Fatty acids saturated, table

Fats and oils may be synthesized in enantiomerically pure forms in the laboratory (30) or derived from vegetable sources (mainly from nuts, beans, and seeds), animal depot fats, fish, or marine mammals. Oils obtained from other sources differ markedly in their fatty acid distribution. Table 2 shows compositions for a wide variety of oils. One variation in composition is the chain length of the fatty acid. Butterfat, for example, has a fairly high concentration of short- and medium-chain saturated fatty acids. Oils derived from cuphea are also a rich source of capric acid which is considered to be medium in chain length (32). Palm kernel and coconut oils are known as lauric oils because of their high content of C-12 saturated fatty acid (lauric acid). Rapeseed oil, on the other hand, has a fairly high concentration of long-chain (C-20 and C-22) fatty acids. 

The lipid material precipitated upon mild acid treatment of the Boivin-extracted lipopolysaccharide is here termed a lipoidal precipitate. The fatty-acid profile (Table IV) of hydrolyzates of this material shows little variation between the seven lmmunotype strains. If the original lipopolysaccharides are first treated by phenol—water extraction, and the resultant materials then subjected to hydrolysis to release the lipid, the composition of the latter is significantly different it corresponds closely to the classic composition expected for lipid A. It is noteworthy that material extracted by the phenol—water (Westphal) method is rich in the Csaturated acid and in the hydroxy fatty acids having ten and twelve carbon atoms, whereas the and C g saturated acids present in the lipoidal precipitate, as prepared by the Boivin procedure, are absent or present at much lower levels in the lipid prepared by the Westphal procedure -9). It... 

Fatty acids consist of a hydrocarbon chain with a carboxylic acid at one end. They can be classified on the basis of the length of the hydrocarbon chain (Table 2.2) and whether there are any double bonds. Trivial names of fatty acids such as butyric, lauric, oleic and palmitic acids are in common use in the food industry. A form of short-hand is used to refer to triglycerides where POS is palmitic, oleic, stearic. If the chain length is the same an unsaturated fat will always have a lower melting point. Another classification of fats that is used is in terms of the degree of unsaturation of the fatty acids. Saturated fats are fats without any double bonds. Many animal fats are saturated, but some vegetable fats, e.g. coconut oil, are saturated also. Mono-unsaturated fats include oils like olive oil but also some partially hydrogenated fats. Polyunsaturated fats have many double bonds and include sunflower oil. Because they are... 

The enzyme system that catalyzes the synthesis of saturated long-chain fatty acids from acetyl CoA, malonyl CoA, and NADPH is called the fatty acid synthase. The constituent enzymes of bacterial fatty acid synthases are dissociated when the cells are broken apart. The availability of these isolated enzymes has facilitated the elucidation of the steps in fatty acid synthesis (Table 22.2). In fact, the reactions leading to fatty acid synthesis in higher organisms are very much like those of bacteria. 

The current interest in dietary fat, however, stems primarily from its implication in the origin of several chronic diseases. Interest has centered on both the amount and type of dietary fat in the development of cardiovascular disease, cancer, hypertension, and obesity. As a result, dietary recommendations in many countries call for a reduction in total fat intake, to 30% of energy, and in saturated fat intake, to less than 10% of energy. In addition, some nutrition recommendations specify recommended levels of n-6 and n-3 fatty acids in the diets. Hence, the source of fat in the diet has assumed considerable importance over the past few years. Interest in the nutritional properties of canola oil developed because of its fatty acid composition (Table 2). Canola oil is characterized by a low level of saturated fatty acids, a relatively high level of monounsaturated fatty acids, and an appreciable amount of the n-3 fatty acid ot-linolenic acid (18 3 n-3). 

Sunflower Fatty Acids Regular sunflower oil is characterized by a high concentration of linoleic acid, followed by oleic acid. Saturated fatty acids (mainly palmitic acid and stearic acid) do not amount to more than 15% of the fatty acid content. Table 1 shows the variation range of major fatty acids in regular sunflower oil (9, 20). 

