Partial Characterization of the Flavors of Oxidized Butteroil

El-Negoumy, A.M.; Miles, D.M.; Hammond, Earl G.

doi:10.3168/jds.s0022-0302(61)89855-x

Cited by 18 publications

(5 citation statements)

References 16 publications

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“…1148 redeodorization in the laboratory. The flavor compounds were isolated from oil in flavor stage "A" by slowly passing it through a Rota-Fibu still at or above room temperature (5). The flavor components were collected in a liquid nitrogen-cooled trap.…”

Section: Methodsmentioning

confidence: 99%

“…Thinlayer chromatography was carried out on Silica gel G (7) and Silica gel G-silver nitrate (1) using petroleum ether with 4 to 7% diethyl ether as the mobile phase. The paper chromatography was carried out on kerosene impregnated paper, with methanolethanol water, 10:10:5, as the mobile phase (5). Partition column chromatography was carried out on nitromethane-Skellysolve B columns (3).…”

Section: Methodsmentioning

confidence: 99%

“…Commercially available catalysts have selectivity ratios (Klinolenate/Klinoleate) of 1.8-2.9 (3,4). A ratio of 4 or greater, as calculated on an analog computer (5), is required to reduce the linolenate content in a liquid soybean oil to 2% or less without substantial loss of linoleate or increase in high melting glyeerides, and such ratios increase the yield of liquid oil during winterization or may eliminate the need for that processing step.…”

Section: Introductionmentioning

confidence: 99%

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Studies on the flavor of autoxidized soybean oil

Hill

Hammond

1965

J Americ Oil Chem Soc

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The flavor components of soybean oil in the early stages of autoxidation were isolated by distillation in a molecular still. The distillate consisted of an aqueous layer and an oily fihn. The oily film did not reproduce the autoxidized flavor when added to freshly deodorized oil. Gas chromatographic and organoleptic analysis indicated that the oily film contained hexanal, vinylamyl ketone, and tra~s,cis-2,6-nonadienal. The aqueous layer reproduced the autoxidized flavor when added to freshly deodorized oil, and the flavor had a retention time on butandiol suecinate columns between those of pentanal and hexanah Mixtures of vinylethyl ketone and pentanal gave a flavor to freshly deodorized oil similar to the flavor of oil in the early stages of autoxidation. Vinytethyl ketone was identified in the distillate from autoxidized soybean oil as the 2,4-dinitrophenylhydrazone.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Studies on the flavor of autoxidized soybean oil

Hill

Hammond

1965

J Americ Oil Chem Soc

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“…In the period 1944-47, however, Van der Waarden (5,6) established that this opinion was false; he made a suggestion, based partly on experimental evidence, that possibly unsaturated aldehydes with the double bond not in conjugation with the carbonyl group might be responsible for the off-flavor. Later Pont et al (7), Forss et al (8), Stark and Forss (9) and E1-Negoumy et al (10) carried out investigations in the same direction. Badings (11) A whale oil flavor can also be observed in strongly autoxidized soybean (13) and linseed oils (14), and, more easily, in autoxidized fish oils.…”

Section: Introductionmentioning

confidence: 92%

2‐trans,4‐cis,7‐cis‐Decatrienal, the fishy off‐flavor occurring in strongly autoxidized oils containing linolenic acid or ω 3,6,9, etc., fatty acids

Meijboom

Stroink

1972

J Americ Oil Chem Soc

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A possible decomposition product of oils containing unsaturated fatty acids with the double bond pattern 603,6,9 or 603,6,9, etc., is 2-trans,4-cis, 7-cis-decatrienal. It has therefore been investigated whether this trienal is present in strongly autoxidized linolenic acid, soybean, linseed and fish oils. Via a degassing technique the carbonyls from the samples of oils heated in a closed system under nitrogen were collected and separated as their 2,4-dinitrophenylhydrazones (DNPHs) by thin layer chromatography (TLC). The presence of 2-trans,4-cis,7-cis-decatrienal in the samples was positively established by TLC, UV absorption and mass spectroscopy of its DNPH. All analytical data established the complete identity of the isolated DNPH with a synthesized 2,4,7-decatrienal-DNPH. The free aldehyde obtained on hydrolysis of the alkatrienal-DNPH in question had the same flavor as authentic 2-trans,4-cis,7-cis-decatrienal, having a fish or rather a whale oil flavor.

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“…Hammond and his colleagues at Iowa State University studied the volatile compounds from oxidized butterfat and from oxidized linseed, safflower and herring oils (El-Negoumy & Hammond, 1960;El-Negoumy, Miles & Hammond, 1961) as well as their relation to oxidized linoleate and linolenate esters (Hammond, El-Negoumy & de Puchal, 1961). These workers reported that an unidentified carbonyl compound occurring in minute amounts and with similar gas-chromatographic properties to our ' metallic compound' was chiefly responsible for the oxidized flavour of these oils and linoleic acid.…”

mentioning

confidence: 99%