Spectroscopic Characterization of Ozonated Sunflower Oil

Díaz, Maritza F.; Sazatornil, José A. Gavín; Ledea, Oscar; Hernández, Fuensanta; Alaiz, Manuel; Garcés, Rafael

doi:10.1080/01919510590945822

Cited by 29 publications

(21 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Also in figure 6 the (Figure 7), we observed that the multiplet at δH 5.3 ppm correlated to the carbon atoms δC 129.7-130.0 ppm, spectral region of methynic carbons near unsaturated carbons. The multiplet δH ϭ 5.1 ppm correlated to the carbon atoms δC 104.2-104.3 ppm, they belong to carbons methynic from ozonides and oligomers, these assignations are similar to those reported from ozonated olive oil (Miura,.2001;Díaz, 2005b). Signal of methylenic carbon at δC 43.9 ppm correlated to the δH 5.1 ppm of ozonides.…”

Section: Resultssupporting

confidence: 71%

Structural characterization by Nuclear Magnetic Resonance of ozonized triolein

Díaz¹,

Gavín²,

Andrade³

2008

Grasas y Aceites

View full text Add to dashboard Cite

En el presente estudio ha sido caracterizada por RMN la trioleina ozonizada con índice de peróxidos de 739 mmolequiv/kg. La trioleina y la trioleina ozonizada muestran espectros muy similares exceptuando los valores de las resonancias δ 9,74 ppm de los protones aldehídicos, y δ 5,14 ppm (protones metínicos de los ozónidos). Otras nuevas asignaciones fueron basadas en las conectividades obtenidas por las constantes de acoplamiento escalar como δ 2,41 ppm (grupo metilénico alilico a los protones aldehídicos y protones metínicos de los ozónidos) y δ 1,67 ppm (protones metilénicos en posición β con respecto a los protones metínicos de los ozónidos). En los espectros 13 C y 1 H-13 C de la trioleina ozonizada la presencia de ozónidos fue atribuida, respectivamente, por las señales δ 104,2 y δ 104,3 ppm. Una nueva señal en δ 43,9 ppm confirma la presencia de carbono metilénico de ozónidos. Estos resultados indican que la elucidación estructural de triglicéridos ozonizados, ofrece información química relevante relacionada con los aceites vegetales ozonizados.PALABRAS CLAVE: Aldehído -Ozónidos -Ozonización -Ozono -RMN -Trioleina. SUMMARY Structural characterization by Nuclear Magnetic Resonance of ozonized triolein.In the present study ozonized triolein with 739 mmolequiv/kg peroxide index is characterized by NMR. The triolein and ozonized triolein show very similar

show abstract

Section: Resultssupporting

confidence: 71%

Structural characterization by Nuclear Magnetic Resonance of ozonized triolein

Díaz¹,

Gavín²,

Andrade³

2008

Grasas y Aceites

View full text Add to dashboard Cite

show abstract

“…18,19 However a new group of signals were found in the spectrum from ozonized methyl linoleate (Figure 4). 20 The terminal methyl carbon shift C-18 is found at δ 14 ppm.…”

