Synthesis, characterization, thermal behavior, and biological activity of ozonides from vegetable oils

Kogawa, Nathália Rodrigues de Almeida; Arruda, Eduardo José de; Micheletti, Ana Camila; Matos, Maria de Fátima Cepa; Oliveira, Lincoln Carlos Silva de; Lima, Dênis Pires de; Carvalho, Nádia Cristina Pereira; Oliveira, Paola Dias de; Cunha, Marillin de Castro; Ojeda, Mariáh; Beatriz, Adilson

doi:10.1039/c5ra02798e

Cited by 28 publications

(30 citation statements)

References 45 publications

(83 reference statements)

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“…It is interesting to underline that many authors correlate the antimicrobial activity of ozonated oils to the peroxide index (PI), believing that activity is greater when PI is higher. However, many investigations have demonstrated that an increase in PI does not affect oil activity [20,78], probably because the antimicrobial mechanism of ozonated vegetable oils is related to oxidizing species, as reported by some authors [19,41].…”

Section: Topical Applications Of Ozonated Oilsmentioning

confidence: 91%

“…High viscosity and gel-like appearance have been found in the product (oleogel) obtained from the ozonation of sunflower oil in the presence of water, whereas the oleogel that was generated without this polar solvent did not display these features [41]. Some bibliographic references that indicate values obtained from the characterization of several ozonated oils are reported, as examples, in Table 1.…”

Section: Viscositymentioning

confidence: 99%

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Ozonated Oils as Antimicrobial Systems in Topical Applications. Their Characterization, Current Applications, and Advances in Improved Delivery Techniques

Ugazio

Tullio²,

Binello

et al. 2020

Molecules

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The search for a wide spectrum of antimicrobial agents that can avoid resistance while maintaining reasonable side effects has led to ozonated oils experiencing an increase in scientific interest and clinical applications. The treatment of vegetable oils with ozone leads to the creation of a reservoir of ozone that slowly releases into the skin thanks to the fact that ozone can be held as ozonides of unsaturated fatty acids. Interest in the use of ozonated oils has meant that several ozonated-vegetable-oil-containing products have been commercialized as cosmetic and pharmaceutical agents, and in innovative textile products with antibacterial activity. New approaches to the delivery of ozonated oils have very recently appeared in an attempt to improve their characteristics and reduce drawbacks, such as an unpleasant odor, high viscosity and undesired effects on skin, including irritation and rashes. The present review focuses on the current status of delivery agents that use ozonated oils as antimicrobial agents in topical (dermal, skin, and soft tissues) treatments. Challenges and future opportunities for these delivery systems will also be discussed.

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Section: Topical Applications Of Ozonated Oilsmentioning

confidence: 91%

Section: Viscositymentioning

confidence: 99%

Ozonated Oils as Antimicrobial Systems in Topical Applications. Their Characterization, Current Applications, and Advances in Improved Delivery Techniques

Ugazio

Tullio²,

Binello

et al. 2020

Molecules

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“…The most interesting of these products is OTOA, the ozonide of oleic acid triglyceride, which is the major triglyceride (>45%) in olive oil. OTOA, which is non-toxic, biocompatible and a biodegradable material [33,34], could be a promising additive for introduction into the PLA matrix via electrospinning.…”

Section: Introductionmentioning

confidence: 99%

Effect of Glycero-(9,10-trioxolane)-trialeate on the Physicochemical Properties of Non-Woven Polylactic Acid Fiber Materials

et al. 2021

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Biocompatible glycero (9,10-trioxolane) trioleate (ozonide of oleic acid triglyceride, OTOA) was incorporated into polylactic acid (PLA) fibers by electrospinning and nonwoven PLA mats with 1%, 3% and 5% OTOA content. The morphological, mechanical, thermal and water sorption properties of electrospun PLA mats after the addition of OTOA were studied. A morphological analysis showed that the addition of OTOA increased the average fiber diameter and induced the formation of pores on the fiber surface, leading to an increase in the specific surface area for OTOA-modified PLA fibrous mats. PLA fiber mats with 3% OTOA content were characterized by a highly porous surface morphology, an increased specific surface area and high-water sorption. Differential scanning calorimetry (DSC) was used to analyze the thermal properties of the fibrous PLA mats. The glass transition temperatures of the fibers from the PLA–OTOA composites decreased as the OTOA content increased, which was attributed to the plasticizing effect of OTOA. DSC results showed that OTOA aided the PLA amorphization process, thus reducing the crystallinity of the obtained nonwoven PLA–OTOA materials. An analysis of the mechanical properties showed that the tensile strength of electrospun PLA mats was improved by the addition of OTOA. Additionally, fibrous PLA mats with 3% OTOA content showed increased elasticity compared to the pristine PLA material. The obtained porous PLA electrospun fibers with the optimal 3% OTOA content have the potential for various biomedical applications such as drug delivery and in tissue engineering.

