Major fatty acids lauric

The other food products (ingredients), which are subject to lipolyzed OF are the tropical oils, most notably coconut oil. Coconut oil contains lauric acid (Cl2) as a major fatty acid. Lauric acid tastes soapy when hydrolyzed from the triglyceride. While coconut does not contain a significant amount of lipases, coconut is often used in foods with other ingredients that do contribute lipases. It should be mentioned that lipases are reasonably heat stable enzymes. They will often survive a thermal treatment that one would expect to be adequate to denature the lipase. 

The lauric oils stand apart in the world of oils and fats. There are few of them, they move on their own higher price plateau and they do not mix comfortably with the common commodity oils and fats. There are only two lauric oils among the 17 major oils and fats in world commerce coconut oil (CNO) and palmkernel oil (PKO) (Oil World Annual 2001). They are called laurics because lauric acid (12 0) is the major fatty acid in these oils. The laurics are comprised of about 50% of lauric acid, while no other oil contains more than 1% (except butter fat, which contains about 3%). 

The major fatty acids in PKO are Cn (lauric acid) at about 48%, Cm (myristic acid) at about 16% and 18 1 (oleic acid) at about 15% (Codex 2001). No other fatty acid is present at more than 10%. The heavy preponderance of a single saturated fatty acid, combined with low levels of unsaturation, gives the oil its steep melting profile. 

Fig. 11. Genetic engineering of rapeseed oil. A high level of lauric acid was achieved by expressing a medium-chain acyl-ACP thioesterase (MCTE) from California Bay in the transgenic seeds. This enzyme intercepts the fatty acid synthesis pathway at 12 carbons and hydrolyzes the fatty acid from its ACP carrier. MoI% of major fatty acids in a typical canola cultivar are compared to the composition achieved through genetic engineering.

Vegetable oils according to their major fatty acid composition can be subclassified into laurics and oleics. Lauries comprise coconut oil and palm-kernel oil. Laurics mainly contain saturated C12 and C14 fatty acid triglycerides, the raw material basis for surfactants. Oleics mainly contain unsaturated Cie and Cig fatty acid triglycerides. Apart from food, which is the predominant use, they deliver lubricants and base oils, which can be used for energy generation, fuel, nutrition and specialty chemical derivatives. 

Although the number of fatty acids detected in plant tissues approaches 300, most of them only occur in a few plant species (Hitchcock and Nichols, 1971). The major fatty acids are all saturated or unsaturated monocarboxylic acids with an unbranched even-numbered carbon chain. The saturated fatty acids, lauric (dodecanoic), myristic (tetradecanoic), palmitic (hexadeca-noic), and stearic (octadecanoic), and the unsaturated fatty acids, oleic (cis-9-octadecenoic), linoleic (c/5 -9,cw-12-octadecadienoic), and linolenic (all-cij-9,12,15-octadecatrienoic (Table I), together account for almost all of the fatty acid content of higher plants. For example, about 94% of the total fatty acids of commercial oils and 89-97% of leaf fatty acids consist of these seven structures alone. It will be noted that the unsaturated acids all contain a cis-9 double bond and that the polyunsaturated acids contain a methylene-interrupted structure. The four saturated fatty acids differ from each other by two carbons. These structural relationships are due to the principal pathways of fatty acid biosynthesis in plants (see Stumpf, this volume. Chapter 7). 

Azima tetracantha is a flowering shrub that grows in India with a seed oil content of 12% (Daulatabad et al., 1991). Major fatty acids are linoleic (28.8%), linolenic acid (22%) and oleic acid (15.3%), with smaller amounts of palmitic (5.2%), myristic (4.2%), lauric (3.5%) and stearic (1.6%). This seed contains three unusual fatty acids ricinoleic (9.8%), malvalic (4.0%) and sterculic (5.6%). 

The GLC analysis of the fatty acid content was very similar to the Israeli variety with oleic acid (44.25%) as the major fatty acid followed by lauric (17.35%), myristic (11.45%), palmitic (10.3%) and linoleic acid (8.45%). Stearic acid (2.8%) and capric acid (2.78%) were present in low amounts. The degree of unsaturation was 52-54% (Sawaya et al., 1984). 

