Oleic acid Monounsaturated fatty acids

Monounsaturated fatty acids have a single carbon-carbon double bond present in the chain, and polyunsaturated fatty acids have more than one carbon-carbon double bond. Oleic... 

Monounsaturated fatty acid fatty acid with one double bond (e.g., oleic acid). 

This is a heavier oil used in soaps and cosmetics but less favoured for massage unless blended with less viscous oils. It is traditionally used as a culinary oil, with many researched beneficial health effects due to the high level of monounsaturated fatty acids. Fatty acid composition is oleic (75.5%), palmitic (11%), linoleic (8%), stearic (2.7%), palmitoleic (1.2%) and linolenic (0.7%). 

Monounsaturated fatty acids. The report that monounsaturated fatty acids (viz., oleic acid) were just as effective as polyunsaturated fatty acids (viz., linoleic acid) in lowering plasma total and low-density lipoprotein (LDL) cholesterol (100) aroused interest in the nutritional properties of canola oil. Canola oil contains 60% oleic acid and is second only to olive oil, among the common vegetable oils, in oleic acid content. Although avocado oil and high-oleic sunflower oil also contain high levels of oleic acid (>70%), they are minor constituents in the average diet. 

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). 

The seeds of M. oleifera variety Mbololo yielded 26%, 31%, and 36% crude oil by cold-pressing, hexane extraction, and chloroform-methanol extraction (1 1, v/v), respectively (70). The seed oil was rich in total monounsaturated fatty acids and contained 74—75% oleic acid (Table 9). The total saturated fatty acids were... 

Monounsaturated fatty acids (MUFA) A fatly acid molecule that contains only one double bond along the carbon chain. Oleic acid (18 ln-9) is the most common monounsaturated fatty acid. All plants and animals, including humans, can synthesize oleic acid. 

FIGURE 17-9 Oxidation of a monounsaturated fatty acid. Oleic acid, as oleoyl-CoA (A ), is the example used here. Oxidation requires an additional enzyme, enoyl-CoA isomerase, to reposition the double bond, converting the cis isomer to a trans isomer, a normal intermediate in j8 oxidation. 

It has been now recognised that die phenolic profile of the foods, along with high intakes of the monounsaturated fatty acids, as oleic acid mainly, confers its health-promoting properties to die Mediterranean diet. In fact, olive oil is the main source of unsaturated acids and polyphenols that constitute a complex mixture in olive fruits and in its derived products. In addition, in O. europaea fruits, phenolic profile and content are important factors to consider in order to evaluate virgin olive oil quality. To remain that they are also partly responsible for autoxidation stability and organoleptic characteristics of olive oil. 

The conversion of a monounsaturated fatty acid to acetyl-GoA requires a reaction that is not encountered in the oxidation of saturated acids, a cis-trans isomerization (Figure 21.9). Successive rounds of P-oxidation of oleic acid (18 1) provide an example of these reactions. The process of P-oxidation gives rise to unsaturated fatty acids in which the double bond is in the trans arrangement, whereas the double bonds in most naturally occurring fatty acids are in the cis arrangement. In the case of oleic acid, there is a cis double bond between carbons 9 and 10. Three rounds of P-oxidation produce a 12-carbon unsaturated fatty acid with a cis double bond between carbons 3 and 4. The hydratase of the P-oxidation cycle requires a trans double bond between carbon atoms 2 and 3 as a substrate. A cis-trans isomerase produces a trans double bond between carbons 2 and 3 from the cis double bond between carbons 3 and 4. From this point forward, the fatty acid is metabolized the same as for saturated fatty acids. When oleic acid is P-oxidized, the first step (fatty acyl-GoA dehydrogenase) is skipped, and the isomerase deals with the cis double bond, putting it into the proper position and orientation to continue the pathway. 

Safflower oil is flavorless and colorless, and is nutritional. It is used mainly as a cooking oil and for the production of margarine. It may also be taken as a nutritional supplement." " There are two types of safflowers that produce different kinds of oil, one high in monounsaturated fatty acids (oleic acid) and the other high in polyunsaturated fatty acids (linoleic acid)." Normally, it is a linoleic-rich oil (about 75% linoleic acid) with LLL (47%), LLO (19%), and LLS (18%) as the major triacylglycerols. Safflower oil rich in oleic acid (about 74%) has also been developed (Saffola).46... 

Although nuts are high in fat, over 75% of the fat is unsatuiated, predominantly monounsaturated fatty acids (MUFA). For every lOOg of fat in macadamia nuts, 77.4% is MUFA, of which 58.5% is oleic acid (18 lo)9) and 18.7% is palmitoleic acid (16 1). While the hazelnut has the highest total MUFA content (83.1%), macadamias contain the highest levels of 16 1. Only 4.4% of the Upid content of macadamia nuts is composed of polyunsaturated fatty acids (PUFA), of which 2.6% is... 

Olive oil is a good example of a lipid that provides numerous health benefits when included in the diet. The main type of lipid found in all types of olive oil is monounsaturated fatty acids, or MUFAs, with the 18-carbon oleic acid being the predominant component (see Table 8.1 for its formula). MUFAs are considered to be healthy lipids. There is evidence that dietary MUFAs help lower total cholesterol levels in the body, and especially the levels of undesirable low-density lipoproteins (LDLs). Some research results show that MUFAs may help maintain normal blood clotting and normal blood pressure and may aid in the control of blood sugar levels. 

