UV irradiation of trans-resveratrol leads to its photochemical isomerization and electrocyclization, giving rise to different byproducts. Preliminary attempts to purify and characterize these products were in the majority of cases unsuccessful. In the present work, the resveratrol photoreaction products were analyzed by HPLC, and one of these compounds, 2,4,6-trihydroxyphenanthrene (THP), was purified and unambiguously identified. The structure of THP was unequivocally characterized for the first time by combined GC–MS, ESI-MS/MS, NMR, and FT-IR analyses.
Isolation and Identification of 2,4,6-Trihydroxyphenanthrene as a Byproduct of trans-Resveratrol Photochemical Isomerization and Electrocyclization / Francioso, Antonio; Boffi, Alberto; Villani, Claudio; L., Manzi; D'Erme, Maria; Macone, Alberto; Mosca, Luciana. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - (2014), p. 140918114504002. [10.1021/jo501405m]
Isolation and Identification of 2,4,6-Trihydroxyphenanthrene as a Byproduct of trans-Resveratrol Photochemical Isomerization and Electrocyclization
FRANCIOSO, ANTONIO;BOFFI, Alberto;VILLANI, Claudio;D'ERME, Maria;MACONE, ALBERTO;MOSCA, Luciana
2014
Abstract
UV irradiation of trans-resveratrol leads to its photochemical isomerization and electrocyclization, giving rise to different byproducts. Preliminary attempts to purify and characterize these products were in the majority of cases unsuccessful. In the present work, the resveratrol photoreaction products were analyzed by HPLC, and one of these compounds, 2,4,6-trihydroxyphenanthrene (THP), was purified and unambiguously identified. The structure of THP was unequivocally characterized for the first time by combined GC–MS, ESI-MS/MS, NMR, and FT-IR analyses.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