Many primary fatty amides which are available from various manufacturers are Hsted in Table 3. In 1986 approximately 55,000 metric tons of amides and bisamides were produced world wide (58), the majority of which are bisamides, followed in volume by primary amides. Most of these products are shipped in sohd form in bag or dmm quantities. Major producers of primary fatty amides are Akzo, Glyco, Humko, and Sherex. Bisamides are produced by Akzo, Milacron, and Syntex. There are over 100 producers of alkanolamides in the world, most of which are small specialized manufacturers to a specific industry. GAP, Henkel, Sherex, and Witco are among the principal producers. The most widely used alkanolamides are the Ai,Ai-bis(2-hydroxyethyl) fatty amides, mostly produced from middle-cut coco fatty acids (6% capryflc, 7% capric, 51% lauric, 19% myristic, 9% palmitic, and 2% stearic acids). An estimated 77,000 metric tons of alkanolamide was produced worldwide in 1986 (59). 

Using PTLC six major fractions of lipids (phospholipids, free sterols, free fatty acids, triacylglycerols, methyl esters, and sterol esters) were separated from the skin lipids of chicken to smdy the penetration responses of Schistosoma cercaria and Austrobilharzia variglandis [79a]. To determine the structure of nontoxic lipids in lipopolysaccharides of Salmonella typhimurium, monophosphoryl lipids were separated from these lipids using PTLC. The separated fractions were used in FAB-MS to determine [3-hydroxymyristic acid, lauric acid, and 3-hydroxymyristic acids [79b]. 

The traditional major source for the nonionic surfactant industry is fatty acid triglycerides from both animal and vegetable sources as the saturated or unsaturated acids. The saturated acids include lauric acid (w-dodecanoic), myristic acid (n-tetradecanoic), palmitic acid ( -hexadecanoic),and stearic acid (n-octadecanoic). The unsaturated acids include oleic acid (Z-9-octadecenoic) and linoleic acid (Z,Z-9,12-octadecadienoic). Of the 200 non-ionic surfactants... 

FIGURE 17-16 The fatty acids in the endoplasmic reticulum. This alternative to /3 oxidation begins with oxidation of the carbon most distant from the a carbon—the oj (omega) carbon. The substrate is usually a medium-chain fatty acid shown here is lauric acid (laurate). This pathway is generally not the major route for oxidative catabolism of fatty acids... 

Some Effects of Lipolysis. The most serious effect of lipolysis is the appearance of the so-called rancid flavor which becomes detectable in milk when the ADV exceeds 1.2-1.5 mEq/liter (Brathen 1980). The fatty acids and their soaps, which are thought to be implicated in the rancid flavor, have been studied in an effort to assess the role of the individual acids in the overall rancid flavor picture. Scanlan et al (1965) reported that only the even-numbered fatty acids from C4 to Cl2 account for the contribution of fatty acids to the flavor, but that no single acid exerts a predominating influence. Another study has implicated the sodium and/or calcium salts of capric and lauric acids as major contributors to the rancid flavor (Al-Shabibi, et al. 1964). Butyric acid, assumed to be the compound most intimately associated with the flavor, was not singled out in either study as being especially involved. 

For personal care applications, the major products in this group are amphoacetates or amphodiacetates , generally based on alkyl hydroxyethyl imidazolines from either a whole coconut fatty acid distribution or a lauric cut. The ampho portion of their name is a convention established by the International Nomenclature Committee for Cosmetic Products (INCI) to indicate that they are derived from imidazoline structures. The INCI nomenclature applied to these materials, amphoacetate and amphodiacetate, is intended to give an indication of the stoichiometry used to produce them, either 1 or 2 mol of sodium chloroacetate is added to each mole of fatty imidazoline. Modern analytical methods have been used to determine the structure of these products and almost all of them are actually monoacetates . The main difference between amphoacetates and ampho diacetates is the composition of the by-products. 

