Synthesis of 1,2,4 trioxolanes from vegetable oils for pharmaceutical and veterinary application

Abstract

Vegetable oils are rich in mono-and poly-unsaturated fatty acids, and these compounds contain carbon-carbon double bonds available for chemical/structural modification, especially via oxidative processes. Sunflower oil obtained from seed of sunflower (Helianthus annuus) contains a large amount of these acids, such as linoleic (48-74%) and oleic (14-39%) acids, proving to be an ideal starting material for these changes [1]. Ozone is an oxidizing agent that reacts with double bonds of fatty acids present in vegetable oils to form ozonides or 1,2,4 trioxolanes, and peroxidic species such as hydroperoxides, hydrogen peroxide, polymeric peroxides and other organic peroxides. These compounds are of great pharmaceutical interest for the treatment of various dermatological diseases, due to their antimicrobial properties and stimulating action on tissue repair and regeneration [2]. In this work, the sunflower oil was ozonized, and the ideal conditions, as reaction time, ozone concentration and temperature, were determined. The IR and 1H and 13C NMR of ozonized oils confirm the formation of 1,2,4 trioxolane ring according to the mechanism proposed by Criegee [3]. The ozonolysis reaction was performed under different conditions and the product is in the process of knowledge protection or patent.

Keywords

• ozonolysis
• ozonized vegetable oils