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“…Various methods are used for studying the characterisation of ozonated vegetable oils e.g. 1 H and 13 C NMR, FT-IR, GC, determination of peroxide and acidity values and viscosity measurements (Soriano et al, 2003;Sega et al, 2010;Diaz et al, 2005, Rodrigues de Almeida Kogawa et al, 2015.…”

Section: Introductionmentioning

confidence: 99%

Chemical and structural variations in hazelnut and soybean oils after ozone treatments

et al. 2018

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SUMMARY:In the present work, the effect of ozone treatments on the structural properties of soybean oil (SBO) and hazelnut oil (HO) were investigated. The study presents the findings and results about the oxidation of HO and SBO with ozone, which has not been fully studied previously. The HO and SBO were treated with ozone gas for 1, 5, 15, 30, 60, 180 and 360 min. The ozone reactivity with the SBO and HO during the ozone treatment was analyzed by 1 H, 13 C NMR, FTIR and GC. The iodine value, viscosity and color variables (L*, a* and b*) of untreated and ozone treated oils were determined. Reaction products were identified according to the Criegee mechanism. New signals at 5.15 and 104.35 ppm were assigned to the ring protons of 1,2,4-trioxolane (secondary ozonide) in the ozonated oils in 1 H and 13 C NMR, respectively. Ozonated oils exhibited peaks at 9.75 and 2.43 ppm in 1 H and NMR, which corresponded to the aldehydic proton and α-methylene group and to the carbonyl carbon, respectively. The peak at 43.9 ppm in 13 C NMR was related to the α-methylene group and to the carbonyl carbon. The new signals formed in the ozonation process gradually increased with respect to ozone treatment time. After 360 min of ozone treatment, the carbon-carbon double bond signal, which belongs to the unsaturated fatty acids, disappeared completely in the spectrum. An increase in viscosity, a decrease in iodine value and a dramatic reduction in b* of the oil samples on (+) axis were observed with increased ozone treatment time. KEYWORDS: FTIR; GC; Hazelnut oil; NMR; Ozone; Soybean oil; Viscosity RESUMEN:Variaciones químicas y estructurales de aceites de avellana y soja después de tratamientos con ozono. En el presente trabajo se investigó el efecto de tratamientos con ozono sobre las propiedades estructurales de aceites de soja (SBO) y avellana (HO). El estudio muestra hallazgos y resultados sobre la oxidación de HO y SBO con ozono que no se habían presentado previamente. Los aceites HO y SBO son tratados con ozono gaseoso durante 1, 5, 15, 30, 60, 180 y 360 min. La reactividad del ozono con SBO y HO durante el tratamiento se analizó mediante 1 H, 13 C NMR, FTIR y GC. Se midieron las variables: índice de yodo, viscosidad y color (L *, a * y b *) de los aceites no tratados y tratados con ozono. Los productos de reacción se identificaron de acuerdo con el mecanismo de Criegee. Se asignaron nuevas señales a 5,15 y 104,35 ppm a los anillos protónicos de 1,2,4-trioxolano (ozónido secundario) en aceites ozonizados en 1 H y 13 C RMN, respectivamente. Los aceites ozonizados también mostraron picos a 9,75 y 2,43 ppm en 1 H NMR correspondientes al protón aldehídico y al grupo α-metileno, respectivamente. El pico a 43,9 ppm en 13 C RMN se relacionó con el C carbonilo del grupo α-metileno. Las nuevas señales formadas en el proceso de ozonización aumentaron gradualmente con respecto al tiempo de tratamiento con ozono. Después de un tratamiento de 360 minutos con ozono, la señal del doble enlace C=C que pertenece a los ácidos grasos insaturados ...

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Synthesis, characterization, thermal behavior, and biological activity of ozonides from vegetable oils

Cited by 28 publications

References 45 publications

Ozonated Oils as Antimicrobial Systems in Topical Applications. Their Characterization, Current Applications, and Advances in Improved Delivery Techniques

Ozonated Oils as Antimicrobial Systems in Topical Applications. Their Characterization, Current Applications, and Advances in Improved Delivery Techniques

Effect of Glycero-(9,10-trioxolane)-trialeate on the Physicochemical Properties of Non-Woven Polylactic Acid Fiber Materials

Chemical and structural variations in hazelnut and soybean oils after ozone treatments

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