Section: -17mentioning

confidence: 99%

Characterization by NMR of Ozonized methyl linoleate

Díaz

Gavín²

2007

J. Braz. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

No presente estudo o linoleato de metila ozonizado com índice de peróxidos de 1.800 mmol-equiv. kg -1 foi caracterizado quimicamente. Os efeitos do ozônio sobre o linoleato de metila produz hidroperóxidos, ozonideos e aldeídos, os quais foram identificados por técnicas de ressonância magnética nuclear de 1 H e 13 C, mono-e bidimensional. O linoleato de metila padrão e o linoleato de metila ozonizado mostram espectros muito similares, excetuando os valores de ressonância (δ 9,7 e δ 9,6) que correspondem aos hidrogênios aldeídicos (δ 5,7 e δ 5,5) e olefínicos de hidroperóxidos (δ 5,2). Outras atribuições estão baseadas nas conectividades fornecidas pelas constantes de acoplamento. Estes resultados indicam que a espectrometria de RMN pode oferecer informação valiosa a respeito da quantidade de compostos oxigenados formados à partir do linoleato de metila ozonizado para o uso em ozonoterapia e na química de óleos vegetais ozonizados.In the present study ozonized methyl linoleate with peroxide index of 1,800 mmol-equiv kg -1 was chemically characterized. Ozonation of methyl linoleate produced hydroperoxides, ozonides and aldehydes which were identified by 1 H and 13 C NMR two-dimensional. The standard methyl linoleate and ozonized methyl linoleate shown very similar 1 H NMR spectra except for the signals at δ 9.7 and δ 9.6 that correspond to aldehydic hydrogen, δ 5.7 and δ 5.5 (olefinic signals from hydroperoxides) and δ 5.2 ppm (multiplet from ozonides methynic hydrogen). Other resonance assignments are based on the connectivities provided by the hydrogen scalar coupling constants. These results indicate that NMR spectroscopy can provide valuable information about the amount of formed oxygenated compounds in the ozonized methyl linoleate in order to use it to follow up ozone therapy and chemistry of ozonized vegetable oil. 5,6 However, data on the spectra of ozonized fatty acids is scarce in the literature. KeywordsThe reaction of ozone with vegetable oil and lipids occurs almost exclusively with the carbon-carbon double bonds present in unsaturated fatty acids. Different kinds of oxygenated products are formed (hydroperoxides, ozonides and aldehydes) that probably are responsible for the biological activity of ozonized fatty acids.7-9 The mechanism of this reaction is well known (Criegee mechanism, Figure 1), as well as the conditions necessary to enhance the preferential formation of any of these oxygenated compounds. 10,11 Of all the natural fatty acids, linoleic acid is one of the most widely distributed and is present in practically all lipids. For this reason, methyl linoleate was chosen as a model compound to be ozonized and chemically Experimental General ozonization procedureA mixture of 1.6 mL (0.0048 mol L -1 ) of methyl linoleate (99%) and 0.16 mL of water were introduced into a bubbling reactor where ozone reaction took place at room temperature. 7,8 The reaction was continued during 7.25 minutes and one sample was taken at applied ozone doses 245 mg g -1 . The samples were stored at -80 °C until NMR ...

show abstract

“…Secondary ozonides of fatty acids were subjected to intensive studies (de Almeida et al, 2012;Díaz et al 2001Díaz et al , 2003Díaz et al , 2005aDíaz et al , 2005bDíaz et al , 2006Díaz et al , 2008Díaz et al , 2012Díaz Gómez et al 2004;Ledea et al 2001;Martinez Tellez et al 2006;Sadowska et al 2008;Sega et al 2010) because of their relative stability and their potential and current application as compounding ingredients in antiseptic preparations; e.g., in topical application in cosmetics (Cirlini et al 2012;de Almeida et al 2012;Ledea et al 2001). However, the interest in secondary ozonides is not limited to those derived from fatty acids but also embraces medicinal chemistry, since certain ozonides were found to display antimalarial (de Almeida- Barbosa et al 1996;Dong 2002;Kumar et al 2011;O'Neill and Posner 2004) and antihelmintic (Keiser and Utzinger 2007) activity.…”

Section: Introductionmentioning

confidence: 99%

Ethyl Oleate and Ethyl Elaidate Ozonides: Thermal Decomposition and Photolysis

Cataldo¹

2015

Ozone: Science & Engineering

View full text Add to dashboard Cite

Highly pure ethyl oleate and ethyl elaidate were ozonized to their secondary ozonides (respectively EO-SOZ and EE-SOZ). The decomposition enthalpies of EO-SOZ and EE-SOZ were determined by DSC (Differential Scanning Calorimetry) and found, respectively, at -266 kJ/mol and -264 kJ/mol, a value much closer to the theoretically calculated upper limit of -278 kJ/mol than the decomposition enthalpy of -243 kJ/mol measured on EO-SOZ prepared from an ethyl oleate sample conforming to the European Pharmacopoeia. Although a considerable amount of heat was liberated, EO-SOZ and EE-SOZ cannot be defined as explosive based on their DSC traces at a heating rate of 10 • C/min. Pure EO-SOZ and EE-SOZ show a decomposition peak at the DSCs of 137 • C and 139 • C, respectively. The thermal decomposition of EO-SOZ and EE-SOZ was studied also by FT-IR spectroscopy showing that the decomposition involves the loss of the ozonide infrared band at 1110 cm −1 and the formation of the expected decomposition products (pelargonic acid, pelargonaldehyde, ethyl azelate, etc.). The kinetics of the photochemical decomposition of EO-SOZ and EE-SOZ were studied by FT-IR spectroscopy, and the relative rate constants were determined. EO-SOZ when overozonized forms a spin adduct with nitrosobenzene and the relative nitroxyl radical was clearly detected by the Electron Spin Resonance (ESR). Secondary ozonation products known as trioxides may be responsible for these adducts.

show abstract

Spectroscopic Characterization of Ozonated Sunflower Oil

Cited by 29 publications

References 9 publications

Structural characterization by Nuclear Magnetic Resonance of ozonized triolein

Structural characterization by Nuclear Magnetic Resonance of ozonized triolein

Characterization by NMR of Ozonized methyl linoleate

Ethyl Oleate and Ethyl Elaidate Ozonides: Thermal Decomposition and Photolysis

Contact Info

Product

Resources

About