Retro‐aldol degradations of unsaturated aldehydes: Role in the formation ofc4‐heptenal fromt2,c6‐nonadienal in fish, oyster and other flavors

Josephson, David B.; Lindsay, R.C.

doi:10.1007/bf02546268

Cited by 92 publications

(68 citation statements)

References 26 publications

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“…It was detected in fish oil [18,26] and fish oil-enriched mayonnaise [22] but was found to be absent after the frozen storage of salmon [19]. The absence of 4-(Z)-heptenal during the oxidation process suggested that retro-aldol degradation from the conversion of 2, 4-(E,Z)-nonadienal to yield this volatile, as proposed elsewhere [34], did not occur. On the basis of PV, AV and 1-penten-3-one determinations (Fig.…”

Section: Oxidative Stability Of the Oilmentioning

confidence: 69%

Volatile oxidation products formed in crude herring oil under accelerated oxidative conditions

Aidos

Jacobsen

Jensen

et al. 2002

Eur. J. Lipid Sci. Technol.

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Volatile oxidation products formed in crude herring oil under accelerated oxidative conditionsCrude fish oil produced from herring byproducts was evaluated on its oxidative stability by a number of complementary methods. The oil was placed in a closed vessel, exposed to pure oxygen, and kept at 50 °C for up to 53 h. Six volatile compounds contributing to off-flavor in the oil were followed over time. Simultaneously, conventional oxidative chemical measurements were carried out. The results showed that, apart from 4-(Z)-heptenal, all the other components increased with time. The rate of formation of fluorescent compounds, being only time-dependent, showed to be the simplest model to describe the progress of oxidation, in opposition to the development of hexanal. Development of 1-penten-3-one correlated well with peroxide and anisidine values (r = 0.938 and r = 0.931, respectively). Correlations between the volatiles were also found. Within the applied conditions, 1-penten-3-one and 2,4-(E,E)-heptadienal could be useful as volatiles indicators for the oxidative status of the oil.

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Section: Oxidative Stability Of the Oilmentioning

confidence: 69%

Volatile oxidation products formed in crude herring oil under accelerated oxidative conditions

Aidos

Jacobsen

Jensen

et al. 2002

Eur. J. Lipid Sci. Technol.

View full text Add to dashboard Cite

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“…However, these workers were unable to account for the presence of cis-4-heptenal by accepted autoxidation mechanisms. Josephson and Lindsay (1987) discovered that the retro-aldol condensation of trans-2,cis-6-nonadienal resulted in the formation of cis-4-heptenal, and thus accounted for its close association with lipid oxidation and cooking where its formation is greatly accelerated. Although cis-4-heptenal does not appear to possess a fishy flavour, it causes a pronounced potentiation of the fishiness contributed by the 2,4,7-decatrienals (Karahadian and Lindsay, 1989).…”

Section: Deterioration Of Fish Flavoursmentioning

confidence: 98%

Flavour of fish

Lindsay¹

1994

Seafoods: Chemistry, Processing Technology and Quality

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Very fresh fish are characterized by mild, delicate flavours and aromas that are contributed by volatile 6-, 8-, and 9-carbon carbonyls and alcohols arising from the action of lipoxygenases on long-chain polyunsaturated fatty acids. In marine fish these green, planty, and melony flavour notes are usually accompanied by various sea-like or iodine-like flavour notes that are provided by bromophenols that are accumulated from the environment via the food chain. The flavour of prime salmon results in part from the co-oxidation of carotenoid pigments and polyunsaturated fatty acids which yield characterizing aroma compounds. Flavour quality deterioration in fish is caused by microbial activity and endogenous enzymic activity which results in the destruction of some compounds and the formation of others. When autoxidation of unsaturated fish lipids progresses to a stage where 2,4,7-decatrienals and other carbonyls occur above threshold values, fishiness or cod liver oil-like flavours become apparent. Chemical alterations of volatile compounds during storage and processing also contribute to various fish flavours. Very fresh fish flavoursVery fresh flavours and aromas are characterized by mild, green, and planty notes that are easily recognized and readily associated with fresh fish. Depending on the nature of the fish, very fresh flavours are often accompanied by species-related flavours, such as those encountered for salmon. The chemical basis of the fresh fish flavour system is centred in the polyunsaturated fatty acids of fish lipids. The major flavour impact compounds are several 6-, 8-, and 9-carbon aldehydes, ketones, and alcohols which are derived from the fatty acids via specific lipoxygenase activity (Josephson and Lindsay, 1986). While some researchers have argued that NADH-dependent microsomal oxidase (Shewfelt et ai., 1981;Slabyj and Hultin, 1984) and a myeloperoxidase (Kanner and Kinsella, 1983; Kanner et aI., 1986)

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“…It is the retro-aldol condensation product of 2,6-nonadienal, which is also listed in Table 3. This latter compound, strongly reminiscent of cut cucumber, is in turn an oxidation product of linolenic acid (Josephson & Lindsay 1987a, 1987b. These researchers found that 4-heptenal was the dominant off-odour in reheated boiled potatoes.…”

Section: Possible Causes Of Pastoral Flavourmentioning

confidence: 99%

The effect of diet on the flavour of cooked beef and the odour compounds in beef fat

Young¹,

Baumeister²

1999

New Zealand Journal of Agricultural Research

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Fatty meat from cattle finished for nine weeks on ryegrass/clover or maize was evaluated for intensity of pastoral odour and flavour by a sensory panel. Although there was no significant treatment effect for intensity, panellists' comments indicated that even this short period on a maize diet could change descriptions of odour and flavour; when assessed by independent assessors, the pasture treatment had a much lower ratio of "favourable" to "unfavourable" comments (P < 0.01). Odorous compounds in fat from the two treatments were examined by odourport sniffing, where compounds eluting from a gas chromatographic column were described, and identified where possible. Two "sniffers" semiquantitatively evaluated the fat volatiles, first trapped on Tenax then resolved on a column. Comparisons between treatments were largely unproductive. However, particularly odorous compounds were tentatively identified along with others of interest with respect to dietary origins. Compounds included 4-heptenal (and/or the coeluant heptanal), l-octen-3-ol, nonanal, 2,6-nonadienal, nonanoic acid, and the faecal-smelling compound indole. 4-Methylphenol was not detected by sniffing but was present in the fat headspace. The chemical origins of these compounds are discussed in relation to diet. A98056

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Retro‐aldol degradations of unsaturated aldehydes: Role in the formation ofc4‐heptenal fromt2,c6‐nonadienal in fish, oyster and other flavors

Cited by 92 publications

References 26 publications

Volatile oxidation products formed in crude herring oil under accelerated oxidative conditions

Volatile oxidation products formed in crude herring oil under accelerated oxidative conditions

Flavour of fish

The effect of diet on the flavour of cooked beef and the odour compounds in beef fat

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