{{short description|Esters of three fatty acid chains and the alcohol glycerol, one of the three main macronutrients, also known as triglycerides}} {{pp-pc1}} {{pp|small=yes}} {{About|the type of nutrient in food|fat in humans and animals|Adipose tissue|other uses|Fat (disambiguation)}} {{sprotect2}} [[File:Trimyristin-3D-vdW.png|thumb|A molecule of a typical [[triglyceride]], the main type of fat. Note the three fatty acid chains attached to the central glycerol portion of the molecule.|alt=A space-filling model of an unsaturated triglyceride.]]{{Fats}} [[File:Fat_composition_in_foods.png|thumb|Composition of fats from various foods, as percentage of their total fat.]] In [[nutrition science|nutrition]], [[biology]], and [[chemistry]], '''fat''' usually means any [[ester]] of [[fatty acid]]s, or a mixture of such [[chemical compound|compounds]]; most commonly those that occur in living beings or in [[food]]. The term often refers specifically to [[triglyceride]]s (triple esters of [[glycerol]]), that are the main components of [[vegetable oil]]s and of [[adipose tissue|fatty tissue]] in animals and humans; or, even more narrowly, to triglycerides that are solid or semisolid at room temperature, thus excluding oils. The term may also be used more broadly as a synonym of [[lipid]] -- any substance of biological relevance, composed of [[carbon]], [[hydrogen]], or [[oxygen]], that is insoluble in water but soluble in [[non-polar solvent]]s. In this sense, besides the triglycerides, the term would include several other types of compounds like [[monoglyceride|mono-]] and [[diglyceride]]s, [[phospholipid]]s (such as [[lecithin]]), [[sterol]]s (such as [[cholesterol]]), [[wax]]es (such as [[beeswax]]), and free fatty acids, which are usually present in human diet in smaller amounts. Fats are one of the three main [[macronutrient]] groups in human [[diet (nutrition)|diet]], along with [[carbohydrate]]s and [[protein]]s, and the main components of common food products like [[milk]], [[butter]], [[tallow]], [[lard]], [[bacon]], and [[cooking oil]]s. They are a major and dense source of [[food energy]] for many animals and play important structural and [[metabolism|metabolic]] functions, in most living beings, including energy storage, waterproofing, and [[thermal insulator|thermal insulation]]. The human body can produce the fat that it needs from other food ingredients, except for a few [[essential fatty acid]]s that must be included in the diet. Dietary fats are also the carriers of some [[flavor]] and [[aroma]] ingredients and [[vitamin]]s that are [[lipophilicity|not water-soluble]]. ==Chemical structure== [[File:Unsaturated Triglyceride Structural Formula V1.svg|thumb|Example of a natural triglyceride with three different fatty acids. One fatty acid 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 bond]]s within the carbon chain. All carbon-carbon double bonds shown are ''cis'' isomers. ]] The most important elements in the chemical makeup of fats are the [[fatty acid]]s. The molecule of a fatty acid consists of a [[carboxyl group]] HO(O=)C– connected to an unbranched [[alkyl]] group –{{chem|(CH|''x''|)|''n''}}H: namely, a chain of carbon atoms, joined by single, double, or (more rarely) triple bonds, with all remaining free bonds filled by [[hydrogen]] atoms The most common type of fat, in human diet and most living beings, is a [[triglyceride]], an ester of the triple [[alcohol (chemistry)|alcohol]] [[glycerol]] {{chem|H(–CHOH–)|3|H}} and three fatty acids. The molecule of a trigliceride can be described as resulting from a [[condensation reaction]] (specifically, [[esterification]]) between each of glycerol's –OH groups and the HO– part of the carboxyl group HO(O=)C– of each fatty acid, forming an [[ester group|ester bridge]] –O–(O=)C– with elimination of a water molecule {{chem|H|2|O}}. Other less common types of fats include [[diglycerides]] and [[monoglycerides]], where the esterification is limited to two or just one of glycerol's –OH groups. Other alcohols, such as [[cetyl alcohol]] (predominant in [[spermaceti]]), may replace glycerol. In the [[phospholipid]]s, one of the fatty acids is replaced by [[phosphoric acid]] or a monoester thereof. ===Conformation=== The shape of fat and fatty acid molecules is usually not well-defined. Any two parts of a molecule that are connected by just one single bond are free to rotate about that bond. Thus a fatty acid molecule with ''n'' simple bonds can be deformed in ''n''-1 independent ways (counting also rotation of the terminal [[methyl group]]). Such rotation cannot happen across a double bond, except by breaking and then reforming it with one of the halves of the molecule rotated by 180 degrees, which requires crossing a significant [[energy barrier]]. Thus a fat or fatty acid molecule with double bonds (excluding at the very end of the chain) can have multiple [[cis-trans isomer]]s with significantly different chemical and biological properties. Each double bond reduces the number of conformational [[degree of freedom|degrees of freedom]] by one. Each triple bond forces the four nearest carbons to lie in a straight line, removing two degrees of freedom. It follows that depictions of "saturated" fatty acids with no double bonds (like stearic) having a "straight zig-zag" shape, and those with one ''cis'' bond (like oleic) being bent in an "elbow" shape are somewhat misleading. While the latter are a little less flexible, both can be twisted to assume similar straight or elbow shapes. In fact, outside of some specific contxts like crystals or [[lipid bilayer|bilayer membrane]]s, both are more likely to be found in randomly contorted configurations than in either of those two shapes. ===Examples=== {|class="wikitable" |+Examples of 18-carbon [[fatty acids]]. |- ! [[Stearic acid]]
saturated | [[File:Stearic-acid-3D-balls.png|160px]] |- ! [[Oleic acid]]
unsaturated
''cis''-8 | [[File:Oleic-acid-3D-ball-&-stick.png|160px]] |- ! [[Elaidic acid]]
unsaturated
''trans''-8 | [[File:Elaidic-acid-3D-balls.png|160px]] |- ! [[Vaccenic acid]]
unsaturated
''trans''-11 | [[File:Vaccenic-acid-3D-balls.png|160px]] |- |} Stearic acid is a saturated fatty acid (with only single bonds) found in animal fats, and is the intended product in full hydrogenation. Oleic acid has a double bond (thus being "unsaturated") with ''cis'' geometry about midway in the chain; it makes up 55–80% of olive oil. Elaidic acid is its ''trans'' isomer; it may be present in partially hydrogenated vegetable oils, and also occurs in the fat of the [[durian]] fruit (about 2%) and in milk fat (less than 0.1%). Vaccenic acid is another ''trans'' acid that differs from elaidic only in the position of the double bond; it also occurs in milk fat (about 1-2%). ==Nomenclature== ===Common fat names=== Fats are usually named after their source (like [[butterfat]], [[olive oil]], [[cod liver oil]], [[tail fat]]) or have traditional names of their own (like butter, lard, [[ghee]], and [[margarine]]). Some of these names refer to products that contain substantial amounts of other components besides fats proper. ===Chemical fatty acid names=== In chemistry and biochemistry, [[list of saturated fatty acids|dozens of saturated fatty acids]] and of [[list of unsaturated fatty acids|hundreds of unsaturated ones]] have proper scientfic/technical names usually inspired by their source fats (butyric, [[caprylic acid|caprylic]], stearic, oleic, [[palmitic acid|palmitic]], and [[nervonic acid|nervonic]]), but sometimes their discoverer ([[mead acid|mead]], [[osbond acid|osbond]]). A triglyceride would then be named as an ester of those acids, such as "glyceryl 1,2-dioleate 3-palmitate". ===IUPAC=== In the general chemical nomenclature developed by the [[International Union of Pure and Applied Chemistry]] (IUPAC), the recommended name of a fatty acid, derived from the name of the corresponding [[hydrocarbon]], completely describes its structure, by specifying the number of carbons and the number and position of the double bonds. Thus, for example, oleic acid would be called "(9Z)-octadec-9-enoic acid", meaning that it has a 18 carbon chain ("octadec") with a carboxyl at one end ("oic") and a double bound at carbon 9 counting from the carboxyl ("9-en"), and that the configuration of the single bonds adjacent to that double bond is ''cis'' ("(9Z)") The IUPAC nomenclature can also handle branched chains and derivatives where hydrogen atoms are replaced by other chemical groups. A triglyceride would then be named according to general ester rules as, for example, "propane-1,2,3-tryl 1,2-bis((9Z)-octadec-9-enoate) 3-(hexadecanoate)". ===Fatty acid code=== A notation specific for fatty acids with unbranched chain, that is as precise as the IUPAC one but easier to parse, is a code of the form "{N}:{D} cis-{CCC} trans-{TTT}", where {N} is the number of carbons (including the carboxyl one), {D} is the number of double bonds, {CCC} is a list of the positions of the ''cis'' double bonds, and {TTT} is a list of the postions of the ''trans'' bounds. Either list and the label is omitted if there are no bounds of that type. Thus, for example, the codes for stearic, oleic, elaidic, and vaccenic acids would be "18:0", "18:1 cis-9", "18:1 trans-9", and "18:1 trans-11", respectively. The code for [[alpha-Oleostearic acid|α-oleostearic acid]], which is "(9E,11E,13Z)-octadeca-9,11,13-trienoic acid" in the IUPAC nomenclature, has the code "18:3 trans-9,11 cis-13" ==Classification== {{main|fatty acid}} ===By chain length=== Fats can be classified according to the lengths of the carbon chains of their constituent fatty acids. Most chemical properties, such as melting point and acidity, vary gradually with this parameter, so there is no sharp division. Chemically, [[formic acid]] (1 carbon) and [[acetic acid]] (2 carbons) could be viewed as the shortest fatty acids; then [[triformin]] would be the simplest trigliceride. However, the terms "fatty acid" and "fat" are usually reserved for compounds with substantially longer chains.{{cn|date=August 2020}} A division commonly made in biochemistry and nutrition is:{{cn|date=August 2020}} * '''Short-chain fatty acid''' ('''SCFA''') with less than six carbons (e. g. [[butyric acid]]). * '''Medium-chain fatty acid''' ('''MCFA''') with 6 to 12 carbons (e.g. [[capric acid]]). * '''Long-chain fatty acids''' ('''LCFA''') with 13 to 21 carbons (e.g. [[petroselinic acid]]). * '''Very long chain fatty acids''' ('''VLCFA''') with 22 or more carbons (e. g. [[cerotic acid]] with 26) A triglyceride molecule may have fatty acid elements of different lengths, and a fat product will often be a mix of various triglycerides. 