 2008, 49, 6999-7004.
24. Küster, F. W.; Thiel, A. In Tabelle per le Analisi Chimiche e Chimico-Fisiche; Hoepli: Milano, Italy, 1982; pp 157-160.
25. Gans, P.; Sabatini, A.; Vacca, A. Anal. Chim. 1999, 89, 45-49.
26. Brouillard, R.; Dubois, J. E. J. Am. Chem. Soc. 1977, 99, 1359-1364.
27. Nave, F.; Petrov, V.; Pina, F.; Teixeira, N. r.; Mateus, N.; de Freitas, V. J. Phys. Chem. B 2010, 114, 13487-13496.
28. Santos, H.; Turner, D. L.; Lima, J. C.; Figueiredo, P.; Pina, F. S.; Maçanita, A. n. L. Phytochemistry 1993, 33, 1227-1232.
29. Cruz, L.; Petrov, V.; Teixeira, N.; Mateus, N.; Pina, F.; de Freitas, V. J. Phys. Chem. B 2010, 114, 13232-13240.
30. Oliveira, J.; Mateus, N.; Silva, A. M. S.; de Freitas, V. J. Phys. Chem. B 2009, 113, 11352-11358.
31. Timberlake, C. F. J. Chem. Soc. 1957, 4987-4993.