Triglycerides lauric acid

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... 

Palm kernel oil. The oil from pressing palm kernels contains triglycerides of stearic, myristic, oleic, palmitic, and lauric acids (the more common fatty acids) and is used in soap manufacture and as a dispersant and accelerator in polymerizations. 

Write a balanced equation for the condensation reaction in which lauric acid, palmitic acid, and stearic acid combine with glycerol to form a triglyceride. 

The wide availability of relatively inexpensive dimethylaminopropylamine (DMAPA) allows surfactant producers to convert economic triglycerides, fatty acids and methyl esters into amido -functional tertiary amines that may then be quaternized with sodium chloroacetate to produce alkylamidopropyl betaines (see Figure 6.15). The most economically significant of these is cocamidopropyl betaine which can be produced from a variety of feedstocks and lauramidopropyl betaine which is generally produced from lauric acid. These are widely used secondary surfactants in consumer products such as shampoos, bath products, washing up liquids and other cleaners. 

Oocoa butter (stearic fraction) contains about 33% oleic acid occupying the second position only. Consequently, positional specific lipases do not react with oleic acid. The Non-specificity Index (NSI) is based on the decline in oleic acid content in the triglycerides in relation to the lauric acid incorporation. A positional specific lipase will give a non-specificity index of 0 whereas a non-specific lipase will give a non-specificity index of 1. 

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. 

A number of plants and phytochemicals have attracted attention for their ability to reduce many of the risk factors associated with cardiovascular disease. Research into these diseases has shown the relationship between lesions, fatty streaking and plaque formation in blood vessels and the development of strokes and myocardial infarctions. These effects are linked to levels of plasma lipids which comprise triglycerides, cholesterol and other fat substances. It is known that the biosynthesis of lipids involves the condensation of several molecules of acetylcoenzyme A and malonylcoenzyme A in a gradual process of elongation of the fatty acid chain involving the sequential addition of two carbon units giving rise to fatty acids such as lauric acid (12 carbons) and eventually to palmitic acid (16 carbons). Palmitic acid is the precursor... 

A useful convention is to denote fatty acids by the number of carbon atoms and the number of C=C bonds. For example, lauric acid, which has 12 carbon atoms and no C=C bonds, is C12 0. This nomenclature does not specify the position of the C=C bonds, nor whether they are cis or trans. All fats are mixtures of triglycerides (and hence contain a number of different fatty acid residues). The approximate fatty acid composition of some fats is shown in Table 3.4. Butterfat contains a much wider range of fatty acids than the vegetable fats. Coconut oil contains very high levels of saturated fatty acids, particularly lauric acid. 

Dodecanedioic acid 1,12-Dodecanedioic acid. See Cl 2 dibasic acid Dodecanoic acid, diester with 1,2,3-propanetriol. See Glyceryl dilaurate Dodecanoic acid 1,2-ethanediyl ester. See Glycol dilaurate Dodecanoic acid 2-(2-hydroxyethoxy) ethyl ester. See PEG-2 laurate Dodecanoic acid, 2-hydroxypropyl ester. See Propylene glycol laurate Dodecanoic acid methyl ester. See Methyl laurate Dodecanoic acid, mixed triesters with octanoic acid, decanoic acid, and 1,2,3-propanetriol. See Captylic/capric/lauric triglyceride Dodecanoic acid, monoester with 1,2-propanediol. See Propylene glycol laurate... 

Caprylic/capric triglyceride PEG-4 esters Diisopropyl sebacate Isopropyl isostearate PEG-4 ditallate PEG-40 sorbitan peroleate PEG-20 sorbitan triisostearate PEG-100 stearate Stearyl stearate solubilizer, benzophenone Cetyl ricinoleate solubilizer, benzophenone-3 Dioctyl maleate Methyl acetyl ricinoleate Octyl palmitate Octyl salicylate solubilizer, biocides Cocamidopropyl hydroxysultaine N,N-Dimethyl-N-lauric acid-amidopropyl-N-(3-sulfopropyl)-ammonium betaine N,N-Dimethyl-N-myristyl-N-(3-sulfopropyl)-ammonium betaine N,N-Dimethyl-N-palmityl-N-(3-sulfopropyl)-ammonium betaine N,N-Dimethyl-N-stearyl-N-(3-sulfopropyl)-ammonium betaine... 

Caprylic/capric triglyceride PEG-4 esters DEA-laureth sulfate N,N-Dimethyl-N-lauric acid-amidopropyl-N-(3-sulfopropyl)-ammonium betaine N,N-Dimethyl-N-myristyl-N-(3-sulfopropyl)-ammonium betaine Dimethyl octynediol... 

A triglyceride was treated with sodium hydroxide to yield glycerol and three equivalents of sodium laurate (the conjugate base of lauric acid). Draw the structure of the triglyceride. 

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 fatty acid residues in triarachidin have more carbon atoms than the fatty acid residues in tristearin. Therefore, tiiarachadin is expected to have a higher melting point. It should be a solid at room temperature, and should therefore be classified as a fat, rather than an oil. Therefore, triglycerides made from lauric acid will also have a low melting point. 

The products of hydrolysis indicate that the starting triglyceride has three lauric acid residues, as shown ... 

The products of hydrolysis indicate that the starting triglyceride has two lauric acid residues and one palmitic acid residue. In order to be optically inactive, the palmitic acid residue must be connected to C2 of the glycerol backbone, as shown below. Otherwise, the highlighted position (C2 of the glycerol backbone) would be a chirality center ... 

Distillation. Most fatty acids are distilled to produce high quaHty products having exceUent color and a low level of impurities. Distillation removes odor bodies and low boiling unsaponifiable material in a light ends or heads fraction, and higher boiling material such as polymerized material, triglycerides, color bodies, and heavy decomposition products are removed as a bottoms or pitch fraction. The middle fractions sometimes can be used as is, or they can be fractionated (separated) into relatively pure materials such as lauric, myristic, palmitic, and stearic acids. 

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