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. ===Saturated and unsaturated fats=== For human nutrition, an important classification of fats is based on the number and position of [[double bond]]s in the constituent fatty acids. '''Saturated fat''' has a predominance of [[saturated fatty acid]]s, without any double bonds, while '''unsaturated fat''' has predominantly [[unsaturated fatty acid|unsaturated acids]] with double bonds. (The names refer to the fact that each double bond means two fewer hydrogen atoms in the chemical formula. Thus, a saturated fatty acid, having no double bonds, has the maximum number of hydrogen atoms for a given number of carbon atoms — that is, it is "saturated" with hydrogen atoms.) Unsaturated fatty acids are further classified into '''[[monounsaturated fatty acid|monounsaturated]]''' (MUFAs), with a single double bond, and '''[[polyunsaturated fatty acid|polyunsaturated]]''' (PUFAs), with two or more. Natural fats usually contain several different saturated and unsaturated acids, even on the same molecule. For example, in most vegetable oils, the saturated [[palmitic acid|palmitic]] (C16:0) and [[stearic acid|stearic]] (C18:0) [[acyl group|acid residues]] are usually attached to positions 1 and 3 (sn1 and sn3) of the glycerol hub, whereas the middle position (sn2) is usually occupied by an unsaturated one, such as [[oleic acid|oleic]] (C18:1, ω–9) or [[linoleic acid|linoleic]] (C18:2, ω–6).) Saturated fats generally have a higher melting point than usaturated ones with the same molecular weight, and thus are more likely to be solid at room temperature. For example, the 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. Unsaturated fats are prone to [[oxidation]] by air, which causes them to become rancid and inedible. The double bonds in unsaturated fats can be converted into single bonds by reaction with hydrogen effected by a catalyst. This process, called [[hydrogenation]], is used to turn vegetable vegetable oils into solid or semisolid [[vegetable fat]]s like [[margarine]], which can substitute for tallow and butter and (unlike unsaturated fats) can be stored indefinitely without becoming rancid. However, partial hydrogenation also creates some unwanted ''trans'' acids from ''cis'' acids.{{cn|date=August 2020}} In cellular [[metabolism]], unsaturated fat molecules yield slightly less less energy (i.e., fewer [[calories]]) than an equivalent amount of saturated fat. The heats of combustion of unsaturated, mono-, di-, and tri-unsaturated 18-carbon fatty acid esters have been measured as 2859, 2828, 2794, and 2750 kcal/mol; or, on a weight basis, 10.75, 10.71, 10.66, and 10.58 kcal/g — a decrease of about 0.6% for each additional double bond. The greater the degree of unsaturation in a fatty acid (i.e., the more double bonds in the fatty acid) the more vulnerable it is to [[lipid peroxidation]] ([[rancidification|rancidity]]). [[Antioxidant]]s can protect unsaturated fat from lipid peroxidation. ===Cis and trans fats=== Another important classification of unsaturated fatty acids considers the [[cis-trans isomerism|''cis''-''trans'' isomerism]], the spatial arrangement of the C–C [[single bond]]s adjacent to the double bonds. Most unsaturated fatty acids that occur in nature have those bonds in the ''cis'' ("same side") configuration. Partial [[hydrogenation]] of ''cis'' fats can turn some of their fatty acids into ''trans'' ("opposite sides") variety. ===Omega number=== Another classification considers the position of the double bonds relative to the ''end'' of the chain (opposite to the [[carboxyl group]]). The position is denoted by "ω−''k''" or "n−''k''", meaning that there is a double bond between carbons ''k'' and ''k''+1 counted from 1 at that end. For example, [[alpha-Linolenic acid]] is a "ω−3" or "n−3" acid, meaning that there is a double bond between the third and fourth carbons, counted from that end; that is, its [[condensed structural formula|structural formula]] ends with –CH=CH–{{chem|CH|2}}–{{chem|CH|3}}. The explanation for this notation is that the carbons of a fatty acid with n carbons are usually numbered 1 to n, starting with the one in the [[carboxyl group]]; or with [[Greek alphabet|Greek letters]] α (''alpha''), β (''beta''), and so on, starting with carbon 2. Thus, by an abuse of these conventions, the last carbon of the chain came to be indicated "n" or "ω" (''omega''), the last letter of the Greek alphabet. The notations "n−3" and "ω−3" were meant to be read as "n minus three" or "omega minus three", the dash being a minus sign; meaning that, in a chain with 18 carbons, the double bond is between carbons 18-3=15 and 16. However, in non-scientific literature the second notation is commonly written "ω-3" or "omega-3" (with a hyphen) and read "omega-three". ====Examples of saturated fatty acids==== {{Main|List of saturated fatty acids}} Some common examples of fatty acids: * [[Butyric acid]] with 4 carbon atoms (contained in [[butter]]) * [[Lauric acid]] with 12 carbon atoms (contained in [[coconut oil]], [[palm kernel oil]], and [[breast milk]]) * [[Myristic acid]] with 14 carbon atoms (contained in cow's [[milk]] and dairy products) * [[Palmitic acid]] with 16 carbon atoms (contained in [[palm oil]] and [[meat]]) * [[Stearic acid]] with 18 carbon atoms (also contained in [[meat]] and [[cocoa butter]]) ====Examples of unsaturated fatty acids==== {{Main|List of unsaturated fatty acids}} * [[Myristoleic acid]] C14:1, ω−5, ''cis''-9-tetradecenoic acid * [[Sapienic acid]] C16:1 ω−10, ''cis''-6-Hexadecenoic acid * [[Palmitoleic acid]] C16:1, ω−7 , ''cis''-9-hexadecenoic acid * [[Oleic acid]] C18:1 ω−9, ''cis''-9-octadecenoic acid * [[Petroselinic acid]] C18:1 ω−12, ''cis''-Octadec-6-enoic acid * [[cis-Vaccenic acid|''cis''-Vaccenic acid]], C18:1 ω−7), ''cis''-11-octadecenoic acid * [[Vaccenic acid]] C18:1 ω−7, ''trans''-11-octadecenoic acid * [[Elaidic acid]] 18:1 ω−9, ''trans''-9-octadecenoic acid (''trans''-oleic acid) * [[Linoleic acid]] * [[Linolenic acid]] * [[Paullinic acid]] C20:1 ω−7, ''cis''-13-eicosenoic acid * [[Gadoleic acid]] C20:1 ω−11, ''cis''-9-icosenoic acid * [[11-Eicosenoic acid|Gondoic acid]] 20:1 ω−9, ''cis''-11-eicosenoic acid * [[Erucic acid]] C22:1 ω−9, ''cis''-15-tetracosenoic acid * [[Brassidic acid]] C22:1 ω−9, ''trans''-15-tetracosenoic acid * [[Nervonic acid]] C24:1 ω−9, | ''cis''-15-tetracosenoic acid * [[Arachidonic acid]] == Biological importance == In humans and many animals, fats serve both as energy sources and as stores for energy in excess of what the body needs immediately. Each gram of fat when burned or metabolized releases about 9 [[Calorie|food calories]] (37 [[Joule|kJ]] = 8.8 [[Calorie|kcal]]). Fats are also sources of [[essential fatty acid]]s, an important dietary requirement. [[Vitamin]]s [[Vitamin A|A]], [[Vitamin D|D]], [[Vitamin E|E]], and [[Vitamin K|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 against 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.{{cn|date=August 2020}} This helps to protect vital organs, until such time as the offending substances can be metabolized or removed from the body by such means as [[excretion]], [[urination]], accidental or intentional [[bloodletting]], [[sebum]] excretion, and [[hair]] growth. ===Adipose tissue=== [[File:Fatmouse.jpg|right|thumb|The [[obesity|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.]] In animals, [[adipose tissue]], or fatty tissue is the body's means of storing metabolic energy over extended periods of time. [[Adipocyte]]s (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 [[circulatory system|circulation]]. These metabolic activities are regulated by several hormones (e.g., [[insulin]], [[glucagon]] and [[epinephrine]]). Adipose tissue also secretes the hormone [[leptin]]. 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., [[hormone]]s), 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.{{cn|date=August 2020}} ==Production and processing== A variety of chemical and physical techniques are used for the production and processing of fats, both industrially and in cottage or home settings. They include: * [[Oil pressing|Pressing]] to extract liquid fats from fruits, seeds, or [[alga]]e, e.g. [[olive oil]] from [[olive]]s; * [[Solvent extraction]] using solvents like [[hexane]] or [[supercritical carbon dioxide]]. * [[Rendering (animal products)|Rendering]], the melting of fat in adipose tissue, e.g. to produce tallow, lard, [[fish oil]], and [[whale oil]]. * [[Churning]] of milk to produce butter. * [[Hydrogenation]] to reduce the degree of unsaturation of the fatty acids. * [[Fat interesterification|Interesterification]], the rearrangement of fatty acids across different triglicerides. * [[Winterization (of oil)|Winterization]] to remove oil components with higher melting points. * [[Clarified butter|Clarification]] of butter. ==Composition of dietary fats== Different foods contain different amounts of fat with different proportions of saturated and unsaturated fatty acids. Most animal fats, such as [[lard]], [[schmaltz]] and [[sausage]]s, fatty meats and [[dairy products]] made with whole or reduced fat milk like [[yogurt]], [[ice cream]], [[cheese]] and [[butter]] have mostly saturated fatty acids (and some have significant contents of [[dietary cholesterol]]). Industrialized [[baked goods]] may use fats with high unsaturated fat contents as well, especially those containing partially [[hydrogenation|partially hydrogenated oil]]s, and [[processed foods]] that are [[deep-fried]] in [[vegetable_oil#Hydrogenated_oils|hydrogenated oil]] are high in saturated fat content.. Plants and fish oil generally contain a higher proportion of unsaturated acids, although there are exceptions such as [[coconut oil]] and [[palm kernel oil]]. Foods containing unsaturated fats include [[avocado]], [[nut (fruit)|nuts]], [[olive oil]]s, and [[vegetable oil]]s such as [[canola]]. The most common fatty acids in human diet are unsaturated or mono-unsaturated. Polyunsaturated acids can be found mostly in nuts, seeds, fish, seed oils, and [[oyster]]s. While it is the ''nutritional'' aspects of polyunsaturated fatty acids that are generally of greatest interest, these materials also have non-food applications. They include the [[drying oils]], such as [[linseed oil|linseed (flax seed)]], [[tung oil|tung]], [[poppyseed oil|poppy seed]], [[perilla oil|perilla]], and [[walnut oil]], which [[polymerize]] on exposure to [[oxygen]] to form solid films, and are used to make [[paints]] and [[varnishes]]. ===Saturated=== {|class="wikitable sortable" |+Saturated esterified fatty acids as percentage of total fat ! width="120pt"| Food !! width="70pt"| [[Lauric acid]] !! width="70pt"| [[Myristic acid]] !! width="70pt"| [[Palmitic acid]] !! width="70pt"| [[Stearic acid]] |- | [[Coconut oil]] || 47% || 18% || 9% || 3% |- | [[Palm kernel oil]] || 48% || 1% || 44% || 5% |- | [[Butter]] || 3% || 11% || 29% || 13% |- | [[Ground beef]] || 0% || 4% || 26% || 15% |- | [[Salmon]] || 0% || 1% || 29% || 3% |- | [[Egg (food)|Egg]] yolks || 0% || 0.3% || 27% || 10% |- | [[Cashew]]s || 2% || 1% || 10% || 7% |- | [[Soybean oil]] || 0% || 0% || 11% || 4% |} ===Monounsaturated=== Monounsaturated fats are found in animal flesh such as red [[meat]], whole milk products, [[Nut (fruit)|nuts]], and high fat fruits such as olives and [[avocado]]s. [[Algal oil]] is about 92% monounsaturated fat. [[Olive oil]] is about 75% monounsaturated fat. The high oleic variety [[sunflower oil]] contains at least 70% monounsaturated fat. [[Canola oil]] and [[cashew]]s are both about 58% monounsaturated fat.