Hydroperoxide formation during autoxidation of conjugated linoleic acid methyl ester

Hämäläinen, Taina I.; Sundberg, Susanna; Mäkinen, Marjukka; Kaltia, Seppo; Hase, Tapio; Hopia, Anu

doi:10.1002/1438-9312(200109)103:9<588::aid-ejlt5880>3.3.co;2-c

Cited by 11 publications

(18 citation statements)

References 10 publications

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“…Some authors have already reported its presence in oxidized CLA samples, assuming that this volatile compound could be formed by decomposition of 12‐hydroperoxide‐ trans ‐8, trans ‐10‐octadecadienoate. The latter represents one of the probable hydroperoxides formed during the oxidation of methylated cis ‐9, trans ‐11‐CLA . Differently from García‐Martínez et al , in this research heptanal has been found also in LA model systems, in much lower contents (about 2%) with respect to CLA forms.…”

Section: Resultscontrasting

confidence: 65%

Volatile compounds as indicators of conjugated and unconjugated linoleic acid thermal oxidation

Cossignani

Giua

Simonetti

et al. 2014

Euro J Lipid Sci & Tech

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In this research, volatiles arising from heating of conjugated (CLA) and unconjugated (LA) linoleic acid, in different chemical forms (free acids, methyl esters, and homogeneous TAGs) have been studied. A solid phase micro-extraction (SPME) coupled with GC-MS was used to analyze the volatile compounds produced during heating at 180°C for different times (15, 30, 45, and 60 min). Numerous types of volatiles have been identified such as aldehydes, furan fatty acids (FA), alcohols, methyl esters, and methyl-oxoacids. Results showed that aldehydes were the main volatile compounds both in CLA and LA, even if some differences were found between conjugated and unconjugated systems. In particular, heptanal and trans-2octenal were detected mainly in CLA forms, while trans-2-heptenal in LA. Among furan FA, 2-pentyl-furan content was higher in LA than in CLA at all treatment times, while 2-hexyl-furan was detected in free fatty acid and methyl ester forms of CLA and it was never detected in LA model systems. Among alcohols, 1-octen-3-ol was found only in LA forms. Methylated forms of CLA and LA provided high contents of methyl esters, among which methyl octanoate was the most represented. Therefore heptanal, trans-2-octenal, 2-hexylfuran could be considered as characteristic compounds produced during CLA-rich sample oxidation.Practical applications: Nowadays CLA, known for its interesting beneficial health effects both on animals and humans, is widely used as functional component in numerous foods and nutritional supplements. Besides the more common TAG form, CLA is used also as free fatty acids and methyl esters. To date, studies on CLA oxidation are scarce and the results are sometimes contradictory. For this reason, the comparison of the volatile compounds obtained from different model systems of CLA and LA could be useful to deepen knowledge on secondary oxidation products of some chemical forms of interest for pharmaceutical formulae and CLA-rich oils. In fact, it is very important to know the secondary products typical of CLA-and LA-based matrices to identify characteristic oxidation compounds of CLA and LA products.Abbreviations: FA, fatty acid; FFA, free FA; LA, linoleic acid; Me-CLA, CLA methyl ester; Me-LA, LA methyl ester; SPME, solid phase micro-extraction; Tri-CLA, homogeneous TAG of CLA; Tri-LA, homogeneous TAG of LA Eur.

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Section: Resultscontrasting

confidence: 65%

Volatile compounds as indicators of conjugated and unconjugated linoleic acid thermal oxidation

Cossignani

Giua

Simonetti

et al. 2014

Euro J Lipid Sci & Tech

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“…As hydroperoxides are formed in the early stages of UFA oxidation, often too are conjugated double bonds (DBs) . In the case of oxidized UFAs with two conjugated DBs, these are referred to as conjugated dienes (CDs), whereas three conjugated DBs are considered conjugated trienes (CTs).…”

Section: Historically Common Methods To Assess Ufa Oxidation In Storagementioning

confidence: 99%

Update on the methods for monitoring UFA oxidation in food products

Kerrihard

Pegg

Sarkar

et al. 2014

Euro J Lipid Sci & Tech

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Unsaturated fatty acids (UFAs) as well as natural food ingredients containing them are being added to food products more often. Unfortunately, UFAs are susceptible to oxidative degradation, and can therefore reduce the stability of a food matrix. The assessment of oxidation and stability of lipids has never been standardized, and has long included a variety of approaches. These techniques can differ greatly in the reactions/compounds being assessed, and therefore the eventual conclusions may be affected dramatically by selection of methodology. The aim of this review is to provide an update on the methods of historic and current use for the assessment of lipid stability in food products. Accelerated storage tests, assessment methods of lipid oxidation, and rapid indicators of stability are discussed in the contexts of their modern prominences, uses, and concerns.

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“…However, from an in vitro study, Van Den Berg et al (6) suggested that CLA is a pro-oxidant. Subsequently, the oxidative stability of CLA was examined under various conditions (7)(8)(9)(10)(11). CLA in the FFA form was found to be extremely unstable; its stability is similar to that of DHA and its oxidation rate is considerably greater than that of LA, linolenic acid (LnA), and arachidonic acid (8,10).…”

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Oxidation rate of conjugated linoleic acid and conjugated linolenic acid is slowed by triacylglycerol esterification and α‐tocopherol

Tsuzuki

Igarashi

Iwata

et al. 2004

Lipids

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We have recently shown that alpha-eleostearic acid (alpha-ESA), a conjugated linolenic acid, has a stronger antitumor effect than conjugated linoleic acid (CLA), both in vitro and in vivo. In this study, the oxidative stability of alpha-ESA was examined compared with linoleic acid (LA), alpha-linolenic acid (LnA), and CLA. Thin layers of the FA (LA, 9Z,11 E-CLA, 10E,12Z-CLA, LnA, and alpha-ESA) were auto-oxidized at 37 degrees C, and the FA remaining, the absorbed oxygen volume, the lipid hydroperoxide content, and the TBARS content were determined. The oxidation rate of alpha-ESA was faster than that of the unconjugated FA and CLA (9Z, 11 E-CLA and 10E, 12Z-CLA). However, the lipid hydroperoxide and TBARS contents following alpha-ESA oxidation were low, suggesting production of only small amounts of rapid-reacting secondary oxidation products. Furthermore, the oxidative stability of conjugated FA (CLA and CLnA) in which the carboxylic acid group was esterified with triacylglycerol was greater than that of the FFA. Addition of an antioxidant (alpha-tocopherol) also increased the stability of the conjugated FA to a level similar to that of the unconjugated FA.

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Hydroperoxide formation during autoxidation of conjugated linoleic acid methyl ester

Cited by 11 publications

References 10 publications

Volatile compounds as indicators of conjugated and unconjugated linoleic acid thermal oxidation

Volatile compounds as indicators of conjugated and unconjugated linoleic acid thermal oxidation

Update on the methods for monitoring UFA oxidation in food products

Oxidation rate of conjugated linoleic acid and conjugated linolenic acid is slowed by triacylglycerol esterification and α‐tocopherol

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