A-linoleic acid

A Linoleic acid C Iso-oleic acid B cis-oleic acid D Stearic acid... 

Figure 10.7 Autoxidation of a linoleic acid ester. In step 1 the reaction is initiated by the attack of a radical on one of the hydrogen atoms of the -CH2-group between the two double bonds this hydrogen abstraction produces a radical that is a resonance hybrid. In step 2 this radical reacts with oxygen in the first of two chain-propagating steps to produce an oxygen-containing radical, which in step 3 can abstract a hydrogen from another molecule of the linoleic ester (Lin-H). The result of this second chain-propagating step is the formation of a hydroperoxide and a radical (Lin ) that can bring about a repetition of step 2.

N.A. Linoleic acid, linolenic acid, phenolics, flavonoids, tannins.103,118,152 Treat asthma, arteriosclerosis, multiple sclerosis, atopic eczema, schizophrenia, diabetic neuropathy, cardiovascular diseases, antitumor. 

N.A. Linoleic acid, palmitic acid, stearic acid, sitosterol, diosgenin, tigonenin, solanine, chaconine, solasodine, solasonine, solamargine.145 This herb is toxic. Remedy for tumors and cancer, diuretic, treat eye diseases, fevers, hydrophobia. It is laxative, emollient, anti-inflammatory. 

FIGURE 10.1 Schematic of the mechanisms of lipid peroxidation using a linoleic acid ester as a substrate. 

Carcinogenic aminoazo dyes were previously found to increase the latent period of linoleate peroxidation and that DAB was a more effective antioxidant than MAB (13). Furthermore, as autoxidation of the linoleic acid proceeded, N-demethylation of DAB and MAB occurred. Demethylation of DAB also occurred in vitro when DAB is dissolved in cottonseed oil and mixed with ground brown rice (14). Our results clearly indicate that a linoleic acid hydroperoxide-hematin system readily N-demethylates DAB to MAB and MAB to AB. Previously, it was found that in this system, HCHO formation by N-demethylation of DAB was faster than that obtained with MAB (15). Similar results are now reported during the H202 peroxidase catalyzed oxidation of DAB and MAB. Peroxidase and H2O2 have previously been reported to catalyze the N-dealkylation of other arylamines (16, 17). 

The average oil content of commercial com hybrids planted in the com belt has declined over the last 50 years from 4.8-5.0% to 4.4%.52 The apparent cause of this decline has been widespread use of one or two high yielding, low oil content corn inbreds. At the same time, the iodine value of com oil has increased from 122-124 to 128-130, equivalent to a linoleic acid content increase from 55% to 60%. This change is apparently associated with the decline in oil content.53... 

Jerusalem artichoke tubers contain little or no starch, virtually no fat, and have a relatively low calorific value. Of the small amount of fat present, trace amounts of monounsaturated and polyunsaturated fatty acids have been reported, but no saturated fatty acids (Whitney and Rolfes, 1999). The polyunsaturated fatty acids linoleic (18 2 cis, cis n-6) and a-linoleic acid (18 3 n-3) have been recorded as present at 24 mg and 36 mg-100 g 1 of raw tuber, respectively (Fineli, 2004). The tubers are a good source of dietary fiber, because of the presence of inulin. 

The hydrocarbon chains of fatty acids often contain one or more cis double bonds. These unsaturated lipids are especially prone to autoxidation. An example is provided by the following equation, which shows an autoxidation reaction of the ester of a-linoleic acid. Note that this is a chain reaction, so one initiator can cause numerous lipid molecules to be oxidized. 

Brodowsky, I. D., Hamberg, M., and Oliw, E. H. 1992. A Linoleic-Acid (8r)-Dioxy-genase and Hydroperoxide Isomerase of the Fungus Gaeumannomyces-Graminis. Biosynthesis of (8r)-Hydroxylinoleic Acid and (7s,8s)-Dihydroxylinoleic Acid from (8r)-Hydroperoxylinoleic Acid. J. Biol. Chem., 267, 4738-14745. 

Ahn, D, U., Wolfe, F. H., and Sim, J. S. (1S>95). Dietary a-linoleic acid and mixed toco-pherols, and packaging influences on lipid stability in broiler chicken breast and leg muscle. /. Food Sd. 60,1013-1018. 

Red wines have been shown to have higher antioxidant capacity than rose and white wines when analyzed by a linoleic acid peroxidation assay based on measuring chemiluminescence (Kondo et al., 1999). The higher antioxidant activity was related... 

In 1989, Hamanaka and coworkers isolated a new esterified cerebroside from human epidermis, and found it to be a linoleic acid-containing acylglucosylceramide (162, Figure 6.24). She later named 162 type I epidermoside, because it was specific to epidermis. Her works have been reviewed.35 The same structure... 

Lee, S.H., Oe, T., Arora, J.S., and Blair, I.A. (2005) Analysis of Fell-mediated decomposition of a linoleic acid-derived lipid hydroperoxide by liquid chroma-tography/mass spectrometry. J. Mass Spectrom., 40, 661-668. 

AI3-11132 CCRIS 650 EINECS 200-470-9 Emersol 310 Emersol 315 Extra Linoleic 90 FEMA No. 3380 Grape seed oil HSDB 5200 Linoleic acid a-Linoleic acid 9Z,12Z-Linoleic acid cis.cis-Linoleic acid 9-cis,12-cis-Linoleic acid Linolic acid NSC 281243 9,12-Octadecadienoic acid 9,12-Octadecadienolc acid (9Z,12Z)- 9,12-Octadecadienoic acid, (Z,Z)- (Z,Z)-9,12-Octadecadienoic acid Oils, grape Oils, grape seed Polylin 515 Polylin No. 515 Telfairic acid Unifac 6550. Unsaturated fatty acid used in manufacture of paints, coatings, emulsifiers, vitamins. Oil bpi = 230-232" d2 = 0.914 insoluble in H2O, soluble in organic solvents. Arizona CasChem Henkel/Emery Hercules Inc. Langley Smith Ltd. 

Kaneko, T., Honda, S., Nakano, S.I. and Matsuo, M. (1987) Lethal effects of a linoleic acid hydroperoxide and its autoxidation products, unsaturated aliphatic aldehydes on human diploid fibroblasts. Chem.-Biol. Interact. 63 127-137. 

Canola and soybean oil have a relatively high content of the essential fatty acid a-linoleic acid. 

It is good for health to ensure a steady supply of essential fatty acids such as a-linoleic acid. Since safflower oil has very little (or none according to the table) of this fatty acid, but sunflower oil has some, then sunflower oil would be the preferred choice, all other things being equal. 

The protocol In most of these published experimental studies involved feeding postweaned animals diets that contained high levels of fats, oils, or fat-oil mixtures. Diets with vegetable oils contain more than adequate amounts of essential fatty acids with a linoleic acid content from 7% in olive oil to over 70% in sunflower oil (Table I). The fatty acid composition of the animal body, including the heart, generally will reflect the dietary fatty acids (Carroll 1965 Holub and Kuksis, 1978). This in part may be due to the fact that the high levels of fat in the diet depress significantly the de novo synthe-... 

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