{{Citation needed|date=August 2015}} [[Tallow]] (beef fat) is about 50% monounsaturated fat. and [[lard]] is about 40% monounsaturated fat.{{Citation needed|date=August 2015}} Other sources include [[hazelnut]], [[avocado oil]], [[macadamia nut oil]], [[Grape seed oil|grapeseed oil]], groundnut oil ([[peanut oil]]), [[sesame oil]], [[corn oil]], [[popcorn]], [[whole grain]] [[wheat]], [[cereal]], [[oatmeal]], [[almond oil]], [[sunflower oil]], [[hemp oil]], and [[tea-oil Camellia]]. ===Polyunsaturated=== Food sources of polyunsaturated fats include: {| class="wikitable sortable" |- ! Food source (100g) !! Polyunsaturated fat (g) |- | [[Walnuts]] || 47 |- | [[Canola Oil]] || 34 |- | [[Sunflower seed]]s || 33 |- | [[Sesame Seed]]s || 26 |- | [[Salvia hispanica|Chia Seeds]] || 23.7 |- | [[Peanut#Dry roasted peanuts|Unsalted Peanuts]] || 16 |- | [[Peanut Butter]] || 14.2 |- | [[Avocado oil|Avocado Oil]] || 13.5 |- | [[Olive Oil]] || 11 |- |[[Safflower oil|Safflower Oil]] |12.82 |- | [[Seaweed]] || 11 |- | [[Sardines]] || 5 |- | [[Soybeans]] || 7 |- | [[Tuna]] || 14 |- | [[Salmon as food|Wild Salmon]] || 17.3 |- | [[Whole Grain]] [[Wheat]] || 9.7 |} ===Trans=== In nature, unsaturated fatty acids generally have [[cis–trans isomerism|''cis'' as opposed to ''trans'']] configurations. Nevertheless, ''trans'' fatty acids occur in small amounts in meat and milk fat. {| class="wikitable" |+ Trans fat contents in various foods, ranked in g per 100 g |- ! Food type ! Trans fat content |- | shortenings | 10g to 33 g |- | butter |2g to 7 g |- | whole milk |0.07g to 0.1 g |- | animal fat | 0g to 5 g |- |ground beef |1 g |} A type of trans fat occurs naturally in the milk and body fat of [[ruminant]]s (such as cattle and sheep) at a level of 2–5% of total fat. Natural ''trans'' fats, which include [[conjugated linoleic acid]] (CLA) and [[vaccenic acid]], originate in the [[rumen]] of these animals. CLA has two double bonds, one in the ''cis'' configuration and one in ''trans'', which makes it simultaneously a ''cis''- and a ''trans''-fatty acid.{{}} ==Saturated fat== Guidelines released by many medical organizations, including the [[World Health Organization]], have advocated for reduction in the intake of saturated fat to promote health and reduce the risk from cardiovascular diseases. Many review articles also recommend a diet low in saturated fat and argue it will lower risks of [[cardiovascular disease]]s, [[diabetes]], or death. A small number of contemporary reviews have challenged these conclusions, though predominant medical opinion is that saturated fat and cardiovascular disease are closely related. ===Association with diseases=== ====Cardiovascular disease==== {{Main|Saturated fat and cardiovascular disease}} The effect of saturated fat on heart disease has been extensively studied. There are strong, consistent, and graded relationships between saturated fat intake, [[blood cholesterol]] levels, and the epidemic of cardiovascular disease. The relationships are accepted as causal. Many health authorities such as the [[Academy of Nutrition and Dietetics]], the [[British Dietetic Association]], [[American Heart Association]], the [[World Heart Federation]], the British [[National Health Service]], among others, advise that saturated fat is a [[risk factor]] for cardiovascular disease. The World Health Organization in May 2015 recommends switching from saturated to unsaturated fats. There is moderate quality evidence that reducing the proportion of saturated fat in the diet, and replacing it with unsaturated fats or carbohydrates over a period of at least two years, leads to a reduction in the risk of cardiovascular disease. =====Dyslipidemia===== {{See also|Lipid hypothesis}} The consumption of saturated fat is generally considered a risk factor for [[dyslipidemia]], which in turn is a risk factor for some types of [[cardiovascular disease]]. Abnormal blood lipid levels, that is high total cholesterol, high levels of triglycerides, high levels of [[low-density lipoprotein]] (LDL, "bad" cholesterol) or low levels of [[high-density lipoprotein]] (HDL, "good" cholesterol) cholesterol are all associated with increased risk of heart disease and stroke. Meta-analyses have found a significant relationship between saturated fat and serum cholesterol levels. High total cholesterol levels, which may be caused by many factors, are associated with an increased risk of cardiovascular disease.{{cite journal |vauthors=Bucher HC, Griffith LE, Guyatt GH | title = Systematic review on the risk and benefit of different cholesterol-lowering interventions | journal = Arteriosclerosis, Thrombosis, and Vascular Biology | volume = 19 | issue = 2 | pages = 187–195 | date = February 1999 | pmid = 9974397 | doi = 10.1161/01.atv.19.2.187 | doi-access = free }} However, other indicators measuring cholesterol such as high total/HDL cholesterol ratio are more predictive than total [[serum cholesterol]]. In a study of [[myocardial infarction]] in 52 countries, the [[apolipoprotein B|ApoB]]/[[apolipoprotein A1|ApoA1]] (related to LDL and HDL, respectively) ratio was the strongest predictor of CVD among all risk factors. There are other pathways involving [[obesity]], [[triglyceride]] levels, [[insulin resistance|insulin sensitivity]], [[endothelium|endothelial function]], and [[thrombogenicity]], among others, that play a role in CVD, although it seems, in the absence of an adverse blood lipid profile, the other known risk factors have only a weak [[atherogenic]] effect. Different saturated fatty acids have differing effects on various lipid levels. ====Cancer==== =====Breast cancer===== {{Main|Epidemiology and etiology of breast cancer#Specific dietary fatty acids}} A meta-analysis published in 2003 found a significant positive relationship in both control and cohort studies between saturated fat and breast cancer. However two subsequent reviews have found weak or insignificant associations of saturated fat intake and breast cancer risk, and note the prevalence of confounding factors. =====Colorectal cancer===== One review found limited evidence for a positive relationship between consuming animal fat and incidence of colorectal cancer. =====Ovarian cancer===== Meta-analyses of clinical studies found evidence for increased risk of ovarian cancer by high consumption of saturated fat. =====Prostate cancer===== {{Further|Prostate cancer#Oils and fatty acids}} Some researchers have indicated that serum [[myristic acid]] and [[palmitic acid]] and dietary myristic and palmitic saturated fatty acids and serum palmitic combined with [[Tocopherol#Alpha-tocopherol|alpha-tocopherol]] supplementation are associated with increased risk of prostate cancer in a dose-dependent manner. These associations may, however, reflect differences in intake or metabolism of these fatty acids between the precancer cases and controls, rather than being an actual cause. ====Bones==== Mounting evidence indicates that the amount and type of fat in the diet can have important effects on bone health. Most of this evidence is derived from animal studies. The data from one study indicated that bone mineral density is negatively associated with saturated fat intake, and that men may be particularly vulnerable. ===Dietary recommendations=== Recommendations to reduce or limit dietary intake of saturated fats are made by the World Health Organization, American Heart Association, Health Canada, the US Department of Health and Human Services, the UK National Health Service, the Australian Department of Health and Aging, the Singapore Ministry of Health, the Indian Ministry of Health and Family Wellfare, the New Zealand Ministry of Health, and Hong Kong's Department of Health. In 2003, the World Health Organization (WHO) and Food and Agriculture Organization (FAO) expert consultation report concluded that "intake of saturated fatty acids is directly related to cardiovascular risk. The traditional target is to restrict the intake of saturated fatty acids to less than 10% of daily energy intake and less than 7% for high-risk groups. If populations are consuming less than 10%, they should not increase that level of intake. Within these limits, intake of foods rich in myristic and palmitic acids should be replaced by fats with a lower content of these particular fatty acids. In developing countries, however, where energy intake for some population groups may be inadequate, energy expenditure is high and body fat stores are low (BMI <18.5 kg/m2). The amount and quality of fat supply has to be considered keeping in mind the need to meet energy requirements. Specific sources of saturated fat, such as coconut and palm oil, provide low-cost energy and may be an important source of energy for the poor." A 2004 statement released by the [[Centers for Disease Control]] (CDC) determined that "Americans need to continue working to reduce saturated fat intake…" In addition, reviews by the [[American Heart Association]] led the Association to recommend reducing saturated fat intake to less than 7% of total calories according to its 2006 recommendations. This concurs with similar conclusions made by the US [[Department of Health and Human Services]], which determined that reduction in saturated fat consumption would positively affect health and reduce the prevalence of heart disease. The [[United Kingdom]], [[National Health Service]] claims the majority of British people eat too much saturated