Oleic acids, structure

Oleic acid, structure of, 1062 Oligonucleotide, 1114 synthesis of, 1114-1116 Olive oil, composition of, 1062 -otie. ketone name ending, 697 -otdtrile, nitrile name ending, 754 Optical activity, 294-296 measurement of, 295 Optical isomers. 297 Optically active, 295 Orbital. 4... 

Structure and Mechanism of Formation. Thermal dimerization of unsaturated fatty acids has been explaiaed both by a Diels-Alder mechanism and by a free-radical route involving hydrogen transfer. The Diels-Alder reaction appears to apply to starting materials high ia linoleic acid content satisfactorily, but oleic acid oligomerization seems better rationalized by a free-radical reaction (8—10). 

When the groups on either end of a double bond are the same or are structurally similar- to each other, it is a simple matter to describe the configuration of the double bond as cis or bans. Oleic acid, for example, a compound that can be obtained from olive oil, has a cis double bond. Cinnanaldehyde, responsible for the characteristic odor of cin-nfflnon, has a bans double bond. 

Fats can be either optically active or optically inactive, depending on their structure. Draw the structure of an optically active fat that yields 2 equivalents of stearic acid and 1 equivalent of oleic acid on hydrolysis. Draw the structure of an optically inactive fat that yields the same products. 

This study could be extended to the synthesis of iron nanoparticles. Using Fe[N(SiMe3)2]2 as precursor and a mixture of HDA and oleic acid, spherical nanoparticles are initially formed as in the case of cobalt. However, a thermal treatment at 150 °C in the presence of H2 leads to coalescence of the particles into cubic particles of 7 nm side length. Furthermore, these particles self-organize into cubic super-structures (cubes of cubes Fig. ) [79]. The nanoparticles are very air-sensitive but consist of zerovalent iron as evidenced by Mossbauer spectroscopy. The fact that the spherical particles present at the early stage of the reaction coalesce into rods in the case of cobalt and cubes in the case of iron is attributed to the crystal structure of the metal particles hep for cobalt, bcc for iron. 

Dimerization of unsaturated fatty acids, to. so-called dimer acids, is widely practised in industry, where acid-treated clays are invariably used as a catalyst. In the case of oleic acid the major products are dimers, trimers, and isosteric acid. Koster et al. (1998) have investigated the relative importance of the various acid sites as well as structural and textural parameters of montmorrilonite. The interlamellar space dominates the oleic acid dimerization and the active site is the tetrahedrol substitution site. 

Soaps are composed of sodium salts of various fatty acids. These acids include those with the general structure CH3-(CH2) -COOH where n = 6 (caprylic acid), 8 (capric acid), 10 (lauric acid), 12 (myristic acid), 14 (palmitic acid), and 16 (stearic acid). Oleic acid (CH3-(CH2)7-CH=CH-(CH2)7-COOH) and linoleic acid (CH3-(CH2)4-CH=CH- H2-CH=CH-(CH2)7-COOH) are also common soap ingredients. These sodium salts readily dissolve in water, but other metal ions such as Ca2+ and Mg2+ form precipitates with the fatty acid anions. For example, the dissolution of the sodium salt of lauric acid and the subsequent formation of a precipitate of the lauric acid anion with calcium ion is given by... 

Figure 13.16.3 The molecular structure of a triglyceride, a fatty acid based on the triester of oleic acid.

Figure 13.16.4 The molecular structure of the mixed fatty acid palmitodiolein, which is triglyercide of two esters of oleic acid and one of palmitic acid.

An example of the large variety of monomer structures present in poly(HAMCL) is given in Fig. 2. Also different degrees of unsaturation in poly(HAMCL) can be established relatively easily [3-5,34-39]. For example, the compositional data in Table 1 for the repeat units show that about 16% of the mono-unsaturated double bonds are incorporated when oleic acid is used as feedstock. When tall oil fatty acids are used, over 40 % of the subunits of the resulting poly(HAMCL) are mono- or di-unsaturated, while the total degree of unsaturation of the alkyl side chains of linseed oil-based PHA is even higher (>65%). Moreover, a substantial part (about 30%) of these unsaturated linseed oil-based poly(HAMCL) subunits have up to three double bonds present. 

A modified SILAR system has been used to grow CdSe in CdS/CdSe core shell semiconductor nanocrystals.12 A cadmium precursor solution, with CdO dissolved with oleic acid in octadecane, was injected onto the substrate, and the Se solution (Se powder dissolved with tributylphosphine in octadecane) was similarly injected. The temperature of the reaction solution was 185 °C. A CdS outer layer in the CdS/CdSe/CdS colloidal quantum wells was deposited by alternating injections of cadmium and sulfur both in octadecane solutions at 230-240 °C. These structures showed high PL quantum yields (20-40%), relatively narrow emission bands, and tunable emission colors from about 520 to 650 nm depending on the number of CdSe monolayers. 

SILAR has been used for the synthesis of CdS/ZnS coatings for CdSe quantum dots. The precursor solutions were prepared by dissolving CdO, ZnO, and S in oleic acid and octadecane. The final coating consisted of three layers of CdS and three additional layers of ZnS. The photonic band structure of the photonic crystal had a modifying influence on the photoluminescence of the embedded quantum dots.90... 

