Fat Trans Wikipedia

Trans fat is the common name for unsaturated fat with trans -isomer fatty acid(s). Trans fats may be monounsaturated or polyunsaturated but never saturated.

Unsaturated fat is a fat molecule containing one or more double bonds between the carbon atoms. Since the carbons are double-bonded to each other, there are fewer bonds connected to hydrogen, so there are fewer hydrogen atoms, hence "unsaturated". Cis and trans are terms that refer to the arrangement of chains of carbon atoms across the double bond. In the cis arrangement, the chains are on the same side of the double bond, resulting in a kink. In the trans arrangement, the chains are on opposite sides of the double bond, and the chain is straight.

The process of hydrogenation adds hydrogen atoms to cis -unsaturated fats, eliminating a double bond and making them more saturated. These saturated fats have a higher melting point, which makes them attractive for baking and extends shelf-life. However, the process frequently has a side effect that turns some cis-isomers into trans -unsaturated fats instead of hydrogenating them completely.

There is another class of trans fats, vaccenic acid, which occurs naturally in trace amounts in meat and dairy products from ruminants.

Unlike other dietary fats, trans fats are not essential, and they do not promote good health. The consumption of trans fats increases the risk of coronary heart disease by raising levels of "bad" LDL cholesterol and lowering levels of "good" HDL cholesterol. Health authorities worldwide recommend that consumption of trans fat be reduced to trace amounts. Trans fats from partially hydrogenated oils are more harmful than naturally occurring oils.

History

Nobel laureate Paul Sabatier worked in the late 1890s to develop the chemistry of hydrogenation which enabled the margarine, oil hydrogenation, and synthetic methanol industries. While Sabatier only considered hydrogenation of vapors, the German chemist Wilhelm Normann showed in 1901 that liquid oils could be hydrogenated, and patented the process in 1902. During the years 1905 – 1910 Normann built a fat hardening facility in the Herford company. At the same time the invention was extended to a large scale plant in Warrington, England, at Joseph Crosfield & Sons, Limited. It took only two years until the hardened fat could be successfully produced in the plant in Warrington, commencing production in the autumn of 1909. The initial year's production totalled nearly 3,000 tonnes. In 1909, Procter & Gamble acquired the US rights to the Normann patent; in 1911, they began marketing the first hydrogenated shortening, Crisco (composed largely of partially hydrogenated cottonseed oil). Further success came from the marketing technique of giving away free cookbooks in which every recipe called for Crisco.

Normann's hydrogenation process made it possible to stabilize affordable whale oil or fish oil for human consumption, a practice kept secret to avoid consumer distaste.

Prior to 1910, dietary fats primarily consisted of butterfat, beef tallow, and lard. During Napoleon’s reign in France in the early 1800s, a type of margarine was invented to feed the troops using tallow and buttermilk; it did not gain acceptance in the U.S. In the early 1900s, soybeans began to be imported into the U.S. as a source of protein; soybean oil was a by-product. What to do with that oil became an issue. At the same time, there was not enough butterfat available for consumers. The method of hydrogenating fat and turning a liquid fat into a solid one had been discovered, and now the ingredients (soybeans) and the “need” (shortage of butter) were there. Later, the means for storage, the refrigerator, was a factor in trans fat development. The fat industry found that hydrogenated fats provided some special features to margarines, which unlike butter, allowed margarine to be taken out of the refrigerator and immediately spread on a slice of bread. By some minor changes to the chemical composition of hydrogenated fat, they also found such hydrogenated fat provided superior baking properties compared to lard. Margarine made from hydrogenated soybean oil began to replace butterfat. Hydrogenated fat such as Crisco and Spry, sold in England, began to replace lard in the baking of bread, pies, cookies, and cakes in 1920.

In the 1940s Dr Catherine Kousmine researched the effects of trans fats on cancer.

Production of hydrogenated fats increased steadily until the 1960s as processed vegetable fats replaced animal fats in the US and other western countries. At first, the argument was a financial one due to lower costs; however, advocates also said that the unsaturated trans fats of margarine were healthier than the saturated fats of butter.