fat. The [[British Heart Foundation]] also advises people to cut down on saturated fat. People are advised to cut down on saturated fat and read labels on food they buy. A 2004 review stated that "no lower safe limit of specific saturated fatty acid intakes has been identified" and recommended that the influence of varying saturated fatty acid intakes against a background of different individual lifestyles and genetic backgrounds should be the focus in future studies. Blanket recommendations to lower saturated fat were criticized at a 2010 conference debate of the [[American Dietetic Association]] for focusing too narrowly on reducing saturated fats rather than emphasizing increased consumption of healthy fats and unrefined carbohydrates. Concern was expressed over the health risks of replacing saturated fats in the diet with refined carbohydrates, which carry a high risk of obesity and heart disease, particularly at the expense of [[polyunsaturated fat]]s which may have health benefits. None of the panelists recommended heavy consumption of saturated fats, emphasizing instead the importance of overall dietary quality to cardiovascular health. In a 2017 comprehensive review of the literature and clinical trials, the American Heart Association published a recommendation that saturated fat intake be reduced or replaced by products containing monounsaturated and polyunsaturated fats, a dietary adjustment that could reduce the risk of cardiovascular diseases by 30%. ==Unsaturated fat== [[File:Fatchart.svg|thumb|right|Amounts of fat types in selected foods]] Although both monounsaturated and [[polyunsaturated fat]]s can replace saturated fat in the diet, trans unsaturated fats should not. Replacing saturated fats with unsaturated fats helps lower levels of total [[cholesterol]] and [[low-density lipoprotein|LDL]] cholesterol in the [[blood]]. Trans unsaturated fats are an exception because the double bond [[stereochemistry]] predisposes the carbon chains to assume a linear [[Conformational isomerism|conformation]], which conforms to rigid packing as in [[atheroma|plaque]] formation. The geometry of the cis double bond induces a bend in the [[molecule]], thereby precluding rigid formations.{{Citation needed|date=April 2017}}. Although polyunsaturated fats are protective against [[cardiac arrhythmia]]s, a study of post-[[menopause]]al women with a relatively low fat intake showed that polyunsaturated fat is positively associated with progression of [[coronary]] [[atherosclerosis]], whereas [[monounsaturated fat]] is not. This probably is an indication of the greater vulnerability of polyunsaturated fats to [[lipid peroxidation]], against which [[vitamin E|vitamin E]] has been shown to be protective. Although unsaturated fats are conventionally regarded as 'healthier' than saturated fats, the United States [[Food and Drug Administration]] (FDA) recommendation stated that the amount of unsaturated fat consumed should not exceed 30% of one's daily caloric intake.{{citation needed|date=March 2017}} Most foods contain both unsaturated and saturated fats. Marketers advertise only one or the other, depending on which one makes up the majority. Thus, various unsaturated fat vegetable oils, such as olive oils, also contain saturated fat. === Role of dietary fats in insulin resistance === {{refimprove section|date=January 2015}} Incidence of [[insulin resistance]] is lowered with diets higher in monounsaturated fats (especially oleic acid), while the opposite is true for diets high in polyunsaturated fats (especially large amounts of [[arachidonic acid]]) as well as saturated fats (such as [[arachidic acid]]). These ratios can be indexed in the [[phospholipid]]s of human [[skeletal muscle]] and in other tissues as well. This relationship between dietary fats and insulin resistance is presumed secondary to the relationship between insulin resistance and [[inflammation]], which is partially modulated by dietary fat ratios ([[Omega-3 fatty acids|Omega-3]]/[[Omega-6 fatty acids|6]]/[[Omega-9 fatty acids|9]]) with both omega 3 and 9 thought to be anti-inflammatory, and omega 6 pro-inflammatory (as well as by numerous other dietary components, particularly [[Health effects of polyphenols|polyphenols]] and exercise, with both of these anti-inflammatory). Although both pro- and anti-inflammatory types of fat are [[biology|biologically]] necessary, fat dietary ratios in most US diets are skewed towards Omega 6, with subsequent disinhibition of inflammation and potentiation of insulin resistance. But this is contrary to the suggestion of [[Monounsatura line 350: ** ref not closed [{{cite journal | vauthors = Lovejoy JC | title = The influence of dietary fat on insulin resistance | journal = Current Diabetes Reports | volume = 2 | issue = 5 | pages = 435–40 | date = October 2002 | pmid = 12643169 | doi = 10.1007/s11892-002-0098-y }}] line 351: ** ref not closed [{{cite journal | vauthors = Fukuchi S, Hamaguchi K, Seike M, Himeno K, Sakata T, Yoshimatsu H | title = Role of fatty acid composition in the development of metabolic disorders in sucrose-induced obese rats | journal = Experimental Biology and Medicine | volume = 229 | issue = 6 | pages = 486–93 | date = June 2004 | pmid = 15169967 | doi = 10.1177/153537020422900606 }}] line 355: ** ref not closed [{{cite web | title = You Can Control Your Cholesterol: A Guide to Low-Cholesterol Living | publisher = [[Merck & Co. | MerckSource]] | url = http://www.mercksource.com/pp/us/cns/cns_krames_template.jspzQzpgzEzzSzppdocszSzuszSzcnszSzcontentzSzkrameszSz1292_01zPzhtm | access-date = 2018-01-02 | archive-url = https://web.archive.org/web/20090303124418/http://www.mercksource.com/pp/us/cns/cns_krames_template.jspzQzpgzEzzSzppdocszSzuszSzcnszSzcontentzSzkrameszSz1292_12zPzhtm | archive-date = 2009-03-03 | url-status= dead }}] ted fat#Relation to health|more recent studies]], in which polyunsaturated fats are shown as protective against insulin resistance. === Membrane composition as a metabolic pacemaker === Studies on the [[cell membrane]]s of [[mammal]]s and [[reptile]]s discovered that mammalian cell membranes are composed of a higher proportion of polyunsaturated fatty acids ([[Docosahexaenoic acid|DHA]], [[omega-3 fatty acid]]) than [[reptile]]s. Studies on bird fatty acid composition have noted similar proportions to mammals but with 1/3rd less omega-3 fatty acids as compared to [[omega-6 fatty acid|omega-6]] for a given body size. This fatty acid composition results in a more fluid cell membrane but also one that is permeable to various ions (H+ & Na+), resulting in cell membranes that are more costly to maintain. This maintenance cost has been argued to be one of the key causes for the high metabolic rates and concomitant [[warm-blooded]]ness of mammals and birds. However polyunsaturation of cell membranes may also occur in response to chronic cold temperatures as well. In [[fish]] increasingly cold environments lead to increasingly high cell membrane content of both monounsaturated and polyunsaturated fatty acids, to maintain greater membrane fluidity (and functionality) at the lower [[temperature]]s. ===Omega-three fatty acids=== {{main|Omega-3 fatty acid}} The [[Omega-3 fatty acid|ω−3 fatty acids]] have received substantial atterntion in recent years. ===Monounsaturated fat=== ====Health==== The large scale KANWU study found that increasing monounsaturated fat and decreasing saturated fat intake could improve insulin sensitivity, but only when the overall fat intake of the diet was low.{{cite journal | vauthors = Vessby B, Uusitupa M, Hermansen K, Riccardi G, Rivellese AA, Tapsell LC, Nälsén C, Berglund L, Louheranta A, Rasmussen BM, Calvert GD, Maffetone A, Pedersen E, Gustafsson IB, Storlien LH | title = Substituting dietary saturated for monounsaturated fat impairs insulin sensitivity in healthy men and women: The KANWU Study | journal = Diabetologia | volume = 44 | issue = 3 | pages = 312–9 | date = March 2001 | pmid = 11317662 | doi = 10.1007/s001250051620 | doi-access = free }} However, some monounsaturated fatty acids (in the same way as saturated fats) may promote [[insulin resistance]], whereas polyunsaturated fatty acids may be protective against insulin resistance.{{cite journal | vauthors = Lovejoy JC | title = The influence of dietary fat on insulin resistance | journal = Current Diabetes Reports | volume = 2 | issue = 5 | pages = 435–40 | date = October 2002 | pmid = 12643169 | doi = 10.1007/s11892-002-0098-y }} {{cite journal | vauthors = Fukuchi S, Hamaguchi K, Seike M, Himeno K, Sakata T, Yoshimatsu H | title = Role of fatty acid composition in the development of metabolic disorders in sucrose-induced obese rats | journal = Experimental Biology and Medicine | volume = 229 | issue = 6 | pages = 486–93 | date = June 2004 | pmid = 15169967 | doi = 10.1177/153537020422900606 }} Studies have shown that substituting dietary monounsaturated fat for saturated fat is associated with increased daily physical activity and resting energy expenditure. More physical activity was associated with a higher-oleic acid diet than one of a [[palmitic acid]] diet. From the study, it is shown that more monounsaturated fats lead to less anger and irritability. Foods containing monounsaturated fats reduce [[low-density lipoprotein]] (LDL) cholesterol,{{cite web | title = You Can Control Your Cholesterol: A Guide to Low-Cholesterol Living | publisher = [[Merck & Co. | MerckSource]] | url = http://www.mercksource.com/pp/us/cns/cns_krames_template.jspzQzpgzEzzSzppdocszSzuszSzcnszSzcontentzSzkrameszSz1292_01zPzhtm | access-date = 2018-01-02 | archive-urline 356: ** ref not closed [{{cite web | title = Monounsaturated Fat | publisher = American Heart Association | url = https://healthyforgood.heart.org/Eat-smart/Articles/Monounsaturated-Fats | access-date = 2018-04-19 | archive-url = https://web.archive.org/web/20180307184535/https://healthyforgood.heart.org/Eat-smart/Articles/Monounsaturated-Fats | archive-date = 2018-03-07 | url-status = live] l = https://web.archive.org/web/20090303124418/http://www.mercksource.com/pp/us/cns/cns_krames_template.jspzQzpgzEzzSzppdocszSzuszSzcnszSzcontentzSzkrameszSz1292_12zPzhtm | archive-date = 2009-03-03 | url-status= dead }} while possibly increasing [[high-density lipoprotein]] (HDL) cholesterol.