Fat

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Fat as a nutrient

Template:Fats Fat is one of the three main macronutrients: fat, carbohydrate, and protein.[1] Fats are a wide group of compounds whose basis is in long-chain organic acids, called fatty acids. More particularly fats are esters of such organic acids formed with the alcohol glycerol. Glycerol is a triol, meaning that it has three chemically active -OH (hydroxyl) groups. Fats are made when each of these three -OH groups reacts with a fatty acid. The resulting fats are called triglycerides. Because of their preponderant aliphatic structure, fats are hydrophobic, generally soluble in organic solvents but generally insoluble in water. Fats made up of shorter chain fatty acids are usually liquid at room temperature, whereas the longer chain fats will be solid. Some ambiguity in terminology arises because the words "oil", "fat", and "lipid" are often used interchangeably. Of these lipid[2] is the general term, because a lipid is not necessarily a triglyceride. Oil is the term usually used to refer to fats that are liquids at normal room temperature, while fat is usually used to refer to fats that are solids at normal room temperature.

Fat is important foodstuff for many forms of life, and fats serve both structural and metabolic functions. They are necessary part of the diet of most heterotrophs (including humans). Some fatty acids that are set free by the digestion of fats are called essential because they cannot be synthesized in the body from simpler constituents. There are two essential fatty acids (EFAs) in human nutrition: alpha-linolenic acid (an omega-3 fatty acid) and linoleic acid (an omega-6 fatty acid).[2][3] Other lipids needed by the body can be synthesized from these and other fats. Fats and other lipids are broken down in the body by enzymes called lipases produced in the pancreas.

Fats and oils are categorized according to the number and bonding of the carbon atoms in the aliphatic chain. Fats that are saturated fats have no double bonds between the carbons in the chain. Unsaturated fats have one or more double bonded carbons in the chain. The nomenclature is based on the non-acid (non-carbonyl) end of the chain. This end is called the omega end or the n-end. Thus alpha-linolenic acid is called an omega-3 fatty acid because the 3rd carbon from that end is the first double bonded carbon in the chain counting from that end. Some oils and fats have multiple double bonds and are therefore called polyunsaturated fats. Unsaturated fats can be further divided into cis fats, which are the most common in nature, and trans fats, which are rare in nature. Unsaturated fats can be altered by reaction with hydrogen effected by a catalyst. This action, called hydrogenation, tends to break all the double bonds and makes a fully saturated fat. To make vegetable shortening, then, liquid cis-unsaturated fats such as vegetable oils are hydrogenated to produce saturated fats, which have more desirable physical properties e.g., they melt at a desirable temperature (30–40 °C), and store well, whereas polyunsaturated oils go rancid when they react with oxygen in the air. However, trans fats are generated during hydrogenation as contaminants created by an unwanted side reaction on the catalyst during partial hydrogenation. Consumption of such trans fats has shown to increase the risk of coronary heart disease[2][3]

Saturated fats can stack themselves in a closely packed arrangement, so they can solidify easily and are typically solid at room temperature. For example, animal fats tallow and lard are high in saturated fatty acid content and are solids. Olive and linseed oils on the other hand are unsaturated and liquid.

Fats serve both as as energy sources for the body, and as stores for energy in excess of what the body needs immediately. Each gram of fat when burned or metabolized releases about 9 food calories (37 kJ(oules)=8.8kal).[3] Fats are broken down in the healthy body to release their constituents, glycerol and fatty acids. Glycerol itself can be converted to glucose by the liver and so become a source of energy.

Trans (Elaidic acid) Cis (Oleic acid) Saturated (Stearic acid)
Elaidic acid is the principal trans unsaturated fatty acid often found in partially hydrogenated vegetable oils.[36] Oleic acid is a cis unsaturated fatty acid making up 55–80% of olive oil.[37] Stearic acid is a saturated fatty acid found in animal fats and is the intended product in full hydrogenation. Stearic acid is neither cis nor trans because it has no carbon-carbon double bonds.

Chemical structure

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File:Triglyceride Structural Formulae V.1.png
Example of a natural triglyceride with three different fatty acids. One fatty acids is saturated (blue highlighted), another contains one double bond within the carbon chain (green highlighted). The third fatty acid (a polyunsaturated fatty acid, highlighted in red) contains three double bonds within the carbon chain. All carbon-carbon double bonds shown are cis isomers.