TABLE 1. Principal n-3 Fatty Acids, Saturated, and Monoethylenic Fatty Acid Isomers (w/w%) in Triacylglycerols and Wax Esters of Copepods and Commercial Oils of Pelagic Species of North Atlantic Fish Likely to be Consuming Copepods. 

Fatty acid distribution Table 3.209 Major fatty acids in bacteria Saturated... 

Hydroxy fatty acids (HFAs) (Table 4) have hydroxyl functional groups attached to the principal chain, and they can be both saturated and unsaturated. The principal chain can be branched, and these branches are sometimes quite long. 

It is probable that our ancestors of several million years ago developed the characteristics leading to our modem biochemistry by eating animal fats (Crawford and Marsh, 1989 Sinclair and O Dea, 1990 O Dea, 1991). At first glance this should simplify discussion of animal fats, as shown by the basic fatty acids of Table 10.1. A popular shorthand notation is used to indicate the stmctures of common fatty acids. In the format x yn-z, x is the chain length or number of carbons in the chain, y is the number of methylene-interrupted cis ethylenic bonds and z is the inclusive number of carbon atoms from the terminal methyl group to the center of the nearest bond. As few as six fatty acids appear to adequately describe animal depot fats. Those fats listed are dominated by two fatty acids, 16 0 (palmitic) and 18 1 (oleic) add. Although tropical seed oils may be rich in C12-C18 saturated fatty adds (Elson, 1992), temperate oilseeds are rich in oleic acid and tend to include quantities of two fatty acids more unsaturated than oleic, especially 18 2n-6 (linoleic), and sometimes 18 3n-3 (linolenic). Even the original rapeseed (Brassica sp.) oil, with up to 50% of 22 ln-9 (emdc) acid usually had approximately 20% 18 2/1-6 and 10% 18 3/i-3 adds (Ackman 1983, 1990). 

Saturated and unsaturated hydrocarbons with odd and even numbers of carbon atoms in the molecule (about C11-C35) are present as the primary substances in all vegetable oils and animal fats. Alkanes, alkenes, alkadienes and alkatrienes also arise as oxidation products of unsaturated fatty acids, catalysed by lipoxygenases or by autoxidation of fatty acids during food storage and processing. Only the lower hydrocarbons can play a role as odour-active substances. The main hydrocarbons resulting from oxidation of unsaturated fatty acids are ethane from Hnolenic acid, pentane and butane from Hnoleic acid and hexane and octane from oleic acid. The immediate precursors of hydrocarbons are the fatty acid hydroperoxides (Table 8.4). The unsaturated hydrocarbons are predominantly (Z)-isomers. Numerous other hydrocarbons, including ahcycHc hydrocarbons, appear as secondary hpid oxidation products. 

Then, the saturated fatty acid percentage accused an increase atl50mM NaCl concentration. Similar changes have been found in triacylgycerols fatty acid composition (Table 2 because triacyglgycerols (TAG) in olive fruits constitute about 96% of total glycerolipids (Marzouk et Cherif, 1981). 

Cocoa butter raises total cholesterol concentrations to a lesser extent than palm oil. This difference in the serum cholesterol-raising potency of two fats high in saturated fatty acids (see Table 1) showed that not all saturated fatty acids have equal effects... 

Perhaps the most significant aspect of lipids in the human diet is their content of different types of fatty acids saturated, monounsaturated and polyunsaturated (section 3.1). It is important to point out at the outset that all natural fats contain complex mixtures of all three types of fatty acids. It is incorrect to describe a fat as saturated or polyunsaturated only the constituent fatty acids can be so described. Yet fats in which the saturated acids form the largest single fraction are frequently categorized as saturated fats to contrast them with fats in which polyunsaturated fatty acids predominate. As an example of where this can be misleading to a layman, lard is frequently categorized as a saturated fat, yet over half (about 55%) of the fatty acids are unsaturated (Table 4.1). 

Seed oils contain a wide variety of fatty acids, the composition of which is characteristic of the family to which the plant belongs. Generally one fatty acid predominates (Table 4.2). It may either be one of the normal fatty acids, palmitic, oleic, or linoleic, as exemplified by palm oil, olive oil and sunflower seed oil or it may be an unusual acid, for example erucic acid in older varieties of rape seed oil. Coconut oil and palm kernel oil are unusual among seed oils in having a preponderance of saturated fatty acids in which the acids of medium chain length predominate. It is therefore an unjustified generalization to characterize all vegetable oils as unsaturated. 