{{cite web | title = Monounsaturated Fat | publisher = American Heart Association | url = https://healthyforgood.heart.org/Eat-smart/Articles/Monounsaturated-Fats | access-date = 2018-04-19 | archive-url = https://web.archive.org/web/20180307184535/https://healthyforgood.heart.org/Eat-smart/Articles/Monounsaturated-Fats | archive-date = 2018-03-07 | url-status = live }} Levels of [[oleic acid]] along with other monounsaturated fatty acids in red blood cell membranes were positively associated with [[breast cancer]] risk. The [[saturation index]] (SI) of the same membranes was inversely associated with breast cancer risk. Monounsaturated fats and low SI in erythrocyte membranes are predictors of postmenopausal breast cancer. Both of these variables depend on the activity of the enzyme [[delta-9 desaturase]] (Δ9-d). In children, consumption of monounsaturated oils is associated with healthier serum lipid profiles. The [[Mediterranean diet]] is one heavily influenced by monounsaturated fats. People in Mediterranean countries consume more total fat than Northern European countries, but most of the fat is in the form of monounsaturated fatty acids from olive oil and omega-3 fatty acids from fish, vegetables, and certain meats like lamb, while consumption of saturated fat is minimal in comparison. A 2017 review found evidence that the practice of a Mediterranean diet could lead to a decreased risk of [[cardiovascular diseases]], overall [[cancer]] incidence, [[neurodegenerative diseases]], [[diabetes]], and [[mortality rate | early death]]. A 2018 review showed that the practice of the Mediterranean diet may improve overall health status, such as reduced risk of non-communicable diseases. It also may reduce the social and economic costs of diet-related illnesses. ===Polyunsaturated fat=== ====Health==== ===== Potential benefits ===== Because of their effects in the diet, unsaturated fats (monounsaturated and polyunsaturated) are often referred to as ''good fats''; while saturated fats are sometimes referred to as ''bad fats''. Some fat is needed in the diet, but it is usually considered that fats should not be consumed excessively, unsaturated fats should be preferred, and saturated fats in particular should be limited. In preliminary research, [[omega-3 fatty acid]]s in algal oil, fish oil, fish and seafood have been shown to lower the risk of [[Myocardial infarction | heart attacks]]. Other preliminary research indicates that [[omega-6 fatty acids]] in [[sunflower oil]] and [[safflower oil]] may also reduce the risk of cardiovascular disease. Among omega-3 fatty acids, neither long-chain nor short-chain forms were consistently associated with breast cancer risk. High levels of [[docosahexaenoic acid]] (DHA), however, the most abundant omega-3 [[polyunsaturated fatty acid]] in erythrocyte ([[red blood cell]]) membranes, were associated with a reduced risk of breast cancer. The [[Docosahexaenoic acid | DHA]] obtained through the consumption of polyunsaturated fatty acids is positively associated with cognitive and behavioral performance. In addition [[Docosahexaenoic acid | DHA]] is vital for the [[Grey matter | grey matter structure of the human brain]], as well as retinal stimulation and [[neurotransmission]]. Contrary to conventional advice, an evaluation of evidence from 1966-1973 pertaining to the health impacts of replacing dietary [[saturated fat]] with [[linoleic acid]] found that participants in the group doing so had ''increased'' rates of death from all causes, coronary heart disease, and cardiovascular disease. Although this evaluation was disputed by many scientists, it fueled debate over worldwide dietary advice to substitute polyunsaturated fats for saturated fats. ===== Pregnancy ===== Polyunsaturated fat supplementation does not decrease the incidence of pregnancy-related disorders, such as [[hypertension]] or [[preeclampsia]], but may increase the length of [[gestation]] slightly and decreased the incidence of early premature births. Expert panels in the United States and Europe recommend that pregnant and lactating women consume higher amounts of polyunsaturated fats than the general population to enhance the DHA status of the fetus and newborn. ===== Cancer ===== Results from [[observational study | observational clinical trials]] on polyunsaturated fat intake and cancer have been inconsistent and vary by numerous factors of cancer incidence, including gender and genetic risk. Some studies have shown associations between higher intakes and/or blood levels of polyunsaturated fat omega-3s and a decreased risk of certain cancers, including [[breast cancer | breast]] and [[colorectal cancer]], while other studies found no associations with cancer risk. ==Trans fat== [[File:Margaryn 022.jpg | thumb | upright=1.3 | [[Margarine]], a common product that can contain trans fatty acids]] {{Fats}} Concerns about ''trans'' faty acids in human diet were raised when they appeared as an unintentional byproduct in the industrial processing of vegetable and fish oils in the early 20th century for use in [[margarine]] and later also in snack food, packaged baked goods, and for frying fast food. An analysis of some industrialized foods in 2006 found up to 10% trans fats in breads and cake products, 8% in cookies and crackers, 4% in salty snacks, 7% in cake frostings and sweets, and 26% in margarine and other processed spreads. Another 2010 analysis however found only 0.2% of trans fats margarine and other processed spreads. In food production, liquid cis-unsaturated fats such as vegetable oils are [[Hydrogenation | hydrogenated]] to produce saturated fats, which have more desirable physical properties: e.g., they melt at a desirable temperature (30–40 °C; 86–104 °F); and extend the shelf-life of food. Partial hydrogenation of the unsaturated fat converts some of the cis double bonds into trans double bonds by an [[isomerization reaction]] with the [[catalyst]] used for the hydrogenation, which yields a trans fat. Although trans fats are edible, consuming trans fats has been shown to increase the risk of [[coronary artery disease]] in part by raising levels of [[low-density lipoprotein]] (LDL, often termed "bad cholesterol"), lowering levels of [[high-density lipoprotein]] (HDL, often termed "good cholesterol"), increasing triglycerides in the bloodstream and promoting systemic inflammation. Trans fats also occur naturally, e.g., the [[vaccenic acid]] in breast milk, and some [[isomers]] of [[conjugated linoleic acid]] (CLA). These trans fats occur naturally in meat and dairy products from [[ruminant]]s. Butter, for example, contains about 3% trans fat. Two Canadian studies have shown that vaccenic acid could be beneficial compared to hydrogenated vegetable [[shortening]], or a mixture of pork lard and soy fat, by lowering total LDL and triglyceride levels. A study by the US Department of Agriculture showed that vaccenic acid raises both HDL and LDL cholesterol, whereas industrial trans fats only raise LDL with no beneficial effect on HDL. In light of recognized evidence and scientific agreement, nutritional authorities consider all trans fats equally harmful for health and recommend that their consumption be reduced to trace amounts. The [[World Health Organization]] recommended that trans fats make up no more than 0.9% of a person's diet in 2003 and, in 2018, introduced a 6-step guide to eliminate industrially-produced trans-fatty acids from the global food supply. In many countries, there are legal limits to trans fat content. Trans fats levels can be reduced or eliminated by switching to saturated fats such as [[lard]], [[palm oil]], or fully hydrogenated fats, or by using [[interesterified fat]]. Other alternative formulations can also allow unsaturated fats to be used to replace saturated or partially hydrogenated fats. Hydrogenated oil is not a synonym for trans fat: complete hydrogenation removes all unsaturated fats. ===History=== [[File:Crisco Cookbook 1912.jpg | thumb | Cover of original Crisco cookbook, 1912]] [[Nobel prize | Nobel]] [[laureate]] [[Paul Sabatier (chemist) | Paul Sabatier]] worked in the late 1890s to develop the chemistry of hydrogenation, which enabled the [[margarine]], oil hydrogenation, and synthetic [[methanol]] industries. Whereas Sabatier considered hydrogenation of only 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 | 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 United States rights to the Normann patent;{{cite web | last1=Shurtleff | first1=William | last2=Aoyagi | first2=Akiko | name-list-format = vanc | title=History of Soybeans and Soyfoods: 1100 B.C. to the 1980s | archive-url=https://web.archive.org/web/20051018105337/http://www.thesoydailyclub.com/SFC/MSPproducts501.asp | url=http://www.thesoydailyclub.com/SFC/MSPproducts501.asp | archive-date=18 October 2005}} 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. Before 1910, dietary fats in industrialized nations consisted mostly of [[butterfat]], beef [[tallow]], and [[lard]]. During Napoleon's reign in France in the early 19th century, a type of margarine was invented to feed the troops using tallow and buttermilk. It was not accepted in the United States. In the early 20th century, soybeans began to be imported into the United States 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 allowed margarine, unlike butter, to be taken out of a refrigerator and immediately spread on bread. By some minor changes to the chemical composition of hydrogenated fat, such hydrogenated fat was found to provide superior baking properties compared to lard. Margarine made from hydrogenated soybean oil began to replace butterfat. Hydrogenated fat such as Crisco and [[Spry Vegetable Shortening | Spry]], sold in England, began to replace butter and lard in baking bread, pies, cookies, and cakes in 1920. Production of hydrogenated fats increased steadily until the 1960s, as processed vegetable fats replaced animal fats in the United States and other Western countries. At first, the argument was a financial one due to lower costs; advocates also said that the unsaturated trans fats of margarine were healthier than the [[saturated fat]]s of butter. A [[University of Guelph]] research group has found a way to mix oils (such as olive, soybean, and canola), water, [[monoglyceride]]s, and fatty acids to form a "cooking fat" that acts the same way as trans and saturated fats. ===Hydrogenation=== [[File:Wilhelm Normann.jpg | thumb | [[Wilhelm Normann]] patented the hydrogenation of liquid oils in 1902]] [[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. Typical commercial hydrogenation is partial to obtain a [[malleable]] mixture of fats that is solid at [[room temperature]], but melts during 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-trans isomerism | cis]]'' configuration – from the Latin, meaning "on the same side"). 