There are many different kinds of fats, but each is a variation on the same chemical structure. All fats are derivatives of fatty acids and glycerol. The fat molecules are called triglycerides (triesters of glycerol). Three chains of fatty acid are bonded to each of the three -OH groups of the glycerol by the reaction of the carboxyl end of the fatty acid (-COOH) with the alcohol. HOH (water) is eliminated and the carbons are linked by an -O- bond through dehydration synthesis. This process is called esterification and fats are therefore ester|esters. As a simple visual illustration, if the kinks and angles of these chains were straightened out, the molecule would have the shape of a capital letter E. The fatty acids would each be a horizontal line; the glycerol "backbone" would be the vertical line that joins the horizontal lines. Fats therefore have "ester" bonds.

The properties of any specific fat molecule depend on the particular fatty acids that constitute it. Fatty acids form a family of compounds are composed of increasing numbers of carbon atoms linked into a zig-zag chain (hydrogen atoms to the side). The more carbon atoms there are in any fatty acid, the longer its chain will be. Long chains are more susceptible to intermolecular forces of attraction (in this case, van der Waals forces), and so the longer ones melt at a higher temperature (melting point).

Fatty acid chains differ by length, often categorized as short to very long.

  • Short-chain fatty acids (SCFA) are fatty acids with aliphatic tails of fewer than six carbons (i.e. butyric acid).[4]
  • Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6–12[5] carbons, which can form medium-chain triglycerides.
  • Long-chain fatty acids (LCFA) are fatty acids with aliphatic tails 13 to 21 carbons.[6]
  • Very long chain fatty acids (VLCFA) are fatty acids with aliphatic tails longer than 22 carbons

Any of these aliphatic fatty acid chains may be glycerated and the resultant fats may have tails of different lengths from very short triformin to very long, e.g., cerotic acid, or hexacosanoic acid, a 26-carbon long-chain saturated fatty acid. Long chain fats are exemplified by tallow (lard) whose chains are 17 carbons long. Most fats found in food, whether vegetable or animal, are made up of medium to long-chain fatty acids, usually of equal or nearly equal length. Many cell types can use either glucose or fatty acids for this energy. In particular, heart and skeletal muscle prefer fatty acids. Despite long-standing assertions to the contrary, fatty acids can also be used as a source of fuel for brain cells.

Importance for living organisms

Fats are also sources of essential fatty acids, an important dietary requirements. They provide energy as noted above. Vitamins A, D, E, and K are fat-soluble, meaning they can only be digested, absorbed, and transported in conjunction with fats.

Fats play a vital role in maintaining healthy skin and hair, insulating body organs against shock, maintaining body temperature, and promoting healthy cell function.

Fat also serves as a useful buffer towards a host of diseases. When a particular substance, whether chemical or biotic, reaches unsafe levels in the bloodstream, the body can effectively dilute—or at least maintain equilibrium of—the offending substances by storing it in new fat tissue. This helps to protect vital organs, until such time as the offending substances can be metabolized and/or removed from the body by such means as excretion, urination, accidental or intentional bloodletting, sebum excretion, and hair growth.

Adipose tissue

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The obese mouse on the left has large stores of adipose tissue. For comparison, a mouse with a normal amount of adipose tissue is shown on the right.

Template:Main In animals, adipose, or fatty tissue is the body's means of storing metabolic energy over extended periods of time. Adipocytes (fat cells) store fat derived from the diet and from liver metabolism. Under energy stress these cells may degrade their stored fat to supply fatty acids and also glycerol to the circulation. These metabolic activities are regulated by several hormones (e.g., insulin, glucagon and epinephrine).

The location of the tissue determines its metabolic profile: visceral fat is located within the abdominal wall (i.e., beneath the wall of abdominal muscle) whereas "subcutaneous fat" is located beneath the skin (and includes fat that is located in the abdominal area beneath the skin but above the abdominal muscle wall). Visceral fat was recently discovered to be a significant producer of signaling chemicals (i.e., hormones), among which several are involved in inflammatory tissue responses. One of these is resistin which has been linked to obesity, insulin resistance, and Type 2 diabetes. This latter result is currently controversial, and there have been reputable studies supporting all sides on the issue.

See also

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References

  1. United Kingdom The Food Labelling Regulations 1996Schedule 7: Nutrition labelling

Further reading

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Calories and Nutritional Information of Foods


Nutritional value of foods: UK Foods | US Foods | Dietary Supplements Portions of content adapted from Wikipedia's article on the same topic licensed under GNU FDL.

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