Possible mechanisms of autoxidative rancidity

Loury, M.

doi:10.1007/bf02533075

Cited by 78 publications

(50 citation statements)

References 9 publications

(6 reference statements)

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“…Entre los ácidos grasos insaturados precursores de hexanal destaca el ácido linoleico (Ellis et al, 1968) (Henderson et al, 1980) (Frankel et al, 1981), principalmente a través de la oxidación a 13-monohidroperóxidos, aunque también se pueda formar de los 9-monohidroperóxidos, pero en cantidades más reducidas (Chan et al, 1976). La oxidación del ácido oleico puede originar porcentajes muy pequeños de alcanales volátiles C2-C6, porque este ácido insaturado suele degradarse con preferencia en aldehidos insaturados, a través de una beta-escisión de sus hidroperóxidos (Loury, 1972). También una pequeña cantidad de propanal se puede formar en la oxidación del ácido linolénico y sus homólogos w3 (Grosch, 1987).…”

Section: Tabla 11unclassified

La oxidación de componentes grasos y formación de hexanal en la curación del salchichón

Chasco¹,

Beriain²,

Bello³

1992

Grasas y Aceites

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RESUMENLa oxidación de componentes grasos y formación de hexanai en la curación del salchichón Se ha estudiado la formación de aicanales de cadena corta (C3-C6) durante el proceso de curación de un salchichón estándar elaborado en planta piloto. Se ha comparado sus contenidos finales con los obtenidos para otros tres lotes de salchichón de fabricación industrial (I, II. III). Con excepción del hexanai, que se encuentra en cantidades importantes, los otros tres aldehidos aparecen en cantidades muy reducidas o incluso no se detectan. No se ha obtenido una correlación estadística entre el contenido en hexanai y los niveles de oxidación de los componentes grasos valorados a través del índice de peróxidos, el número T.B.A. o los compuestos carbonilos totales.Sin embargo, sí existe una cierta correlación entre el contenido en hexanai y las relaciones oleico/linoleico de cada lote de salchichón. La ausencia de hexanai en todos los salchichones del lote II viene correspondida por una mayor proporción de ácido linoleico entre sus AGL. Se propone la determinación de hexanai como un modo útil de comprobar si el mecanismo oxidative de las grasas durante el proceso de curación ha sido correcto. PALABRAS-CLAVE: HexanaiLipidie components oxidation and hexanai formation during the curing of saucisson It has studied formation of alcanals of low weight (03-06) during the curing of standard Saucisson manufactured in pilot plant. Aldehydes content have been compared to others obtained in three batches of industrial process (I, li y III). Except to hexanai, present in important amounts, the rest of aldehydes appear in reduced levels even are not detected. Statistical correlation has not been obtained between hexanai content and oxidation levels of lipidie components titrated by peroxides value, T.B.A. number or total carbonyl compounds. However, certain correlation has been found between hexanai content and ratio of oleic/linoleic of each batch of saucisson. Absence of hexanai in all of saucissons of batch II is corresponded by a greater proportion of linoleic acid between their A.G.L. It is proposed determination of hexanai like an useful method to check whether oxidative mechanism of lipids during the curing has been corrected. KEY-WORDS: Curing process Saucisson.Hexanai -Lipidie oxidationdación en su proceso de maduración-desecación, dando lugar a un núnnero importante de sustancias volátiles entre ellas aldehidos (Bailey et al., 1980). Este conjunto de reacciones en el que toman parte los lípidos desempeña un papel importante en el desarrollo del aroma típico de cada embutido (Shahidi, 1989), a través de mecanismos todavía no bien comprendidos (Gray et al., 1984). Una de las reacciones que se considera más relevante en este proceso es la oxidación del ácido linoleico, que lleva a la formación de hexanai (Ellis et al., 1968) (Henderson et al., 1980) (Frankel et al., 1981. La valoración del contenido en este aldehido se ha propuesto como una fórmula válida para predecir la calidad de algunos aceites vegetales (Dupuy et al., 1976) ...

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Section: Tabla 11unclassified

La oxidación de componentes grasos y formación de hexanal en la curación del salchichón

Chasco¹,

Beriain²,

Bello³

1992

Grasas y Aceites

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“…Presumably ethylene might have been formed in higher yield, except for the fact that using the aldehyde self-quenching becomes serious (10). No poxygenase (16), the a peroxidation of aldehydes, leading to formic acid and the next lower homologue, may be expected to occur in vivo and has, indeed, been postulated (17). Therefore, our results indicate the possibility that another route to ethylene may exist in plants, in addition to the well-known formation from 1-aminocyclopropane-1-carboxylic acid (18).…”

Section: Methodsmentioning

confidence: 99%

Plant hormone ethylene is a Norrish type II product from enzymically generated triplet 1-butanal.