Figure 11.2 Structures of commonly occurring unsaturated fatty acids (i) oleic acid, C18 1 (ii) linoleic acid, C18 2 (iii) a-linolenic acid, C18 3.

Fatty acids are carboxylic acids, often with a long aliphatic tail (long carbon chains), which can be either saturated (all single bonds) or unsaturated. They are biosynthesized from two-carbon units (acetate, CH3COO ), and therefore usually have an even number of carbons with a range of C4 to C36, although Ci6 and Ci8 are dominant. Figure 7.7 shows the structure of octadecanoic acid (slearic acid, Ci8 o), c/.v-9-octadeccnoic acid (oleic acid, Ci8 i), and... 

Figure 7.7 Structures of some fatty acids and sterols found in archaeological residues. Upper compound octadecanoic acid (stearic acid, Ci8 0), middle compound ds-9-octadecenoic acid (oleic acid, C18 1), lower compound cholesterol.

Figure 4.22 (a) Stearic and oleic acid (b) glycerol and a triglyceride (c) the general structure of a glycerophospholipid and (d) the glycerophospholipid l-stearoyl-2-oleoyl-3-phosphatidylcholine. 

R. Lieckfeldt, J. Villalain, J.-C. Gomez-Fernandez, and G. Lee. Influence of oleic acid on the structure of a mixture of hydrated model stratum corneum fatty acids and their soaps. Colloids Surf. 90 225-234 (1994). 

The common fatty acids have a linear chain containing an even number of carbon atoms, which reflects that the fatty acid chain is built up two carbon atoms at a time during biosynthesis. The structures and common names for several common fatty acids are provided in table 18.1. Fatty acids such as palmitic and stearic acids contain only carbon-carbon single bonds and are termed saturated. Other fatty acids such as oleic acid contain a single carbon-carbon double bond and are termed monounsaturated. Note that the geometry around this bond is cis, not trans. Oleic acid is found in high concentration in olive oil, which is low in saturated fatty acids. In fact, about 83% of all fatty acids in olive oil is oleic acid. Another 7% is linoleic acid. The remainder, only 10%, is saturated fatty acids. Butter, in contrast, contains about 25% oleic acid and more than 35% saturated fatty acids. 

This finding has been replicated several times in clinical studies. Let me cite one example. In a careful metabolic study carried out in 1990, Mensink and Katan determined the plasma LDL/HDL ratio when 10% of the energy from oleic acid was replaced in the diet by either the corresponding trans fat or the corresponding saturated fatty acid, stearic acid. The resulting LDL/HDL ratios were 2.02 on the oleic acid diet, 2.34 on the stearic acid diet, and 2.58 on the trans fatty acid diet. This is one more example of the impact of small structural changes in molecules on their biological properties. 

This structure shows a triglyceride with three identical saturated fatty acids. Tripalmitin, in which all fatty acids are palmitic acid (n = 14), provides one example of a fat. Triolein is an oil containing only oleic acid moieties esterified to glycerol. In contrast to these two examples, it is by no means necessary that the three fatty acid groups be derived from only one fatty acid. For example, we might have a triglyceride that contains one saturated fatty acid, say palmitic acid, one monounsaturated fatty acid, say oleic acid, and one polyunsaturated fatty acid, perhaps arachidonic acid. 

Figure 5.1 The structure of a glycerophospholipid. A simple diagram showing the charges on the head group. In this struction, palmitic and oleic acids, provide the hydrophobic component of the phospholipids and choline (and four bases) and the phosphate group provide the hydrophilic head. The unsaturated fatty acid, oleic acid, provides a kink in the structure and therefore some flexibility in the membrane structure which allows for fluidity. The more unsaturated the fatty acid, the larger is the kink and hence more fluidity in the membrane. Cholesterol molecules can fill the gaps left by the kink and hence reduce flexibility. Hydroxyl groups on the bases marked are those that form phosphoester links. Choline and inositol may sometimes be deficient in the diet so that they are, possibly, essential micronutrients (Chapter 15).

Figure 11.10 Structure of ds-octadecenoic and trans-octadecenoic add (an example o/cis-trans isomerism). The common name for trans-octadecenoic acid is elaidic acid it is one of the few naturally occurring trans fatty acids. The common name for c/s-octadecenoic acid is oleic acid. Note that the two hydrocarbon chains are separated by the double bond which prevents rotation of the position of the two chains. The structure of the trans fatty acid is biochemically unusual and therefore biochemically excluded. ...

Figure 11.15 The reaction catalysed by lecithin cholesterol acyltransferase (LCAT). LinoLeate is transferred from a phospholipid in the blood to cholesterol to form cholesteryl linoleate, catalysed by LCAT. The cholesterol ester forms the core of HDL, which transfers cholesterol to the liver. Discoidal HDL (i.e. HDL3) is secreted by the liver and collects cholesterol from the peripheral tissues, especially endothellial cells (see Figure 22.10). Cholesterol is then esterified with lin-oleic acid and HDL changes its structure (HDL2) to a more stable form as shown in the lower part of the figure. R is linoleate.

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