Table 9. UOP Sorbex Separation of Saturated and Unsaturated Tall Oil Fatty Acids...

Typically, soHd stabilizers utilize natural saturated fatty acid ligands with chain lengths of Cg—C g. Ziac stearate [557-05-1/, ziac neodecanoate [27253-29-8] calcium stearate [1592-23-0] barium stearate [6865-35-6] and cadmium laurate [2605-44-9] are some examples. To complete the package, the soHd products also contain other soHd additives such as polyols, antioxidants, and lubricants. Liquid stabilizers can make use of metal soaps of oleic acid, tall oil acids, 2-ethyl-hexanoic acid, octylphenol, and nonylphenol. Barium bis(nonylphenate) [41157-58-8] ziac 2-ethyIhexanoate [136-53-8], cadmium 2-ethyIhexanoate [2420-98-6], and overbased barium tallate [68855-79-8] are normally used ia the Hquid formulations along with solubilizers such as plasticizers, phosphites, and/or epoxidized oils. The majority of the Hquid barium—cadmium formulations rely on barium nonylphenate as the source of that metal. There are even some mixed metal stabilizers suppHed as pastes. The U.S. FDA approved calcium—zinc stabilizers are good examples because they contain a mixture of calcium stearate and ziac stearate suspended ia epoxidized soya oil. Table 4 shows examples of typical mixed metal stabilizers. 

Chemical Composition. Wool wax is a complex mixture of esters of water-soluble alcohols (168) and higher fatty acids (169) with a small proportion (ca 0.5%) of hydrocarbons (170). A substantial effort has been made to identify the various components, but results are compHcated by the fact that different workers use wool waxes from different sources and employ different analytical techniques. Nevertheless, significant progress has been made, and it is possible to give approximate percentages of the various components. The wool-wax acids (Table 9) are predominantiy alkanoic, a-hydroxy, and CO-hydroxy acids. Each group contains normal, iso, and anteiso series of various chain length, and nearly all the acids are saturated. 

Unsaturation in a fatty acid increases its solubihty in organic solvents, and the differences in solubiHties between saturated and unsaturated acids can be used to separate these acids (Table 9). 

Table 3. Saturated Fatty Acid Production and Disposition, 10 t...

Properties are furthermore determined by the nature of the organic acid, the type of metal and its concentration, the presence of solvent and additives, and the method of manufacture. Higher melting points are characteristics of soaps made of high molecular-weight, straight-chain, saturated fatty acids. Branched-chain unsaturated fatty acids form soaps with lower melting points. Table 1 Hsts the properties of some soHd metal soaps. 

Saturated fatty acids may be envisaged as based on acetic acid (CId3—COOH) as the first member of the series in which —CHj— is progressively added between the terminal CHj— and —COOH groups. Examples are shown in Table 14-1. Other higher members of the series are known to occur, particularly in waxes. A few branched-chain fatty acids have also been Isolated from both plant and animal sources. 

Tall oil fatty acids consist of resin acids (25% to 30%) and of a mixture of linolic acid, conjugated Cig fatty acids (45% to 65%), oleic acid (25% to 45%), 5,9,12-octadecatrienic acid (5% to 12%), and saturated fatty acids (1% to 3%). Resin acids are abietinic acid, dehydroabietic acid, and others. Properties of fatty acids are shown in Table 6-1. 

The major components have been identified tentatively as phenolic and fatty acids. At this time, seven phenolics have been identified in only four of the fractions. These are shown in Table III. A measure of the magnitude of the confidence level (cc) with a spectrum of standards is given. The first three entries are from the sunflower the last, from the Jerusalem artichoke. In all fractions isolated, both from the sunflower and the Jerusalem artichoke, a homologous series of fatty acids ranging from Cjo to Ci8 have been identified also by GC-MS. Even-chain, Cj6 to Cjs saturated and Cxs mono- and di-unsaturated, predominated. This is not surprising, since fatty acids are major constituents of plant... 

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