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 ''[[Cis-trans isomerism | trans]]'', from the Latin, meaning "across". The trans configuration is the lower energy form, and is favored when catalytically equilibrated as a side reaction in hydrogenation. The ''trans'' fatty acid elaidic acid has different chemical and physical properties, owing to the slightly different bond configuration. It has a much higher melting point, 45 [[Celsius | °C]], than oleic acid, 13.4 °C, due to the ability of the trans molecules to pack more tightly, forming a solid that is more difficult to break apart. This notably means that it is a solid at human body temperatures. Catalytic partial hydrogenation necessarily produces ''trans''-fats, because of the [[Hydrogenation#Heterogeneous catalysis | reaction mechanism]]. In the first reaction step, one hydrogen is added, with the other, coordinatively unsaturated, carbon being attached to the catalyst. The second step is the addition of hydrogen to the remaining carbon, producing a saturated fatty acid. The first step is reversible, such that the hydrogen is readsorbed on the catalyst and the double bond is re-formed. The intermediate with only one hydrogen added contains no double bond and can freely rotate. Thus, the double bond can re-form as either ''cis'' or ''trans'', of which ''trans'' is favored, regardless the starting material. Complete hydrogenation also hydrogenates any produced ''trans'' fats to give saturated fats. Researchers at the [[United States Department of Agriculture]] have investigated whether hydrogenation can be achieved without the side effect of trans fat production. They varied the [[pressure]] under which the chemical reaction was conducted – applying 1400 [[Pascal (unit) | kPa]] (200 [[pound-force per square inch | psi]]) of pressure to soybean oil in a 2-liter vessel while heating it to between 140 °C and 170 °C. The standard 140 kPa (20 psi) process of hydrogenation produces a product of about 40% trans fatty acid by weight, compared to about 17% using the high-pressure method. Blended with unhydrogenated liquid soybean oil, the high-pressure-processed oil produced margarine containing 5 to 6% trans fat. Based on current U.S. labeling requirements (see below), the manufacturer could claim the product was free of trans fat. The level of trans fat may also be altered by modification of the temperature and the length of time during hydrogenation. Animal-based fats were once the only ''trans'' fats consumed, but by far the largest amount of ''trans'' fat consumed today is created by the processed food industry as a side effect of partially hydrogenating unsaturated plant fats (generally vegetable oils). These partially hydrogenated fats have displaced natural solid fats and liquid oils in many areas, the most notable ones being in the fast food, [[snack food]], fried food, and baked goods industries. Partially hydrogenated oils have been used in food for many reasons. Hydrogenation increases product [[shelf life]] and decreases refrigeration requirements. Many baked foods require semi-solid fats to suspend solids at room temperature; partially hydrogenated oils have the right consistency to replace animal fats such as butter and [[lard]] at lower cost. They are also an inexpensive alternative to other semi-solid oils such as [[palm oil]].{{citation needed | date=June 2015}} [[File:Triglyceride Hydrogenation&Isomerization V.1.png | thumb | 330px | right | Reaction scheme: By far the largest amount of ''trans'' fat consumed today is created by the processed food industry as a side effect of partially catalytic hydrogenation of unsaturated plant fats (generally vegetable oils) with ''cis'' carbon-carbon double bonds. These partially hydrogenated fats have displaced natural solid fats and liquid oils in many areas, the most notable ones being in the fast food, [[snack food]], fried food, and baked goods industries.]] Up to 45% of the total fat in those foods containing man-made ''trans'' fats formed by partially hydrogenating plant fats may be ''trans'' fat. Baking shortenings, unless reformulated, contain around 30% ''trans'' fats compared to their total fats. High-fat dairy products such as butter contain about 4%. Margarines not reformulated to reduce ''trans'' fats may contain up to 15% ''trans'' fat by weight, but some reformulated ones are less than 1% trans fat. It has been established that ''trans'' fats in human [[breast milk]] fluctuate with maternal consumption of trans fat, and that the amount of trans fats in the bloodstream of breastfed infants fluctuates with the amounts found in their milk. In 1999, reported percentages of trans fats (compared to total fats) in human milk ranged from 1% in Spain, 2% in France, 4% in Germany, and 7% in Canada and the United States. Trans fats are used in shortenings for deep-frying in restaurants, as they can be used for longer than most conventional oils before becoming rancid. In the early 21st century, non-hydrogenated vegetable oils that have lifespans exceeding that of the frying shortenings became available. As fast-food chains routinely use different fats in different locations, trans fat levels in fast food can have large variations. For example, an analysis of samples of [[McDonald's]] French fries collected in 2004 and 2005 found that fries served in New York City contained twice as much trans fat as in [[Hungary]], and 28 times as much as in [[Denmark]], where trans fats are restricted. At KFC, the pattern was reversed, with Hungary's product containing twice the trans fat of the New York product. Even within the United States there was variation, with fries in New York containing 30% more trans fat than those from [[Atlanta]]. ===Nutritional guidelines=== The [[United States National Academy of Sciences | National Academy of Sciences]] (NAS) advises the United States and Canadian governments on nutritional science for use in public policy and product labeling programs. Their 2002 ''Dietary Reference Intakes for Energy, Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids'' contains their findings and recommendations regarding consumption of trans fat ([http://www.nap.edu/openbook/0309085373/html/423.html summary]). Their recommendations are based on two key facts. First, "trans fatty acids are not essential and provide no known benefit to human health", whether of animal or plant origin. Second, while both saturated and trans fats increase levels of [[Low-density lipoprotein | LDL]], trans fats also lower levels of [[High-density lipoprotein | HDL]]; thus increasing the risk of coronary artery disease. The NAS is concerned "that dietary trans fatty acids are more deleterious with respect to coronary artery disease than saturated fatty acids". This analysis is supported by a 2006 [[New England Journal of Medicine]] (NEJM) scientific review that states "from a nutritional standpoint, the consumption of trans fatty acids results in considerable potential harm but no apparent benefit." Because of these facts and concerns, the NAS has concluded there is no safe level of trans fat consumption. There is no adequate level, recommended daily amount or tolerable upper limit for trans fats. This is because any incremental increase in trans fat intake increases the risk of coronary artery disease. Despite this concern, the NAS dietary recommendations have not included eliminating trans fat from the diet. This is because trans fat is naturally present in many animal foods in trace quantities, and thus its removal from ordinary diets might introduce undesirable side effects and nutritional imbalances if proper nutritional planning is not undertaken. The NAS has, thus, "recommended that trans fatty acid consumption be as low as possible while consuming a nutritionally adequate diet". Like the NAS, the [[World Health Organization]] has tried to balance public health goals with a practical level of trans fat consumption, recommending in 2003 that trans fats be limited to less than 1% of overall energy intake. The US National Dairy Council has asserted that the trans fats present in animal foods are of a different type than those in partially hydrogenated oils, and do not appear to exhibit the same negative effects. While a recent scientific review agrees with the conclusion (stating that "the sum of the current evidence suggests that the Public health implications of consuming trans fats from ruminant products are relatively limited"), it cautions that this may be due to the low consumption of trans fats from animal sources compared to artificial ones. More recent inquiry (independent of the dairy industry) has found in a 2008 Dutch meta-analysis that all trans fats, regardless of natural or artificial origin equally raise LDL and lower HDL levels. Other studies though have shown different results when it comes to animal based trans fats like conjugated linoleic acid (CLA). Although CLA is known for its anticancer properties, researchers have also found that the cis-9, trans-11 form of CLA can reduce the risk for cardiovascular disease and help fight inflammation. ===Health risks=== Partially hydrogenated vegetable oils have been an increasingly significant part of the human diet for about 100 years (in particular, since the later half of the 20th century and where more processed foods are consumed), and some deleterious effects of trans fat consumption are scientifically accepted, forming the basis of the health guidelines discussed above. The exact [[biochemistry | biochemical]] process by which trans fats produce specific health problems are a topic of continuing research. Intake of dietary trans fat perturbs the body's ability to metabolize [[essential fatty acid]]s (EFAs, including [[Omega-3 fatty acid | Omega-3]]) leading to changes in the phospholipid fatty acid composition of the arterial walls, thereby raising risk of coronary artery disease. While the mechanisms through which trans fatty acids contribute to coronary artery disease are fairly well understood, the mechanism for their effects on diabetes is still under investigation. They may impair the metabolism of long-chain polyunsaturated fatty acids (LCPUFAs), but maternal pregnancy trans fatty acid intake has been inversely associated with LCPUFAs levels in infants at birth thought to underlie the positive association between breastfeeding and intelligence. High intake of trans fatty acids can lead to many health problems throughout one's life. They are abundant in fast food restaurants. They are consumed