There were suggestions in the scientific literature as early as 1988 that trans fats could be a cause of the large increase in coronary artery disease. In 1994, it was estimated that trans fats caused 30,000 deaths annually in the US from heart disease.

In January 2007, faced with the prospect of an outright ban on the sale of their product, Crisco was reformulated to meet the United States Food and Drug Administration definition of "zero grams trans fats per serving" (that is less than one gram per tablespoon) by boosting the saturation and then cutting the resulting solid with oils. A University of Guelph research group has found a way to mix oils (such as olive, soybean and canola), water, monoglycerides and fatty acids to form a "cooking fat" that acts the same way as trans and saturated fats.

Chemistry

Chemically, trans fat refers to a lipid molecule that contains one or more double bonds in trans geometric configuration. A double bond may exhibit one of two possible configurations; trans or cis . In trans configuration, the carbon chain extends from opposite sides of the double bond, rendering a straighter molecule, whereas in cis configuration, the carbon chain extends from the same side of the double bond, rendering a bent molecule.

Fatty acids are characterized as either saturated or unsaturated based on the presence of double bonds in its structure. If the molecule contains no double bonds, it is said to be saturated; otherwise, it is unsaturated to some degree.

Only unsaturated fats can be trans fats . Saturated fatty acids are never trans fats because they have no double bonds, and therefore cannot display a trans - configuration. Moreover, lipids containing a triple bond (but no double bonds) cannot be trans fats because a triple bond can only assume one configuration.

Carbon atoms are tetravalent, forming four covalent bonds with other atoms, while hydrogen atoms bond with only one other atom. In saturated fatty acids, each carbon atom is connected to its two neighbour carbon atoms as well as two hydrogen atoms. In unsaturated fatty acids the carbon atoms that are missing a hydrogen atom are joined by double bonds rather than single bonds so that each carbon atom participates in four bonds.

Hydrogenation of an unsaturated fatty acid refers to the addition of hydrogen atoms to the acid, causing double bonds to become single ones as carbon atoms acquire new hydrogen partners (to maintain four bonds per carbon atom). Full hydrogenation results in a molecule containing the maximum amount of hydrogen (in other words the conversion of an unsaturated fatty acid into a saturated one). Partial hydrogenation results in the addition of hydrogen atoms at some of the empty positions, with a corresponding reduction in the number of double bonds. Commercial hydrogenation is typically partial in order to obtain a malleable mixture of fats that is solid at room temperature, but melts upon baking (or consumption).

In most naturally occurring unsaturated fatty acids, the hydrogen atoms are on the same side of the double bonds of the carbon chain ( cis configuration — meaning "on the same side" in Latin). However, partial hydrogenation reconfigures most of the double bonds that do not become chemically saturated, twisting them so that the hydrogen atoms end up on different sides of the chain. This type of configuration is called trans , which means "across" in Latin. The trans conformation is the lower energy form, and is favored when catalytically equilibriated as a side reaction in hydrogenation.

The same molecule, containing the same number of atoms, with a double bond in the same location, can be either a trans or a cis fatty acid depending on the conformation of the double bond. For example, oleic acid and elaidic acid are both unsaturated fatty acids with the chemical formula C 9 H 17 C 9 H 17 O 2 . They both have a double bond located midway along the carbon chain. It is the conformation of this bond that sets them apart. The conformation has implications for the physical-chemical properties of the molecule. The trans configuration is straighter, while the cis configuration is noticeably kinked as can be seen from the following three-dimensional representation.

The trans fatty acid elaidic acid has different chemical and physical properties owing to the slightly different bond configuration. Notably, it has a much higher melting point, 45 °C rather than oleic acid's 13.4 °C, due to the ability of t

Trans fat - Wikipedia, the free encyclopedia

Trans fat is the common name for unsaturated fat with trans-isomer fatty acid (s). Trans fats may be monounsaturated or polyunsaturated but never saturated.

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