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Example of an unsaturated fat triglyceride. Left part: glycerol, right part from top to bottom: palmitic acid, oleic acid, alpha-linolenic acid, chemical formula: C₅₅H₉₈O₆

Triglyceride (help· info) (more properly known as triacylglycerol (help· info) or triacylglyceride) is glyceride in which the glycerol is esterified with three fatty acids.^[1] It is the main constituent of vegetable oil and animal fats. Image File history File links Fat_triglyceride_shorthand_formula. ... Image File history File links Fat_triglyceride_shorthand_formula. ... Glycerine, Glycerin redirects here. ... Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated fatty acids found in animals and plants. ... Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable sources. ... Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. ... Image File history File links Triglyceride. ... Image File history File links Triacylglycerol. ... Glycerides are esters of glycerol and fatty acids. ... Glycerine, Glycerin redirects here. ... For other uses, see Ester (disambiguation). ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... It has been suggested that this article or section be merged with cooking oil. ... Animal fats are fats obtained from animal sources, including: blubber cod liver oil lard (pork fat) tallow (beef fat) schmaltz (chicken fat) In human nutrition—as far as regions where heart disease is a more common cause of death than starvation are concerned—animal fats are often claimed to be...

Chemical structure

General structure of a triglyceride

The chemical formula is RCOO-CH₂CH(-OOCR')CH₂-OOCR", where R, R', and R" are long alkyl chains. The three fatty acids RCOOH, R'COOH and R"COOH can be all different, all the same, or only two the same. File links The following pages link to this file: Triglyceride Categories: Free use images | Compound images ... File links The following pages link to this file: Triglyceride Categories: Free use images | Compound images ... An alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ...

Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths but 16, 18 and 20 carbons are the most common. Natural fatty acids found in plants and animals are typically composed only of even numbers of carbon atoms due to the way they are bio-synthesised from acetyl CoA. Bacteria, however, possess the ability to synthesise odd- and branched-chain fatty acids. Consequently, ruminant animal fat contains odd numbered fatty acids, such as 15, due to the action of bacteria in the rumen. General Name, Symbol, Number Carbon, C, 6 Chemical series Nonmetals Group, Period, Block 14 (IVA), 2, p Density, Hardness 2267 kg/m3 0. ... Acetyl-CoA is an important molecule in metabolism, used in many biochemical reactions. ... It has been suggested that this article or section be merged with Ruminantia. ... Phyla Actinobacteria Aquificae Chlamydiae Bacteroidetes/Chlorobi Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Lentisphaerae Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Verrucomicrobia Bacteria (singular: bacterium) are unicellular microorganisms. ... The rumen, also known as the fardingbag or paunch forms the larger part of the reticulorumen, which is the first chamber in the alimentary canal of ruminant animals. ...

Most natural fats contain a complex mixture of individual triglycerides; because of this, they melt over a broad range of temperatures. Cocoa butter is unusual in that it is composed of only a few triglycerides, one of which contains palmitic, oleic and stearic acids in that order. This gives rise to a fairly sharp melting point, causing chocolate to melt in the mouth without feeling greasy. Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated fatty acids found in animals and plants. ... Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable sources. ... Stearic acid (IUPAC systematic name: octadecanoic acid) is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. ... For other uses, see Chocolate (disambiguation). ...