in greater quantities by people who lack access to a diet consisting of fewer hydrogenated fats, or who often consume fast food. A diet high in trans fats can contribute to obesity, high blood pressure, and higher risk for heart disease{{citation needed | date=May 2014}}. Trans fat has also been implicated in the development of Type 2 diabetes. ====Coronary artery disease==== The primary health risk identified for trans fat consumption is an elevated risk of [[coronary artery disease]] (CAD). A 1994 study estimated that over 30,000 cardiac deaths per year in the United States are attributable to the consumption of trans fats. By 2006 upper estimates of 100,000 deaths were suggested. A comprehensive review of studies of trans fats published in 2006 in the [[New England Journal of Medicine]] reports a strong and reliable connection between trans fat consumption and CAD, concluding that "On a per-calorie basis, trans fats appear to increase the risk of CAD more than any other macronutrient, conferring a substantially increased risk at low levels of consumption (1 to 3% of total energy intake)". The major evidence for the effect of trans fat on CAD comes from the [[Nurses' Health Study]] – a [[cohort study]] that has been following 120,000 female nurses since its inception in 1976. In this study, Hu and colleagues analyzed data from 900 coronary events from the study's [[statistical population | population]] during 14 years of followup. He determined that a nurse's CAD risk roughly doubled ([[relative risk]] of 1.93, [[confidence interval | CI]]: 1.43 to 2.61) for each 2% increase in trans fat calories consumed (instead of carbohydrate calories). By contrast, for each 5% increase in saturated fat calories (instead of carbohydrate calories) there was a 17% increase in risk ([[relative risk]] of 1.17, [[confidence interval | CI]]: 0.97 to 1.41). "The replacement of saturated fat or trans unsaturated fat by cis (unhydrogenated) unsaturated fats was associated with larger reductions in risk than an isocaloric replacement by carbohydrates." Hu also reports on the benefits of reducing trans fat consumption. Replacing 2% of [[food energy]] from trans fat with non-trans [[unsaturated fat]]s more than halves the risk of CAD (53%). By comparison, replacing a larger 5% of food energy from saturated fat with non-trans unsaturated fats reduces the risk of CAD by 43%. Another study considered deaths due to CAD, with consumption of trans fats being linked to an increase in mortality, and consumption of [[polyunsaturated fat]]s being linked to a decrease in mortality. There are two accepted tests that measure an individual's risk for coronary artery disease, both [[blood test]]s. The first considers [[ratio]]s of two types of [[cholesterol]], the other the amount of a cell-signalling [[cytokine]] called [[C-reactive protein]]. The ratio test is more accepted, while the cytokine test may be more powerful but is still being studied. The effect of trans fat consumption has been documented on each as follows: * Cholesterol ratio: This ratio compares the levels of [[low-density lipoprotein | LDL]] to [[High-density lipoprotein | HDL]]. Trans fat behaves like [[saturated fat]] by raising the level of LDL, but, unlike saturated fat, it has the additional effect of decreasing levels of HDL. The net increase in LDL/HDL ratio with trans fat is approximately double that due to saturated fat. (Higher ratios are worse.) One randomized [[crossover study]] published in 2003 comparing the effect [[postprandial | of eating a meal]] on blood lipids of (relatively) cis and trans fat rich meals showed that [[cholesteryl ester]] transfer (CET) was 28% higher after the trans meal than after the cis meal and that lipoprotein concentrations were enriched in [[apolipoprotein]](a) after the trans meals. * C-reactive protein (CRP): A study of over 700 nurses showed that those in the highest [[quartile]] of trans fat consumption had blood levels of CRP that were 73% higher than those in the lowest quartile. ====Other health risks==== There are suggestions that the negative consequences of trans fat consumption go beyond the cardiovascular risk. In general, there is much less scientific consensus asserting that eating trans fat specifically increases the risk of other chronic health problems: * [[Alzheimer's Disease]]: A study published in [[Archives of Neurology]] in February 2003 suggested that the intake of both trans fats and saturated fats promote the development of Alzheimer disease, although not confirmed in an animal model. It has been found that trans fats impaired memory and learning in middle-age rats. The trans-fat eating rats' brains had fewer proteins critical to healthy neurological function. Inflammation in and around the hippocampus, the part of the brain responsible for learning and memory. These are the exact types of changes normally seen at the onset of Alzheimer's, but seen after six weeks, even though the rats were still young. * [[Cancer]]: There is no scientific consensus that consuming trans fats significantly increases cancer risks across the board. The American Cancer Society states that a relationship between trans fats and cancer "has not been determined." One study has found a positive connection between trans fat and prostate cancer. However, a larger study found a correlation between trans fats and a significant decrease in high-grade prostate cancer. An increased intake of trans fatty acids may raise the risk of breast cancer by 75%, suggest the results from the French part of the European Prospective Investigation into Cancer and Nutrition. * [[Diabetes]]: There is a growing concern that the risk of [[diabetes mellitus type 2 | type 2 diabetes]] increases with trans fat consumption. However, consensus has not been reached. For example, one study found that risk is higher for those in the highest [[quartile]] of trans fat consumption. Another study has found no diabetes risk once other factors such as total fat intake and BMI were accounted for. * [[Obesity]]: Research indicates that trans fat may increase weight gain and abdominal fat, despite a similar caloric intake. A 6-year experiment revealed that monkeys fed a trans fat diet gained 7.2% of their body weight, as compared to 1.8% for monkeys on a mono-unsaturated fat diet. Although obesity is frequently linked to trans fat in the popular media, this is generally in the context of eating too many calories; there is not a strong scientific consensus connecting trans fat and obesity, although the 6-year experiment did find such a link, concluding that "under controlled feeding conditions, long-term TFA consumption was an independent factor in weight gain. TFAs enhanced intra-abdominal deposition of fat, even in the absence of caloric excess, and were associated with insulin resistance, with evidence that there is impaired post-insulin receptor binding signal transduction." * [[Liver function | Liver dysfunction]]: Trans fats are metabolized differently by the [[liver]] than other fats and interfere with delta 6 [[desaturase]]. Delta 6 desaturase is an [[enzyme]] involved in converting essential fatty acids to [[arachidonic acid]] and [[prostaglandin]]s, both of which are important to the functioning of cells. * [[Female infertility | Infertility in women]]: One 2007 study found, "Each 2% increase in the intake of energy from trans unsaturated fats, as opposed to that from carbohydrates, was associated with a 73% greater risk of ovulatory infertility...". * [[Major depressive disorder]]: Spanish researchers analysed the diets of 12,059 people over six years and found that those who ate the most trans fats had a 48 per cent higher risk of depression than those who did not eat trans fats. One mechanism may be trans-fats' substitution for [[docosahexaenoic acid]] (DHA) levels in the [[orbitofrontal cortex]] (OFC). Very high intake of trans-fatty acids (43% of total fat) in mice from 2 to 16 months of age was associated with lowered DHA levels in the brain (p=0.001). When the brains of 15 major depressive subjects who had committed suicide were examined post-mortem and compared against 27 age-matched controls, the suicidal brains were found to have 16% less (male average) to 32% less (female average) DHA in the OFC. The OFC controls [[Reward (psychology) | reward]], reward expectation, and [[empathy]] (all of which are reduced in depressive mood disorders) and regulates the [[limbic system]]. * Behavioral [[irritability]] and [[aggression]]: a 2012 observational analysis of subjects of an earlier study found a strong relation between dietary trans fat acids and self-reported behavioral aggression and irritability, suggesting but not establishing causality. * Diminished [[memory]]: In a 2015 article, researchers re-analyzing results from the 1999-2005 UCSD Statin Study argue that "greater dietary trans fatty acid consumption is linked to worse word memory in adults during years of high productivity, adults age <45". * [[Acne]]: According to a 2015 study, trans fats are one of several components of [[Western pattern diet]]s which promote acne, along with [[carbohydrate]]s with high [[glycemic load]] such as [[white sugar | refined sugars]] or [[refined grains | refined starches]], [[milk]] and [[dairy product]]s, and [[saturated fat]]s, while [[omega-3 fatty acid]]s, which reduce acne, are deficient in Western pattern diets. ===Public response and regulation=== {{main | Trans fat regulation}} ==Nutritional and health aspects== The benefits and risks of dietary fats have been the object of much study, and are still highly controversial topics. ===Essential fatty acids=== There are two [[essential fatty acids]] (EFAs) in human nutrition: [[Alpha-Linolenic acid | alpha-linolenic acid]] (an [[omega-3 fatty acid]]) and [[linoleic acid]] (an [[omega-6 fatty acid]]). Other lipids needed by the body can be synthesized from these and other fats. ===Saturated vs. unsaturated fats=== Studies have found that replacing saturated fats with ''cis'' unsaturated fats in the diet reduces risk of cardiovascular disease. For example, a 2020 systematic review of randomized control trials by the [[Cochrane Library]] concluded: "Lifestyle advice to all those at risk of cardiovascular disease and to lower risk population groups should continue to include permanent reduction of dietary saturated fat and partial replacement by unsaturated fats." ===''Cis'' vs. ''trans'' fats=== Numerous studies have also found that consumption of ''trans'' fats increases risk of cardiovascular disease. The [[Harvard School