Oleic acid Subject

Separation of fatty acids (Ruthven, 1997). Tall oil from the pulp and paper industry is subjected to separation of rosin acid, linoleic acid, oleic acid, and neutral compounds. Distillation at reduced pressure is u.sed, but this leads to degradation of products. A Sorbex process eliminates this problem. 

K2. Kaplan, E., Edidin, B. D., Fruin, R. C., and Baker, L. A., Intestinal absorption of iodine 131 labelled triolein and oleic acid in normal subjects and in steatorrhea. Gastroenterology 34, 901-909 (1958). 

Infusion of fat into the ileum has been shown to cause a lengthening of the SITT—a phenomenon known as the ileal brake (27,28). However, the effect is generally modest (causing a delay of 30-60 min) and attempts to exploit this mechanism in drug delivery have had limited success. Dobson et al. (29,30) studied the effect of co-administered oleic acid on the small intestinal transit of non-disintegrating tablets. They showed a delay in SITT in over half of all cases, and a doubling of SITT in some instances, but in the other cases SITT was either unaffected or even reduced. Lin et al. (31) have also showed slowed GI transit in patients with chronic diarrhea by administration of emulsions containing 0, 1.6, and 3.2 g of oleic acid. Small intestinal transit in normal subjects was measured at 102 11 min, while the transit times in the patients treated with the three emulsions were, respectively, 29 3, 57 5 and 83 5 min. 

The purity of the purified triolein is verified as follows. According to standard procedures, replicate standard SPMDs are made using the purified triolein. The SPMDs are dialyzed and the dialysates are subjected to SEC fractionation. (Prior to SEC, dialysates should have <500 xg methyl oleate, and essentially no oleic acid.) The fractions collected from the SEC are evaluated by GC with ECD, FID, and MS. In order to pass the pre-use certification, the dialysate from a standard SPMD, after SEC, should contain less than 5 qg of methyl oleate, GC-ECD chromatograms... 

Giant vesicles have been the subject of several international meetings and specialized literature (Luisi and Walde, 2000 Fischer et al., 2000). There are several reasons for this interest. One is that, because of their size, they can be observed by normal optical microscopy, without using the much more expensive and indirect electron microscopy. Figure 10.7 shows, as an example, the transformations brought about by the addition of a water-insoluble precursor (oleic anhydride) to oleic acid giant vesicles (Wick et al., 1995). 

Analytical studies of the tergal secretions of male B. germanica have identified a number of volatile compounds, none of which has so far been subjected to behavioral assays on females. Brossut et al. (1975) found p-hydroxybenzyl alcohol, o-hydroxybenzyl alcohol, di- and tri-methylnaphthalene, benzothiazole, two isomers of nonyl phenol, and myristic, palmitic, and oleic acids. The fatty acids constituted > 92% of the volatile fraction given their abundance in feces and frass, and their role as putative aggregation pheromones (Wileyto and Boush, 1983 Fuchs et al., 1985 Wendler and Vlatten, 1993 Scherkenbeck et al., 1999),... 

Esters of the fatty acid oleic acid are components of membranes that are subject to autoxidation. Explain which hydrogens of an oleate ester you expect to be abstracted most readily by a radical. Show the structures of the major autoxidation products that would be formed from an oleate ester. 

The nature of OA interaction with SC lipids in vivo was of significant interest, particularly in light of the IR results above. Reflectance IR spectroscopy in conjunction with the use of a deuterated probe once again proved to be a valuable approach for the noninvasive evaluation of this enhancer in humans [153]. Prior to treatment, test sites on the inner ventral forearm of volunteers were cleansed with water, after which the subject remained at constant temperature and relative humidity, while three pretreatment spectra were collected. The experimental site on one arm was treated with a 5% v/v solution of perdeuterated oleic acid ( H-OA) in ethanol, while the control site, on the contralateral arm, was treated with ethanol alone. Both formulations were applied under occlusion for 16 hours posttreatment, the sites were swabbed clean with ethanol and then air-exposed for 2 hours to allow the occluded skin to dry. An ATR-IR spectmm of the dosed site was then obtained. This site was then tape stripped once and a second spectral examination was made. This sequential tape stripping and spectral acquisition was repeated -20 times in order to obtain an incremental spectral profile as a function of SC depth (defined by the cumulative weight of SC removed with tape stripping). IR spectra thus collected yielded the following information (a) the distribution... 

There, also, is interest in dietary monounsaturated fatty acids because of their possible protective effect against oxidation of LDL cholesterol (101). There is appreciable evidence that the uptake of LDL cholesterol and the formation of fatty streaks in the intima of large blood vessels, which is considered an early lesion of atherosclerosis, is enhanced by the oxidation of the LDL cholesterol (102, 103). LDL cholesterol was found to be appreciably more stable to oxidation when subjects were fed diets rich in oleic acid than when fed linoleic acid enriched diets (104-106). 

Canola oil is characterized by a low level of saturated fatty acids (less than 4% palmitic acid) and relatively high levels of oleic acid (60%) and a-linolenic acid (10%). It is second only to olive oil, among the common fats and oils, in oleic acid level and, except for soybean oil, the only common dietary fat that contains a significant amount of a-linolenic acid. Furthermore, there is a favorable balance in the levels of linolenic and linoleic acids (viz., 18 3/18 2 ratio of 1 2) in canola oil. Canola oil has been found equally as effective as soybean oil, safflower oil, and sunflower oil in reducing plasma total and LDL cholesterol levels in normolipi-demic subjects. It also was effective in reducing plasma total and LDL cholesterol levels in hyperlipidemic subjects when it replaced saturated fat in their diets. Canola oil diets also have been shown to affect the fatty acid composition of blood... 

