Studies to Determine the Nature of the Damage to the Nutritive Value of Some Vegetable Oils from Heat Treatment III. The Segregation of Toxic and Non-Toxic Material from the Esters of Heat-Polymerized Linseed Oil by Distillation and by Urea Adduct Formation

Crampton, E. W.; Common, R. H.; Farmer, Florence A.; Wells, Arthur F.; Crawford, Donna

doi:10.1093/jn/49.2.333

Cited by 111 publications

(18 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The feed consumption and wt gain data presented in Table I, especially with respect to animals fed 8 and 10% protein, showed trends which were observed by others who reported wt gains among animals fed various heated unfractionated fats (1)(2)(3)11,12). Altered organ wts, modified enzyme activities, and an acceleration in the formation of certain types of abnormal tissue have been reported in animals fed heated fats (22).…”

Section: Discussionsupporting

confidence: 67%

“…Many studies have been conducted in which a heat-abused fat or fractions from such fats were fed (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12). Such heated oils produced adverse nutritional and physiological conditions when fed to laboratory animals as parts of normal diets (8)(9)(10)(11)(12). Moreover, the non-urea adduct forming fatty acids, a concentrate of the cyclic fatty acids and other polar materials present in such oils, caused a high number of deaths among rats fed this material (11).…”

Section: Introductionmentioning

confidence: 99%

“…Although studies of others (8)(9)(10)(11)(12) have shown that cyclic fatty acids in diets cause adverse physiological effects when fed to rats, these diets contained only uncharacterized concentrated fractions fed at relatively high levels rather than the pure cyclic fatty acids themselves. In the present work, the nutritional effects of low levels of highly purified isomeric w(2-alkyl cyclohexadienyl) carboxylic acids in nutritionally adequate diets containing different levels of protein (casein) were determined.…”

Section: Introductionmentioning

confidence: 99%

“…Such heated oils produced adverse nutritional and physiological conditions when fed to laboratory animals as parts of normal diets (8)(9)(10)(11)(12). Moreover, the non-urea adduct forming fatty acids, a concentrate of the cyclic fatty acids and other polar materials present in such oils, caused a high number of deaths among rats fed this material (11). Repeated studies of the non-urea adduct forming fraction from heated oils have identified disubstituted aromatic and alicyclic fatty acids as major and minor components of these fats (13)(14)(15)(16).…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Nutritional effects of the cyclic monomers of methyl linolenate in the rat

Iwaoka

Perkins

1976

Lipids

View full text Add to dashboard Cite

Low levels (0.0075, 0.0225, and 0.15%) of cyclic fatty acid methyl esters (greater than 98% pure) were incorporated into diets of weanling rats fed different levels of protein. Animals on low protein diets (8-10% casein) exhibited decreased wt gains and feed consumption with increasing levels of cyclic esters in their diets after 6 weeks. Liver enlargements due to a significant (P less than 0.01) accumulation of liver lipid were noted in animals receiving 0.15% cyclic fatty acid esters in their diets.

show abstract

Section: Discussionsupporting

confidence: 67%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Nutritional effects of the cyclic monomers of methyl linolenate in the rat

Iwaoka

Perkins

1976

Lipids

View full text Add to dashboard Cite

show abstract

“…It is thus evident that nonadduct-forming monomers from methyl linoleate possess a lethal effect although to a lesser degree than similar fractions from heated linolenic acid-rich oils (6). This weaker toxic activity, as well as the very small amounts of this fraction formed Oll heating linoleic acid-rich oils, may explain the lack of harmful effects found when sunflower seed and soybean oils were tested by Cranlpton.…”

Section: Resultsmentioning

confidence: 99%

Nutritive value of methyl linoleate and its thermal decomposition products

Bottino

1962

J Americ Oil Chem Soc

View full text Add to dashboard Cite

Methyl linoleate was heated for 10 hrs. at 300~ in the absence of air and fractionated by alembic distillation and urea adduct-formation.Intestinal absorptions of the urea adduct-fornling monomeric nonadduct-forming nlonomeric, and dimeric fractions were determined. It was found that dimers were half as well absorbed as the monomers.When fed to rats, dimers were better accepted and exhibited some toxicity symptoms different from the nonadduct-fornling monomers. The dinlers caused diarrhea, irritability, and loss of hair during the early period of administration. The nonadduct-forming monomers were lethal and produced an increase in liver weight. Both fractions depressed growth. HEATING Of unsaturated oils in the absence of air is known to result in the formation of a mixture of monomeric and polymeric substances, both linear and cyclic. For reviews on the nutritional significance of such compounds the reader is referred to the papers of Brown (1) and of Rice et al. (2).Crampton and co-workers (3,9) have been able to demonstrate that, when linseed, soybean, and sunflower oils are heated at approximately 275~ for 12 to 26 hrs. in a C02 atmosphere, a polymeric fraction, which is very slightly absorbed from the intestine of the rat, and a nonurea adduct-forming monomerie fraction, which is harmful to the same animal, are formed. Comparison of the fatty acid composition of these oils with their deleterious action indicates that linolenic acid is the main precursor. Nevertheless some toxicity has been found to develop in heated oils containing relatively high proportions of linoleic add and no linolenie acid.More unsaturated oils, such as fish oils, seem able to develop toxic effects and form poorly absorbed substances if heated and administered under similar conditions (10-15).Methyl and ethyl linoleate seem also capable of forming cyclic and polymeric substances by heating, as has been suggested by Paschke et al. (16,17).In order better to characterize the toxic derivatives and their biological properties, relatively pure methyl linoleate was prepared, heated in the absence of air, then fractionated. The fractions were tested for intestinal absorption and deleterious action in the rat.Recently Kaunitz et al. (18) have made a similar study on thermal oxidation products of the same ester.

show abstract