Metabolism

See also fatty acid metabolism

Triglycerides, as major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice as much energy (9 kcal/g) as carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) (with the help of lipases and bile secretions), which are then moved into the cells lining the intestines (absorptive enterocytes). The triglycerides are rebuilt in the enterocytes from their fragments and packaged together with cholesterol and proteins to form chylomicrons. These are excreted from the cells and collected by the lymph system and transported to the large vessels near the heart before being mixed into the blood. Various tissues can capture the chylomicrons, releasing the triglycerides to be used as a source of energy. Fat and liver cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain can not utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose, via gluconeogenesis, for brain fuel when it is broken down. Fat cells may also be broken down for that reason, if the brain's needs ever outweigh the body's. This article or section is in need of attention from an expert on the subject. ... Very Low Density Lipoprotein (VLDL) is a lipoprotein subclass. ... Chylomicrons are large lipoprotein particles (having a diameter of 75 to 1,200nm) that are created by the absorptive cells of the small intestine. ... Structure of the coenzyme adenosine triphosphate, a central intermediate in energy metabolism. ... Etymology: French calorie, from Latin calor (heat), from calere (to be warm). ... Lactose is a disaccharide found in milk. ... A representation of the 3D structure of myoglobin, showing coloured alpha helices. ... In anatomy, the intestine is the segment of the alimentary canal extending from the stomach to the anus and, in humans and other mammals, consists of two segments, the small intestine and the large intestine. ... Lipolysis is the breakdown of fat stored in fat cells. ... A computer-generated image of a type of pancreatic lipase (PLRP2) from the guinea pig. ... Bile (or gall) is a bitter, yellow or green alkaline fluid secreted by hepatocytes from the liver of most vertebrates. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... Glucagon ball and stick model A microscopic image stained for glucagon. ... The human brain In animals, the brain (enkephalos) (Greek for in the skull), is the control center of the central nervous system, responsible for behavior. ... Glycerine, Glycerin redirects here. ... Glucose (Glc), a monosaccharide (or simple sugar), is an important carbohydrate in biology. ... Pyruvic acid Oxaloacetic acid Phosphoenolpyruvate Fructose 1,6-bisphosphate Fructose 6-phosphate Glucose-6-phosphate Glucose Gluconeogenesis is the generation of glucose from non-sugar carbon substrates like pyruvate, lactate, glycerol, and amino acids (primarily alanine and glutamine). ...

Unlike many other molecules, triglyceride can pass through cell membranes freely, as its non-polar molecular structure prevents it from reacting with the phospholipid bilayer membrane. In chemistry, a nonpolar compound is one that does not have concentrations of positive or negative electric charge. ... A DPPC bilayer simulation Color scheme: PO4 = green, N(CH3)3 = violet, water = blue, terminal CH3 = yellow, O = red, glycol C = brown, chain C = grey In biology and chemistry, a lipid bilayer is a membrane or zone of membrane composed only of lipid. ...

Role in disease

See also the main article hypertriglyceridemia

In the human body, high levels of triglycerides in the bloodstream have been linked to atherosclerosis, and, by extension, the risk of heart disease and stroke. However, the negative impact of raised levels of triglycerides is lower than that of LDL:HDL ratios. The risk can be partly accounted for by a strong inverse relationship between triglyceride level and HDL-cholesterol level. In medicine, hypertriglyceridemia (or Hypertriglyceridaemia) denotes high (hyper-) blood levels (-emia) of triglycerides, the most abundant fatty molecule in most organisms. ... Coronary heart disease (CHD), also called coronary artery disease (CAD), ischaemic heart disease, atherosclerotic heart disease, is the end result of the accumulation of atheromatous plaques within the walls of the arteries that supply the myocardium (the muscle of the heart) with oxygen and nutrients. ... For other uses, see Stroke (disambiguation). ...

Another disease caused by high triglycerides is pancreatitis. Pancreatitis is inflammation of the pancreas. ...

Guidelines

The American Heart Association has set guidelines for triglyceride levels:^[2] The American Heart Association (AHA) is a non-profit organization in the United States that fosters appropriate cardiac care in an effort to reduce disability and deaths caused by cardiovascular disease and stroke American Stroke Association Web site. ...

Please note that this information is relevant to triglyceride levels as tested after fasting. Triglyceride levels remain temporarily higher for a period of time after eating. The milligram (symbol mg) is an SI unit of mass. ... A decilitre (or deciliter), abbreviated dL or dl, is one tenth of a litre, or 1×10−4 m3, or 100 millilitre. ... The mole (symbol: mol) is the SI base unit that measures an amount of substance. ... The litre or liter (see spelling differences) is a unit of volume. ... Fasting is primarily the act of willingly abstaining from some or all food, drink, or both, for a period of time. ...