Palmitic and stearic acids are the major saturated fatty acid constituents of most animal and plant tissues. Much smaller amounts of other saturated fatty acids are present in most natural sources. Low concentrations of myristic acid (n-tetradecanoic acid 14 0) and lauric acid (n-dodecanoic acid 12 0) have been detected in certain tissues. 

Dates Phoenix dactylifera L.) are popular in most Middle Eastern countries and serve as a major source of food and nutrients (51, 52). Oil contents and fatty acid profiles of date seeds may vary among individual varieties. Date seeds contained 20-24% total fat (49). Oleic acid was the primary fatty acid in the date seed oil and had a concentration of 43.5 5% of total fatty acids. This was followed by lauric (12 0), myristic (14 0), palmitic (16 0), linoleic (18 2n6), capric (10 0), and stearic (18 0) acids along with trace amounts of other fatty acids (Table 7). Date seed oil may serve as an excellent dietary source of oleic acid with a minor amount of linoleic acid. 

Fatty Acids. A large volume of coconut fatty acids are used as major components in toilet soap manufacture. Its high lauric content provides the quick lathering properties of toilet soap. 

Data presented in previous sections revealed that the concentration of FFAs in plasma may reach 2.0 mM during exercise. How is this possible when the highest attainable concentration in water is only about 0,1 mM This problem was resolved by nature by use of albumin as a vehicle for the transport of FFAs within the circulation. Albumin constitutes about 60% of the protein of blood plasma. It is a major carrier of FFAs, other metabolites, hormones, and drugs- Serum albumin has the capadty to carry several fatty adds. Figure 4.45 shows results from an experiment usingpurificdalbumin.Thenumberoffattyacid molecules bound per protein molecule is plotted versus the concentration of unbound fatty acids in solution. The study, conducted with lauric acid (12 carbons) and myristic add (14 carbons), demonstrates that one protein molecule is able to bind at least 8 or 9 molecules of fatty acid. Albumin has a molecular weight of 69 kDa and occurs in human plasma at a concentration of about 0.6 mM (40 mg/ml) (Halliwell, 1988). 

As previously mentioned, the triglycerides found in biomass are esters of the triol, glycerol, and fatty acids (Fig. 3.6). These water-insoluble, oil-soluble esters are common in many biomass species, especially the oilseed crops, but the concentrations are small compared to those of the polysaccharides and lignins. Many saturated fatty acids have been identified as constituents of the lipids. Surprisingly, almost all the fatty acids that have been found in natural lipids are straight-chain acids containing an even number of carbon atoms. Most lipids in biomass are esters of two or three fatty acids, the most common of which are lauric (Cn), myristic (Cu), palmitic (Cia), oleic (Cis), and linoleic (Cis) acids. Palmitic acid is of widest occurrence and is the major constituent (35 to 45%) of the fatty acids of palm oil. Lauric acid is the most abundant fatty acid of palm-kemel oil (52%), coconut oil (48%), and babassu nut oil (46%). The monounsaturated oleic acid and polyunsaturated linoleic acid comprise about 90% of sunflower oil fatty acids. Linoleic acid is the dominant fatty acid in com oil (55%), soybean oil (53%), and safflower oil (75%). Saturated fatty acids of 18 or more carbon atoms are widely distributed, but are usually present in biomass only in trace amounts, except in waxes. 

TM for fatty acids derived from coconut oil. The major component acids are lauric andmyristic. They differ primarily in amount of unsaturated acid components and color. 

A note on health aspects is appropriate because the lauric oils are more than 80% saturated. This is much more than the major liquid oils such as soyabean, sunflower and rapeseed, which are respectively only 16%, 12% and 7% saturated. Nutritionally this may be thought of as a great disadvantage but such simple comparisons can be misleading. Lauric oils are only used in foods where a sharp melting hard fat is needed. When liquid oils are hydrogenated to a similar consistency, they contain not only more saturates but also trans fatty acids, which some recent studies have shown to be even more objectionable with regard to serum cholesterol profiles than the saturated ones (Byers 1997, Pietinen et al. 1998). 

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