Supervisors info:
Γεώργιος Κόκοτος, Καθηγητής, Τμήμα Χημείας, Εθνικό και Καποδιστριακό Πανεπιστήμιο Αθηνών
Summary:
Fatty acids are essential components of the main lipid classes (triacylgycerols, phospholipids etc), however exhibiting biological roles and activities by their own right, such as lipid mediators in inflammatory conditions. Since fatty acids are widespread in nature and are basic components of foods and natural products, research on their role as bioactive nutrients and their impact on human health is an ever expanding field.
Saturated fatty acids carrying functional groups, like a hydroxyl or a keto (oxo) functionality, have attracted limited attention so far. An unexplored up to date class of naturally occurring fatty acids is that of keto (oxo) fatty acids (KFAs). Although 3-keto fatty acids are found as minor components in animal tissues and are generally intermediates in β-oxidation, little is known about the origin of a range of naturally occurring minor keto fatty acids, differing in chain length and the positions of the keto group.
Upon a thorough search in literature, it became apparent that scarce examples for the synthesis of KFAs exist, which cannot provide a general approach for the synthesis of most key members of KFAs. The aim of the present study was the development of a general efficient method for the synthesis of KFAs and related compounds, such as hydroxy fatty acids (HFAs). Easy access to such compounds would allow an extended study of their bioactivities. A fast, green, reliable, one-step and photochemical process was developed for the synthesis of a library of keto fatty acids. As a key step for the formation of the ketone group, we chose the application of a new photochemical hydroacylation protocol. This green photochemical hydroacylation reaction is carried out under mild reaction conditions on water as the solvent, employing cheap household lamps as the irradiation source, and phenylglyoxylic acid, a cheap, organic, and commercially available compound, as the photoinitiator.
Keywords:
green reaction, hydroacylation, hydroxy fatty acids, keto fatty acids, photochemistry
