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Next Page. Neutralization of fatty acids, i. Hydrogenation of unsaturated fatty acids is widely practiced. Typical conditions involve 2. This treatment affords saturated fatty acids.

The extent of hydrogenation is indicated by the iodine number. Hydrogenated fatty acids are less prone toward rancidification.

Since the saturated fatty acids are higher melting than the unsaturated precursors, the process is called hardening. Related technology is used to convert vegetable oils into margarine.

The hydrogenation of triglycerides vs fatty acids is advantageous because the carboxylic acids degrade the nickel catalysts, affording nickel soaps.

During partial hydrogenation, unsaturated fatty acids can be isomerized from cis to trans configuration.

More forcing hydrogenation, i. Fatty alcohols are, however, more easily produced from fatty acid esters. In the Varrentrapp reaction certain unsaturated fatty acids are cleaved in molten alkali, a reaction which was, at one point of time, relevant to structure elucidation.

Unsaturated fatty acids undergo a chemical change known as auto-oxidation. The process requires oxygen air and is accelerated by the presence of trace metals.

Vegetable oils resist this process to a small degree because they contain antioxidants, such as tocopherol.

Fats and oils often are treated with chelating agents such as citric acid to remove the metal catalysts. Unsaturated fatty acids are susceptible to degradation by ozone.

In chemical analysis, fatty acids are separated by gas chromatography of methyl esters; additionally, a separation of unsaturated isomers is possible by argentation thin-layer chromatography.

Short- and medium-chain fatty acids are absorbed directly into the blood via intestine capillaries and travel through the portal vein just as other absorbed nutrients do.

However, long-chain fatty acids are not directly released into the intestinal capillaries. Instead they are absorbed into the fatty walls of the intestine villi and reassemble again into triglycerides.

The triglycerides are coated with cholesterol and protein protein coat into a compound called a chylomicron. From within the cell, the chylomicron is released into a lymphatic capillary called a lacteal , which merges into larger lymphatic vessels.

It is transported via the lymphatic system and the thoracic duct up to a location near the heart where the arteries and veins are larger. The thoracic duct empties the chylomicrons into the bloodstream via the left subclavian vein.

At this point the chylomicrons can transport the triglycerides to tissues where they are stored or metabolized for energy. When metabolized, fatty acids yield large quantities of ATP.

Many cell types can use either glucose or fatty acids for this purpose. Fatty acids provided either by ingestion or by drawing on triglycerides stored in fatty tissues are distributed to cells to serve as a fuel for muscular contraction and general metabolism.

They are broken down to CO 2 and water by the intra-cellular mitochondria , releasing large amounts of energy, captured in the form of ATP through beta oxidation and the citric acid cycle.

Fatty acids that are required for good health but cannot be made in sufficient quantity from other substrates, and therefore must be obtained from food, are called essential fatty acids.

There are two series of essential fatty acids: one has a double bond three carbon atoms away from the methyl end; the other has a double bond six carbon atoms away from the methyl end.

Humans lack the ability to introduce double bonds in fatty acids beyond carbons 9 and 10, as counted from the carboxylic acid side.

These fatty acids are widely distributed in plant oils. The human body has a limited ability to convert ALA into the longer-chain omega-3 fatty acids — eicosapentaenoic acid EPA and docosahexaenoic acid DHA , which can also be obtained from fish.

Omega-3 and omega-6 fatty acids are biosynthetic precursors to endocannabinoids with antinociceptive , anxiolytic , and neurogenic properties.

Blood fatty acids adopt distinct forms in different stages in the blood circulation. They are taken in through the intestine in chylomicrons , but also exist in very low density lipoproteins VLDL and low density lipoproteins LDL after processing in the liver.

In addition, when released from adipocytes , fatty acids exist in the blood as free fatty acids. It is proposed that the blend of fatty acids exuded by mammalian skin, together with lactic acid and pyruvic acid , is distinctive and enables animals with a keen sense of smell to differentiate individuals.

Fatty acids are mainly used in the production of soap , both for cosmetic purposes and, in the case of metallic soaps , as lubricants. Fatty acids are also converted, via their methyl esters, to fatty alcohols and fatty amines , which are precursors to surfactants, detergents, and lubricants.

Esters of fatty acids with simpler alcohols such as methyl-, ethyl-, n-propyl-, isopropyl- and butyl esters are used as emollients in cosmetics and other personal care products and as synthetic lubricants.

Esters of fatty acids with more complex alcohols, such as sorbitol , ethylene glycol , diethylene glycol , and polyethylene glycol are consumed in food, or used for personal care and water treatment, or used as synthetic lubricants or fluids for metal working.

From Wikipedia, the free encyclopedia. Carboxylic acid. Main article: Saturated fat. For a more comprehensive list, see List of saturated fatty acids.

Main article: Unsaturated fat. Main article: Fatty acid synthesis. Main article: Rancidification. Main article: Fatty acid metabolism.

Main article: Essential fatty acid. Main article: Blood fatty acids. Fatty acid synthase Fatty acid synthesis Fatty aldehyde List of saturated fatty acids List of unsaturated fatty acids List of carboxylic acids Vegetable oil.

Pure and Applied Chemistry. International Union of Pure and Applied Chemistry. Retrieved Annales de Chimie , t. Recherches sur les corps gras d'origine animale.

Levrault, Paris, Chronological history of lipid center. Cyberlipid Center. Last updated on 11 November De Boeck, Bruxelles.

Lipids in Health and Disease. Nomenclature of Organic Chemistry. Recommendations, ". European Journal of Biochemistry.

Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. PLOS One. Bibcode : PLoSO.. Biochemistry 4th ed. New York: W. Freeman and Company.

Hormone Research. Fundamentals of Biochemistry 2nd ed. John Wiley and Sons. Uptake of valproic acid was reduced in the presence of medium-chain fatty acids such as hexanoate, octanoate, and decanoate, but not propionate or butyrate, indicating that valproic acid is taken up into the brain via a transport system for medium-chain fatty acids, not short-chain fatty acids.

Based on these reports, valproic acid is thought to be transported bidirectionally between blood and brain across the BBB via two distinct mechanisms, monocarboxylic acid-sensitive and medium-chain fatty acid-sensitive transporters, for efflux and uptake, respectively.

Monocarboxylate transporters MCTs are known to mediate the transport of short chain monocarboxylates such as lactate, pyruvate and butyrate.

MCT1 and MCT4 have also been associated with the transport of short chain fatty acids such as acetate and formate which are then metabolized in the astrocytes [78].

The Composition of Foods. Royal Society of Chemistry. Sundance Natural Foods. Department of Agriculture.

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