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Abstract:

Cinnamic acids are present in all kinds of plant tissues and hence in herbs and derived medicines, cosmetics and foods. The interest in their role in plants and their therapeutic applications has grown exponentially. Because of their molecular structure they can exist in E- and Z-forms, which are both found in plants. However, since only the E-forms are commercially available, very few in vitro and in vivo studies of the Z-form have been reported. In this work the physico-chemical properties of Z-cinnamic acids in solution have been examined by means of UV-absorption spectroscopy and high-level quantum mechanical computations. For each isomer similar absorption spectra were obtained in methanol and acetonitrile. However, distinct trends were found for Z- and E forms of cinnamic acids in water, where a higher hypsochromic shift of the Z-isomer relative to the E-form was observed. In general the wavelength of maximal absorption of the Z-form is dramatically blue shifted (-30 to -40 nm) to λ < 280 nm, while a slightly blue shift of the absorption maxima for the corresponding E-form (+3 to -4 nm) was observed. This difference is associated with the non-planar, largely distorted, Z-structure and to the almost complete flat structure of the E-form. The results provide a basis for the study of functional and biotechnological roles of cinnamic acids and for the analysis of samples containing mixture of both geometric isomers. © 2015 Published by Elsevier B.V.

Registro:

Documento: Artículo
Título:Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics
Autor:Salum, M.L.; Arroyo Mañez, P.; Luque, F.J.; Erra-Balsells, R.
Filiación:CIHIDECAR-Departamento de Química Orgánica, FCEN, Universidad de Buenos Aires, Pabellón II, 3er P, Buenos Aires, 1428, Argentina
Departamento de Química Orgánica and UMYMFOR (CONICET-UBA), FCEN, Universidad de Buenos Aires, Pabellón II, 3er P, Buenos Aires, 1428, Argentina
Departament de Fisicoquímica, Facultat de Farmacia and Institut de Biomedicina (IBUB), Universitat de Barcelona, Barcelona, E-08028, Spain
Palabras clave:acetonitrile; cinnamic acid derivative; methanol; water; cinnamic acid; cinnamic acid derivative; solution and solubility; water; absorption; Article; chemical structure; isomer; physical chemistry; priority journal; quantum mechanics; ultraviolet spectroscopy; chemical model; chemistry; conformation; infrared spectrophotometry; pH; solution and solubility; stereoisomerism; Cinnamates; Hydrogen-Ion Concentration; Models, Chemical; Molecular Conformation; Solutions; Spectrophotometry, Infrared; Stereoisomerism; Water
Año:2015
Volumen:148
Página de inicio:128
Página de fin:135
DOI: http://dx.doi.org/10.1016/j.jphotobiol.2015.03.032
Título revista:Journal of Photochemistry and Photobiology B: Biology
Título revista abreviado:J. Photochem. Photobiol. B Biol.
ISSN:10111344
CODEN:JPPBE
CAS:acetonitrile, 75-05-8; methanol, 67-56-1; water, 7732-18-5; cinnamic acid, 4151-45-5, 538-42-1, 621-82-9; Cinnamates; cinnamic acid; Solutions; Water
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10111344_v148_n_p128_Salum

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Citas:

---------- APA ----------
Salum, M.L., Arroyo Mañez, P., Luque, F.J. & Erra-Balsells, R. (2015) . Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics. Journal of Photochemistry and Photobiology B: Biology, 148, 128-135.
http://dx.doi.org/10.1016/j.jphotobiol.2015.03.032
---------- CHICAGO ----------
Salum, M.L., Arroyo Mañez, P., Luque, F.J., Erra-Balsells, R. "Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics" . Journal of Photochemistry and Photobiology B: Biology 148 (2015) : 128-135.
http://dx.doi.org/10.1016/j.jphotobiol.2015.03.032
---------- MLA ----------
Salum, M.L., Arroyo Mañez, P., Luque, F.J., Erra-Balsells, R. "Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics" . Journal of Photochemistry and Photobiology B: Biology, vol. 148, 2015, pp. 128-135.
http://dx.doi.org/10.1016/j.jphotobiol.2015.03.032
---------- VANCOUVER ----------
Salum, M.L., Arroyo Mañez, P., Luque, F.J., Erra-Balsells, R. Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics. J. Photochem. Photobiol. B Biol. 2015;148:128-135.
http://dx.doi.org/10.1016/j.jphotobiol.2015.03.032