The reaction of excess amounts of methyl acrylate and the self-metathesis products of monounsaturated fatty acids like methyl ester of oleic acid with ethylene, produces valuable monomers for polycondensation polymers, as well as precursors for detergents in the presence of a suitable metathesis catalyst. In oleochemistry, azaleic and pelargonic acid were obtained industrially by ozonolysis of oleic acid. Non-linear fatty acid derivatives with two double bonds, (ricinoleic acid maleate) and one double bond (ricinoleic acid succinate) were produced from ricinoleic acid by esterification with maleic and succinic anhydride, respectively. Hydrogenation of this ricinoleic acid succinate yielded 12-hydroxystearic acid succinate which is a monomer for vegetable oil-based polyester. 

Menendez, J. A. Lupu, R. (2006). Mediterranean dietary traditions for the molecular treatment of human cancer anti-oncogenic actions of the main olive oil s monounsaturated fatty acid oleic acid (18 ln-9). Current Pharmaceutical Biotechnology, 7(6), 495-502. 

Linoleic acid is found in soybean, safflower and com oil, nuts, seeds, and some vegetables. a-Linolenic acid is found in flaxseeds, walnuts, and their oils canola oil is also a good source of a-linolenic acid. Edible oils rich in monounsaturated fatty acids are stable, flavorful, and nutritious for humans and animals. Oleic acid-rich soybean oil is more resistant to degradation by heat and oxidation and requires little... 

Upon expression the seeds yield about 50% (by weight) of a liquid wax composed of high molecular weight C20 and C22 esters of straight long-chain, monounsaturated fatty acids and alcohols (up to 85% of the oil), including monoethylenic acids composed mainly of eicosenoic acid (34%) and docose-noic acid (14%) alcohols, including eicose-nol (22%) and docosenol (21%) trace amounts of oleic and palmitoleic acids. 

Olive oil, which is the principal source of fat in the Mediterranean region, possesses a high content in monounsaturated fatty acids. Oleic acid, its main component, accounts for 55%—83% (mean 75%) of total fatty acids in it. 

The olive tree (Olea europa) has been cultivated for thousands of years. The oil is the most important constituent, but olives also contain phenolics, including vanillic acid, ferulic acid, the flavones luteolin and apigenin together with substantial amounts of the glucos-ide, oleuropein (Figure 7.35), which is bitter and is commonly neutralized by treatment with caustic soda before the olives can be eaten. Olives contain up to 40% oil of which, typically, three quarters is a monounsaturated fatty acid oleic acid (CIS 1), 14% saturated fatty acid (mainly palmitic acid, C16 0) and 9% polyunsaturated fatty acids. Ohve oil is... 

Several lines of evidence suggest that oxidatively modified LDL plays an important role in the development of atherosclerosis. Oxidative modification of LDL involves peroxidation of PUFAs. LDL particles enriched in PUFAs have been shown to be more susceptive to oxidative modification compared to LDL particles rich in monounsaturated fatty acids. Others have also suggested that a diet high in PUFAs may overwhelm the antioxidant defenses of cells. In particular, studies have shown that LA-enriched LDL is more prone to in vitro oxidation than oleic acid-enriched LDL. Concern also remains with... 

In comparison with the effects of oleic and linoleic fatty acids, Cig monounsaturated trans fatty acids raise LDL cholesterol and lower HDL cholesterol levels. 

Some natural edible oils contain, in addition to the widely occurring monounsaturated fatty acid, oleic acid, appreciable quantities of monounsaturated acids with 20 or 22 carbon atoms. Biochemically, these are usually formed by elongation of oleic acid, so that the double bonds are in positions 11 and 13 respectively. Examples are gadoleic acid cis-11-20 1) in certain fish oils and erucic acid (cw-13-22 l. Table 3.2), characteristic of seed oils in the plant family Cruciferae. Herring oil also... 

More than LOO different fatty acids are known, and about 40 occur widely. Palmitic acid (C ) and stearic acid (Cjy) are the most abundant saturated fatty adds oleic and linoleic acids (both Care the most abundant unsaturated ones. Oleic acid is monounsaturated since it has only one double bond, whereas linoleic, linolenic, and arachidonic acids are polyunsaturated fatty acids because they have more than one double bond. Linoleic and linolenic... 

As mentioned earlier, both MCTs and LCTs are used in tube feeding products. Corn, soy, and safflower oils have been the mainstay sources of fat in these products, providing mainly co-6 polyunsaturated fatty acids (PUFAs). On the other hand, some newer EN products contain higher quantities of co-3 PUFAs from sources such as fish oil [i.e., docosahexenoic acid (DHA) and eicosapentenoic acid or (EPA)]. Still other formulas contain higher quantities of monounsaturated fatty acids from canola oil and high-oleic safflower or sunflower oils. The essential fatty acid (EFA) content (mainly linoleic acid) of EN... 

Oleic acid is one of the "monounsaturated fatty acids" that nutritionists talk about. (Fatty acids are acidic compounds that take their name from their origin in the decomposition of natural fats.)... 

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