With the elimination of saturated acids from the olive oil hydrolyzate by crystallization from acetone, the problem remaining in isolation of oleic acid is to remove the doubly unsaturated linoleic acid. Models and cylinders show that the introduction of just one cis double bond is enough to widen the molecule to the extent that it can no longer be inserted into the 14.3-cm wide channel which accommodates -alkanes (Fig. 1). However, amodel of 3-nonyne likewise fails to fit into the 14.3-cm channel, and the fact that this acetylenic hydrocarbon nevertheless forms a urea complex indicates that the channel is subject to some stretching, namely to a diameter of 16.2 cm, as in Fig. 2. 

MLS1 Malate synthase, enzyme of the glyoxylate cycle, involved in utilization of non-fermentable carbon sources expression is subject to carbon catabolite repression localizes in peroxisomes during growth in oleic acid medium... 

Thus, oleic acid, which contains eighteen carbon atoms, is converted by oxidation into two acids, each of which contains nine carbon atoms. As unsaturated compounds usually break at the double bond when subjected to active oxidation, the reaction given above is taken as evidence that in oleic acid this bond is situated as indicated by the structural formula given. In the oxidation the unsaturated carbon atoms are converted into carboxyl groups a monobasic acid and a dibasic acid, which contains two carboxyl groups, are thus obtained. Oleic acid, like other unsaturated compounds, reduces a dilute aqueous solution of potassium permanganate dihydroxystearic acid is formed —... 

Bore et al. [154] found that the structures of the Qg fatty acids of oily and dry hair differ. For subjects with dry hair, the predominant isomer is octadecenoic acid (oleic acid), whereas for subjects with oily hair 8-octadecenoic acid was the predominant isomer. Thus, oily hair is different from dry hair in its chemical composition and in its rheological character. 

When the data for all subjects were combined, palmitic acid (16 0) and oleic acid (18 ln-9) were inversely correlated with phase angle (Figs. 3 and 4). On the other hand, the three n-3 PUFA derived from 18 3n-3 (20 5n-3,22 5n-3, and 22 6n-3) were positively correlated with phase angle (Figs. 5,6 and 7). These same serum phospholipid fatty acids were also found to be significantly different between SCD subjects and controls (Table 2). The only fatty acid that was different in SCD sub-... 

Fig. 4. The relationship between phase angle and the weight percent of oleic acid (18 n-l) in serum phospholipids of subjects boys with sickle cell disease (SCD) ( ), control boys (O), girls with SCD (A), control girls (A) P< 0.001, r= 0.32.

All changes in fatty acid level, with the exception of llnoleic acid in the LEAR oil group, returned to pretest fat levels (day 10) with a return to the mixed fat diet for 8 days (day 32 to 39). As In other species (Walker, 1972), very little erucic acid was incorporated into serum phospholipids even though erucic acid comprised nearly 40% of the fat on the HEAR oil regimen. Fatty acid analyses of fat biopsies obtained from the middorsal abdomen of two of the subjects on the HEAR oil regimen on days 10 and 32 indicated that very little erucic acid was incorporated into adipose tissue. Erucic acid made up 0.4 and 2.0% of the total fatty acids of the two subjects on day 32. The low levels of erucic acid incorporated into phospholipids and triglycerides suggest that erucic acid is converted to other fatty acids, presumably oleic acid, in man as in other species. 

Orlistat (tetrahydrolipstatin) is a reversible inhibitor of oral, gastric, and pancreatic lipases. This inhibitor forms an ester linkage with serine (serine-152) in the active site of the lipase so that a decrease in the rate of lipid hydrolysis will occur [37]. Orlistat decreases the oral taste sensitivity to both oleic acid and triolein in obese subjects [38]. These results further suggest a role for lingual lipase in oral fat hydrolysis and detection. However, a conclusive role for human lingual lipase in oral fatty acid hydrolysis and detection still remains imclear at the present time [39]. 

Although increased levels of lipid peroxidation endproducts are found in most human diseases, the occurrence of lipid peroxidation does not always imply a state of disease. For example, increased levels of lipid peroxidation also occur in fasting human subjects, by the breakdown of fat (65). A certain level of lipid peroxidation may actually be expected after exposure to CIA, as most polyunsaturated fatty acids are more susceptible to the attack of oxygen radicals than monounsaturated fatty acids or saturated fatty acids (66). For example, supplementation with fish oil significantly increased plasma lipid peroxides in women (67, 68). Work by Banni et al. showed that CLA does not behave differently under oxidative stress than regular polyunsaturated fatty acids (51). The control oil used in the studies by Riserus et al. (35) and Basu et al. (64) was olive oil, which contains high levels of the monounsaturated acid oleic acid and has been shown to work as an anti-oxidant (69). 

The first work [64] described the synthesis of nonadecane-l,19-diol and tricosane-1,23-diol from oleic acid and erucic acid, respectively. For the synthesis of diacetals starting from diols and dimetoxymethane, use of 20 mol% methanesulfonic acid as a catalyst produced the desired 2,4,24,26-tetraoxaheptacosane from nonadecane-1,19-diol at 85% yield. Also, use of 20 mol% trifluoromethanesulfonic acid as a catalyst led to the formation of 2,4,28,30-tetraoxahentriacontane from tricosane-1,23-diol at 79% yield. Difunctional acetal monomers were then subjected to AMP at 80-100 "C, 2-4 mol% of p-toluenesulfonic acid as a catalyst, and reduced pressure to remove the dimethoxymethane byproduct. Authors obtained polymers with Mn values of 17 and 22 kDa, with the higher value arising from the longer-chain diol/diacetal. 

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