AIM OF THE STUDY
The aim of this study is the molecular characterization of the products obtained from the ozonization of olive and sunflower oils by establishing the exact molecular mass of the major components of both oils using high resolution mass spectrometry (QTof). The main aim of the study is to find the derivatives obtained from the two major components of both oils, oleic and linoleic acid. Additionally, derivatives of the trioleines were also found in these oils.
METHOD OF STRUCTURAL ELUCIDATION
Composition of raw materials was elucidated by comparison of the theoretical composition of olive and sunflower oil found in the literature with the data acquired in the infusion experiments. The chemical structures found in raw materials were used to predict possible products of the ozonolysis reaction based on the mechanism published by Gabin et.al.1 Also other possible outcomes of the oxidation of methyl oleates suggested by Curtis et. al.2
Ozonolysis of trioleines in finger marks exposed to ambient conditions have been recently described by Frick et. al.3 Using high resolution mass spectrometry to characterize some of the products. These results have been used to predict the structures found in the samples analyzed.
Ozonides are also another group of compounds that can be produced during the ozonolysis process, although they are highly unstable undergoing a cleavage to afford the corresponding aldehydes and carboxylic acids in as little as 16 h as demonstrated in the NMR studies conducted by Tortini et. al.4
The exact molecular masses of the proposed structures were calculated using the software Chemdraw professional final Version. The theoretical exact masses were used to support the proposed chemical structure.
The molecular structures presented in this section have been proposed by extrapolation of the reaction mechanism and in agreement with the exact molecular mass observed in the spectrum.
Two ozonized samples with different degrees of ozonization are analyzed to establish how the degree of ozonization affects the chemical composition of the final product. In addition, the starting materials of the ozonolysis are also analyzed to assist interpretation of the data acquired.
Chemical structures are proposed based on observed exact masses by taking intoaccount the ozonolysis reaction mechanism and the composition of the starting materials.
In the present study 9-oxononanoic acid and azelaic acid were found in ozonized oils as cleavage products of linoleic and oleic acid judging by the high resolution mass spectrum of ozonized olive and sunflower oil samples.
Azelaic acid is present in whole grains like wheat, rye, barley and oat seeds. Previous studies published by Saravanan et. al.5 suggests that this chemical can be beneficial to increase activity of key liver enzymes that help to restore levels of glucose, as revealed in their experiments with diabetic mice. Analogous experiments have been conducted by Natake et. al.6 with 9-oxononanoic, finding a reduction on lipogenesis in rat liver. Also the benefits of azelaic acid as a cosmetic have been reported by many authors.7
Additionally, many derivatives of triacylglycerols were proposed as products of the ozonolysis reaction. These derivatives are formed from the cleavage of the double bonds present in the triacylglycerols to give the corresponding aldehydes and carboxylic acids. The reaction results in a complex mixture of different triacylglycerol derivatives. These kinds of products have been reported before in ambient ozonolysis of fingerprints3 but to the best of our knowledge have not been reported in ozonized oils.
“I have read this report and confirm that to the best of my knowledge it accurately describes the conduct and results of the study. All information included in this Study Report has been carefully examined and reviewed in compliance with the protocol and SOPs, and has been found to be accurate, complete and scientifically valid.”
CEO and Biologist of KeyBiological
Member of the Spanish Society of Ozone Therapy –SEOT
1) M. F. Díaz, J. A. Gavin, J. Braz. Chem. Soc. 2007, 8, 513-518.
2) C. Sun, Y. Zhao, J. M. Curtis, Rapid Commun. Mass Spectrom. 2012, 26, 921-930
3) A. A. Frick, N. Kummer, A. Moraleda, C. Weyermann, Analyst 2020, 145, 4212-4223
4) M. Cirlini, A. Caligiani, G. Palla, A. Ascentiis, P. Tortini, Ozone: Science & engineering
2012, 34, 293-299
5) S. Muthulakshmi, R. Saravanan, Biochimie 2013, 95, 1239-1244
6) S. Minamoto, K. Kanazawa, H. Ashida, M. Natake Biochimica et Biophysica Acta 1988, 958 199-204
7) Fitton, A., Goa, K.L. Drugs 1991, 41, 780–798