Supervisors info:
Γεώργιος Κόκοτος, Καθηγητής, Τμήμα Χημείας, ΕΚΠΑ
Summary:
Royal jelly is a secretion from the hypopharyngeal and mandibular glands of worker bees (Apis mellifera L.). It is a white-yellowish, gelatinous, acidic colloid, containing about 5% fat. Unlike fatty acids of most animal and plant materials, which consist mainly of triglyceride fatty acids each one having 14–20 carbon atoms, royal jelly fatty acids are medium-chained (8–10 carbon atoms) free fatty acids, terminally and/or internally hydroxylated, with terminal mono- or dicarboxylic acid functions, either saturated or monounsaturated at the 2-position.
The predominant fatty acid in royal jelly is trans-10-hydroxy-2-decenoic acid (10-HDA). Apart from thisacid, the most abundant fatty acids in royal jelly are: sebacic acid (decanedioic acid), 2-dodecenedioic acid,10-hydroxydecanoic acid and 3-hydroxy-decanoic acid (3-HDA).
In this thesis, convenient and useful synthetic routes to trans-10-hydroxy-2-decenoic acid and 2-dodecenedioic acid are presented. These routes are based on selective cross-metathesis, using the second generation Hoveyda-Grubbs catalyst. Also, a method for the synthesis of trans-10-hydroxy-2-decenoic acid, based on a Wittig reaction was studied.
Finally, it was important to synthesize deuterated fatty acids containing two deuterium atoms, as such those products may have a variety of applications, both in biosynthesis and degradation studies, and in high resolution mass spectrometry (HRMS) studies as reference compounds.
Keywords:
Royal Jelly, fatty acids, second generation Hoveyda-Grubbs catalyst, deuteration.
