Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics
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 bo...
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paper:paper_10111344_v148_n_p128_Salum2023-06-08T15:59:39Z Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics Arroyo Mañez, Pau Erra Balsells, Rosa 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 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. Fil:Arroyo Mañez, P. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Erra-Balsells, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2015 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10111344_v148_n_p128_Salum http://hdl.handle.net/20.500.12110/paper_10111344_v148_n_p128_Salum |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Arroyo Mañez, Pau Erra Balsells, Rosa Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics |
| topic_facet |
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 |
| description |
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. |
| author |
Arroyo Mañez, Pau Erra Balsells, Rosa |
| author_facet |
Arroyo Mañez, Pau Erra Balsells, Rosa |
| author_sort |
Arroyo Mañez, Pau |
| title |
Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics |
| title_short |
Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics |
| title_full |
Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics |
| title_fullStr |
Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics |
| title_full_unstemmed |
Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: The peculiarity of Z-cinnamics |
| title_sort |
combined experimental and computational investigation of the absorption spectra of e- and z-cinnamic acids in solution: the peculiarity of z-cinnamics |
| publishDate |
2015 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10111344_v148_n_p128_Salum http://hdl.handle.net/20.500.12110/paper_10111344_v148_n_p128_Salum |
| work_keys_str_mv |
AT arroyomanezpau combinedexperimentalandcomputationalinvestigationoftheabsorptionspectraofeandzcinnamicacidsinsolutionthepeculiarityofzcinnamics AT errabalsellsrosa combinedexperimentalandcomputationalinvestigationoftheabsorptionspectraofeandzcinnamicacidsinsolutionthepeculiarityofzcinnamics |
| _version_ |
1768544001788477440 |