Knudsen

Čampa

Stefani

et al. 1994

Proc. Natl. Acad. Sci. U.S.A.

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The peroxidase-catalyzed aerobic oxidation of a linear aldehyde, leading to the next lower homologue in the triplet state, is accompanied by Norrish type H product ethylene when the substrate is pentanal. This system appears to provide an example of "photobiochemistry without light" because ethylene is a plant hormone and is formed in lipid peroxidation when the recurrent oxidation of linear aldehydes occurs. In this work, we report a study ofthis reaction as a function of aldehyde chain length and show that, when pentanal is the substrate, the reaction is accompanied by the formation of the predicted Norrish type II (5) product ethylene. MATERIALS AND METHODSThe aldehydes (Fluka), HRP (types VI, I, and II; Sigma), and eosine (Merck) were commercially available. Aldehydes were stored under N2 at -20°C. The trimethylsilylenol ethers of pentanal and of butanal were prepared according to Cazeau et al. (6).Unless otherwise stated, HRP type VI was used throughout the work; it was sufficiently pure, as attested to by the reproducibility of results in this and in all previous work, even when subjected to further purification. The absence of detectable amounts of ethylene in the absence of aldehydes (see Results and Discussion) indicates that the HRP used contains no ethylene-producing endogenous substrate.Comparative oxygen consumption by the C2-C6 aldehydes in the presence of HRP necessary for the experiments with eosine was ascertained in a Warburg apparatus. The (slow) rate of oxygen uptake was as follows: C2 < C3 < C4 = C5 = The publication costs of this article were defrayed in part by page charge payment. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. §1734 solely to indicate this fact.C6. When the trimethylsilylenol ethers were used as substrates, oxygen uptake was measured in a Yellow Springs Instruments model 53 oxygen monitor.The experiments with eosine were done at 40°C in 0.5 M phosphate/0.04 M sodium pyrophosphate buffer, pH 7.4/0.5 M ethanol/10 ,uM eosine/1 x 10-4 M hydrogen peroxide/2 mM, 4 mM, or 8 mM aldehyde; total volume was 3 ml. The reaction was initiated by HRP addition (final concentration, 2 ,uM); under these conditions eosine is stable. Light emission was measured in a Hamamatsu model TUC-767 photon counter provided with a Hamamatsu R-562 photomultiplier tube.The experiments with the trimethylsilylenol ethers of pentanal and of butanal were done at 37°C in 0.01 M Tris buffer, pH 7.4/2 mM substrate/4 ,uM HRP. The reaction was initiated by adding 1 x 10-4 M hydrogen peroxide. The system was incubated for 10 min in a 124-ml round-bottom flask sealed with a Teflon-lined rubber septum.The experiments with butanal and propanal were done at 37°C in 0.5 M phosphate buffer, pH 7.4/0.04 M sodium pyrophosphate/1 x 10-4 M hydrogen peroxide/8 mM aldehyde (freshly distilled). The reaction was initiated by adding 1 X 10-4 M hydrogen peroxide. The incubation (as above) was for 50 min. Regarding hydrogen peroxide use in all these systems, note that hydrogen per...

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“…Aldehydes detected in the oxidation process include hexenals [10], heptenals, propanal [11,12 ] and 2,4-heptadienal [12]. Short chain aliphatic acids and alcohols have also been detected [13,14]. Increase acidity due to formation of organic acids increases corrosion.…”

Section: Oxidation Stabilitymentioning

confidence: 99%

Effects of Raw Materials and Production Practices on Biodiesel Quality and Performance

Rodríguez¹

2011

Biodiesel- Quality, Emissions and by-Products

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Possible mechanisms of autoxidative rancidity

Cited by 78 publications

References 9 publications

La oxidación de componentes grasos y formación de hexanal en la curación del salchichón

La oxidación de componentes grasos y formación de hexanal en la curación del salchichón

Plant hormone ethylene is a Norrish type II product from enzymically generated triplet 1-butanal.

Effects of Raw Materials and Production Practices on Biodiesel Quality and Performance

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