Reducing triglyceride levels

Moderating the consumption of fats and carbohydrates and aerobic exercise are essential to reducing triglyceride levels. Omega-3 fatty acids from fish, flax seed oil, or other sources (up to 3g per day, unless under physician care)^[3], Omega-6 fatty acids, one or several grams of niacin (mega-dose vitamin B-3) per day and some statins reduce triglyceride levels. Fibrates have been used in some cases as some fibrates can bring down TGs substantially. However they are not used in first line as they can have unpleasant or dangerous side effects. In one case due to an increase in mortality, clofibrate was withdrawn from the North American market. Alcohol abuse can cause elevated levels of triglycerides. Omega-3 fatty acids are polyunsaturated fatty acids found in certain fish tissues, and in vegetable sources such as flax seeds, walnuts, and canola oil. ... Dietary sources of omega-6 fatty acids include: cereals whole-grain breads margarine most vegetable oils eggs and poultry baked goods. ... Niacin, also known as nicotinic acid or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair. ... Lovastatin, the first statin to be marketed The statins (or HMG-CoA reductase inhibitors) form a class of hypolipidemic agents, used as pharmaceutical agents to lower cholesterol levels in people with or at risk for cardiovascular disease. ... In pharmacology, the fibrates are a class of amphipathic carboxylic acids. ...

Industrial uses

Triglycerides are also split into their components via transesterification during the manufacture of biodiesel. The fatty acid monoalkyl ester can be used as fuel in diesel engines. The glycerin has many uses, such as in the manufacture of food and in the production of pharmaceuticals. Other examples are the Triglyceride_process in the decaffeination of coffee beans. In organic chemistry, transesterification is the process of exchanging the alkoxy group of an ester compound by another alcohol. ... This article is about transesterified plant and animal oils. ... An alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... For other uses, see Ester (disambiguation). ... A diesel engine built by MAN AG in 1906 Rudolf Diesels 1893 patent on his engine design A Diesel engine is an internal combustion engine which operates using the Diesel cycle. ... Decaffeination is the act of removing caffeine from coffee beans and tea. ...

Staining

Staining for fatty acids, triglycerides, lipoproteins, and other lipids is done through the use of lysochromes (fat-soluble dyes). These dyes can allow the qualification of a certain fat of interest by staining the material a specific color. Some examples: Sudan IV, Oil Red O, and Sudan Black B. A lysochrome is a soluble dye used for biochemical staining of triglycerides, fatty acids, and lipoproteins. ... Sudan IV Sudan IV (C24H20N4O) is a lysochrome (fat-soluble dye) diazo dye used for staining of lipids, triglycerides and lipoproteins on frozen paraffin sections. ... Oil Red O Oil Red O (Solvent Red 27, Sudan Red 5B, C.I. 26125, C26H24N4O) is a lysochrome (fat-soluble dye) diazo dye used for staining of neutral triglycerides and lipids on frozen sections and some lipoproteins on paraffin sections. ... Sudan Black B Sudan Black B (C26H24N4O) is a lysochrome (fat-soluble dye) diazo dye used for staining of neutral triglycerides and lipids on frozen sections and some lipoproteins on paraffin sections. ...

References

1. ^ Nomenclature of Lipids. IUPAC-IUB Commission on Biochemical Nomenclature (CBN). Retrieved on 2007-03-08.
2. ^ http://www.americanheart.org/presenter.jhtml?identifier=183
3. ^ Fish and Omega-3 Fatty Acids. American Heart Association.

Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 67th day of the year (68th in leap years) in the Gregorian calendar. ...

See also

• Diglyceride acyltransferase - enzyme responsible for triglyceride biosynthesis
• Medium chain triglycerides