Isolation and identification of 2‐pentenylfurans in the reversion flavor of soybean oil

Chang, Stephen S.; Shen, Guo-Hui; Tang, Jian; Jin, Qi; Shi, Huang; Carlin, James T.; Ho, Chi‐Tang

doi:10.1007/bf02679785

Cited by 25 publications

(11 citation statements)

References 12 publications

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“…There is however another possible pathway for the production of furans, which has never been suggested in dairy products, i.e. the oxidation of polyunsaturated fatty acids [17]. In our study, the total amount of furans in cheese was correlated with the proportion of polyunsaturated fatty acids in the milk (R 2 = 0.62, P < 0.001).…”

Section: Volatile Compounds In Cheesesupporting

confidence: 38%

Relationships between flavour and chemical composition of Abondance cheese derived from different types of pastures

Bugaud

Buchin

Hauwuy

et al. 2001

Lait

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-The relationships between the flavour and composition of half-cooked pressed Abondance cheese (Haute-Savoie, France) were studied under natural cheese production conditions on the basis of different pastures exploited by 3 producers. Cheeses manufactured from milk produced from mountain pastures (M, n = 5, 1500-1850 m) were deemed to be more "fruity", "animal", "boiled milk" and "hazelnut" and less pungent and "propionic acid" than cheeses made from milk produced from valley pastures (V, n = 5, 850-1100 m). It was possible to partly attribute these differences in flavour to the presence of protein-based volatile compounds in the cheeses. The V cheeses had a greater variety of flavours than the M cheeses. Cheeses from gramineae-rich pastures had the most intense "cooked cabbage" odours, related to the greater amounts of sulphur compounds in these cheeses. Terpenes, which are more abundant in cheeses produced from dicotyledon-rich pastures, did not contribute directly to cheese aroma. The differences in flavour between the cheeses manufactured by the 3 producers were of the same magnitude as those observed between different pastures used by a same producer. The origin of the volatile compounds in the cheeses -whether of microbial origin or from the feed -was discussed.cheese / flavour / volatile compound / proteolysis / pasture Résumé -Relations entre la flaveur et la composition chimique de fromages d'Abondance fabriqués à partir de laits produits sur différents types de pâturages. Les relations entre la flaveur et la composition des fromages à pâte pressée demi-cuite de type Abondance (Haute-Savoie, France), ont été étudiées dans des conditions naturelles de production du fromage à partir de pâturages diffé-rents exploités par 3 producteurs. Les fromages fabriqués à partir de laits produits sur des pâturages de montagne (M, n = 5, 1500-1850 m) ont été jugés plus « fruité », « animal », « lait cuit » et « noisette » et moins piquant et « propionique » que les fromages issus de laits produits sur des pâturages de vallée (V, n = 5, 850-1100 m). Ces différences de flaveur ont pu être attribuées en partie à la présence dans les fromages de composés volatils issus du catabolisme des acides aminés. Les fromages V présentaient une plus grande diversité de flaveur que les fromages M. Les fromages issus de pâturages riches en graminées étaient les plus intenses en odeur « chou cuit », flaveur liée aux quantités plus importantes de composés soufrés dans ces fromages. Les terpènes, plus abondants dans les fromages issus de pâturages riches en dicotylédones, n'ont pas contribué directement à l'arôme des fromages. Les différences de flaveur des fromages entre les 3 producteurs ont été du même ordre de grandeur que celles observées chez un même producteur entre différents pâturages. Les origines microbienne et alimentaire des composés volatils des fromages ont été discutées.fromage / flaveur / composé volatil / protéolyse / pâturage

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Section: Volatile Compounds In Cheesesupporting

confidence: 38%

Relationships between flavour and chemical composition of Abondance cheese derived from different types of pastures

Bugaud

Buchin

Hauwuy

et al. 2001

Lait

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show abstract

“…A beany flavor, which is a unique and undesirable flavor in soybean oil with low peroxide value, has been a problem for the last 70 years and studied extensively both nationally and internationally (Chang and others 1966; Smouse and Chang 1967). 2‐Pentylfuran and pentenylfuran were reported to be responsible for the beany flavor (Chang and others 1966, 1983; Smouse and Chang 1967; Ho and others 1978; Smagula and others 1979), and 1 O 2 was involved in their formation from linoleic and linolenic acids present in soybean oil, as shown in Figure 9 and 10 (Min and others 2003). Min and others (2003) strongly indicated that the reversion flavor of soybean oil can be decreased or eliminated by removing chlorophylls from the oil during processing.…”

Section: Singlet Oxygen Formation and Mechanisms Of Photosensitized Omentioning

confidence: 99%

Mechanisms and Factors for Edible Oil Oxidation

Choe¹,

Min²

2006

Comp Rev Food Sci Food Safe

1,482

1,210

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Edible oil is oxidized during processing and storage via autoxidation and photosensitized oxidation, in which triplet oxygen ( 3 O 2 ) and singlet oxygen ( 1 O 2 ) react with the oil, respectively. Autoxidation of oils requires radical forms of acylglycerols, whereas photosensitized oxidation does not require lipid radicals since 1 O 2 reacts directly with double bonds. Lipid hydroperoxides formed by 3 O 2 are conjugated dienes, whereas 1 O 2 produces both conjugated and nonconjugated dienes. The hydroperoxides are decomposed to produce off-flavor compounds and the oil quality decreases. Autoxidation of oil is accelerated by the presence of free fatty acids, mono-and diacylglycerols, metals such as iron, and thermally oxidized compounds. Chlorophylls and phenolic compounds decrease the autoxidation of oil in the dark, and carotenoids, tocopherols, and phospholipids demonstrate both antioxidant and prooxidant activity depending on the oil system. In photosensitized oxidation chlorophyll acts as a photosensitizer for the formation of 1 O 2 ; however, carotenoids and tocopherols decrease the oxidation through 1 O 2 quenching. Temperature, light, oxygen concentration, oil processing, and fatty acid composition also affect the oxidative stability of edible oil.

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“…At concentration levels of 1-10 mg/kg these compounds impart characteristic beany, grassy, metallic, liquorice and buttery flavours to various oils (Table 6.3). Chang et al (1966) suggested the fonnation of 2-pentylfuran from 4-ketononanal, possibly derived from oxidised linoleic acid:…”

Section: Furansmentioning

confidence: 99%

Oxidative pathways to the formation of off-flavours

Kochhar¹

1996

Food Taints and Off-Flavours

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Isolation and identification of 2‐pentenylfurans in the reversion flavor of soybean oil

Cited by 25 publications

References 12 publications

Relationships between flavour and chemical composition of Abondance cheese derived from different types of pastures

Relationships between flavour and chemical composition of Abondance cheese derived from different types of pastures

Mechanisms and Factors for Edible Oil Oxidation

Oxidative pathways to the formation of off-flavours

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