of Public Health]] advises that replacing ''trans'' fats and saturated fats with ''cis'' monounsaturated and polyunsaturated fats is beneficial for health. [https://www.hsph.harvard.edu/nutritionsource/what-should-you-eat/fats-and-cholesterol/ "Fats and Cholesterol"], ''Harvard School of Public Health''. Retrieved 02-11-16. In the last few decades, there has been substantial amount of [[trans fat regulation | regulation of trans fats]] in industrialized and commercial food products. ===Interesterification=== Some studies have investigated the health effects of insteresterified (IE) fats, by comparing diets with IE and non-IE fats with the same overall fatty acid composition. Several experimental studies in humans found no statistical difference on fasting blood lipids between a with large amounts of IE fat, having 25-40% C16:0 or C18:0 on the 2-position, and a similar diet with non-IE fat, having only 3-9% C16:0 or C18:0 on the 2-position. A negative result was obtained also in a study that compared the effects on blood [[cholesterol]] levels of an IE fat product mimicking [[cocoa butter]] and the real non-IE product. A 2007 study funded by the Malaysian Palm Oil Board claimed that replacing natural [[palm oil]] by other interesterified or partial hydrogenated fats caused adverse health effects, such as higher [[low-density lipoprotein | LDL]]/[[high-density lipoprotein | HDL]] ratio and [[plasma glucose level]]s. However, these effects could be attributed to the higher percentage of saturated acids in the IE and partially hydrogenated fats, rather than to the IE process itself. ==Fat digestion and metabolism== {{main | Lipid metabolism}} Fats are broken down in the healthy body to release their constituents, [[Glycerin | glycerol]] and [[fatty acid]]s. Glycerol itself can be converted to [[glucose]] by the liver and so become a source of energy. Fats and other lipids are broken down in the body by enzymes called [[lipase]]s produced in the [[pancreas]]. Many cell types can use either glucose or fatty acids as a source of energy for metabolism. In particular, heart and skeletal muscle prefer fatty acids.{{cn | date=August 2020}} Despite long-standing assertions to the contrary, fatty acids can also be used as a source of fuel for brain cells through mitochondrial oxidation. ==See also== * [[Animal fat]] * [[Carbohydrate]] * [[Dieting]] * [[Fat content of milk]] * [[Food composition data]] * [[Lipid]] * [[Omega-3 fatty acid]] * [[Omega-6 fatty acid]] * [[Trans fat]] * [[Vegetable oil]] * [[Yellow grease]] *[[List of saturated fatty acids]] *[[List of vegetable oils]] *[[Trans fat]] *[[Food groups]] *[[Food guide pyramid]] *[[Healthy diet]] *[[Diet and heart disease]] *[[Fast food]] *[[Junk food]] *[[Advanced glycation endproduct]] *[[ANGPTL4]] *[[Iodine value]] *[[Framingham Heart Study]] *[[Seven Countries Study]] *[[Ancel Keys]] *[[D. Mark Hegsted]] *[[Western pattern diet]] * [[Iodine value]] – a chemical analysis method to determine the proportion of unsaturated fat. * [[List of unsaturated fatty acids]] * [[High density lipoprotein]] * [[Saturated fat]] * [[Unsaturated fat]] * [[Polyunsaturated|Polyunsaturated fat]] * [[Fatty acid synthesis]] ==Further reading== * * * * * == External links == * * * * * * * * {{Cookbook | Oil and fat}} {{wiktionary | Fat}} ==References== Entry for [https://www.merriam-webster.com/dictionary/fat "fat"] in the online Merriam-Webster disctionary, sense 3.2. Accessed on 2020-08-09 [https://www.bbc.co.uk/health/treatments/healthy_living/nutrition/healthy_fatsugar.shtml Fats and sugars]. 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[https://www.fda.gov/OHRMS/DOCKETS/98fr/03-17525.htm Federal Register – 68 FR 41433 11 July 2003: Food Labeling: Trans Fatty Acids in Nutrition Labeling, Nutrient Content Claims, and Health Claims] George A. 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https://www.fda.gov/ohrms/dockets/dockets/06q0458/06q-0458-sup0001-02.pdf | title = Dietary Guidelines for Americans | year = 2005}} {{cite book | last=Food and nutrition board, institute of medicine of the national academies | title=Dietary Reference Intakes for Energy, Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids (Macronutrients) | publisher=National Academies Press | year=2005 | pages=i | url=http://darwin.nap.edu/books/0309085373/html/R1.html | url-status=dead | archive-url=https://web.archive.org/web/20060918061042/http://darwin.nap.edu/books/0309085373/html/R1.html | archive-date=18 September 2006}} {{cite book | last=Food and nutrition board, institute of medicine of the national academies | title=Dietary Reference Intakes for Energy, Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids (Macronutrients) | publisher=National Academies Press | year=2005 | pages = 447 | url=http://darwin.nap.edu/books/0309085373/html/447.html}}{{dead link | date=January 2018 | bot=InternetArchiveBot | fix-attempted=yes}} {{cite book | last=Food and nutrition board, institute of medicine of the national academies | title=Dietary reference intakes for energy, carbohydrate, fiber, fat, fatty acids, cholesterol, protein, and amino acids (macronutrients) | publisher=National Academies Press | year=2005 | pages = 504 | url=http://darwin.nap.edu/books/0309085373/html/504.html}}{{dead link | date=September 2017 | bot=InternetArchiveBot | fix-attempted=yes}} {{cite book | last=Food and nutrition board, institute of medicine of the national academies | title=Dietary Reference Intakes for Energy, Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids (Macronutrients) | publisher=National Academies Press | year=2005 | pages = 424 | url=http://darwin.nap.edu/books/0309085373/html/424.html}}{{dead link | date=January 2018 | bot=InternetArchiveBot | fix-attempted=yes}} {{cite journal | vauthors = Lopez-Garcia E, Schulze MB, Meigs JB, Manson JE, Rifai N, Stampfer MJ, Willett WC, Hu FB | display-authors = 6 | title = Consumption of trans fatty acids is related to plasma biomarkers of inflammation and endothelial dysfunction | journal = The Journal of Nutrition | volume = 135 | issue = 3 | pages = 562–6 | date = March 2005 | pmid = 15735094 | doi = 10.1093/jn/135.3.562 | doi-access = free }} {{Cite web | url=http://www.iseo.org/foodfatsoils.pdf | title=Food Fats and oils | last=Institute of Shortenings and Edible oils | year=2006 | url-status=dead | archive-url=https://web.archive.org/web/20070326144952/http://www.iseo.org/foodfatsoils.pdf | archive-date=2007-03-26 | access-date=2009-02-19}} {{cite web | vauthors=Ascherio A, Stampfer MJ, Willett WC | title=Trans fatty acids and coronary heart disease | url=http://www.hsph.harvard.edu/reviews/transfats.html | access-date=14 September 2006 | archive-url=https://web.archive.org/web/20060903061226/http://www.hsph.harvard.edu/reviews/transfats.html | archive-date=3 September 2006}} {{cite journal | vauthors = Chavarro J, Stampfer M, Campos H, Kurth T, Willett W, Ma J | title=A prospective study of blood trans fatty acid levels and risk of prostate cancer | journal=Proc. 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Cancer Res. | volume=47 | date=1 April 2006 | url=http://www.aacrmeetingabstracts.org/cgi/content/abstract/2006/1/943 | access-date=9 January 2007 | issue=1 | pages = 943}} {{cite journal |vauthors=Corwin RL, Hartman TJ, Maczuga SA, Graubard BI | title = Dietary saturated fat intake is inversely associated with bone density in humans: Analysis of NHANES III | journal = The Journal of Nutrition | volume = 136 | issue = 1 | pages = 159–165 | year = 2006 | pmid = 16365076 | doi = 10.1093/jn/136.1.159 | s2cid = 4443420 | url = https://semanticscholar.org/paper/d7811ba4c3926bb0830ea4ad213eae7a21fe1889 }} {{cite journal | vauthors=Howard BV, Van Horn L, Hsia J, Manson JE, Stefanick ML, Wassertheil-Smoller S, Kuller LH, LaCroix AZ, Langer RD, Lasser NL, Lewis CE, Limacher MC, Margolis KL, Mysiw WJ, Ockene JK, Parker LM, Perri MG, Phillips L, [[Ross Prentice | Prentice RL]], Robbins J, Rossouw JE, Sarto GE, Schatz IJ, Snetselaar LG, Stevens VJ, Tinker LF, Trevisan M, Vitolins MZ, Anderson GL, Assaf AR, Bassford T, Beresford SA, Black HR, Brunner RL, Brzyski RG, Caan B, Chlebowski RT, Gass M, Granek I, Greenland P, Hays J, Heber D, Heiss G, Hendrix SL, Hubbell FA, Johnson KC, Kotchen JM | display-authors = 6 | title = Low-fat dietary pattern and risk of cardiovascular disease: the Women's Health Initiative Randomized Controlled Dietary Modification Trial | journal = Journal of the American Medical Association | volume = 295 | issue = 6 | pages = 655–66 | year = 2006 | pmid = 16467234 | doi = 10.1001/jama.295.6.655 | doi-access = free }} {{cite journal | author = [[Alice H. Lichtenstein|Lichtenstein AH]], Appel LJ, Brands M, Carnethon M, Daniels S, Franch HA, Franklin B, Kris-Etherton P, Harris WS, Howard B, Karanja N, Lefevre M, Rudel L, Sacks F, Van Horn L, Winston M, Wylie-Rosett J | title = Diet and lifestyle recommendations revision 2006: a scientific statement from the American Heart Association Nutrition Committee | journal = Circulation | volume = 114 | issue = 1 | pages = 82–96 | date = July 2006 | pmid = 16785338 | doi = 10.1161/CIRCULATIONAHA.106.176158 | s2cid = 647269 }} Dariush Mozaffarian, Martijn B. Katan, Alberto Ascherio, Meir J. Stampfer, and Walter C. Willett (2006): "Trans fatty acids and cardiovascular disease". 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url=http://www.hc-sc.gc.ca/hl-vs/iyh-vsv/food-aliment/trans-eng.php | website=It's your health | publisher=Health Canada | title=Trans fat | date=Dec 2007 | url-status=dead | archive-url=https://web.archive.org/web/20120420052235/http://www.hc-sc.gc.ca/hl-vs/iyh-vsv/food-aliment/trans-eng.php | archive-date=20 April 2012}} {{cite journal | vauthors = Kavanagh K, Jones KL, Sawyer J, Kelley K, Carr JJ, Wagner JD, Rudel LL | title = Trans fat diet induces abdominal obesity and changes in insulin sensitivity in monkeys | journal = Obesity | volume = 15 | issue = 7 | pages = 1675–84 | date = July 2007 | pmid = 17636085 | doi = 10.1038/oby.2007.200 }} {{cite journal |vauthors=Lewington S, Whitlock G, Clarke R, Sherliker P, Emberson J, Halsey J, Qizilbash N, Peto R, Collins R | title = Blood cholesterol and vascular mortality by age, sex, and blood pressure: a meta-analysis of individual data from 61 prospective studies with 55,000 vascular deaths | journal = Lancet | volume = 370 | issue = 9602 | pages = 1829–39 | date = December 2007 | pmid = 18061058 | doi = 10.1016/S0140-6736(07)61778-4 | s2cid = 54293528 | url = | issn = }} {{cite journal | vauthors = Martin CA, Milinsk MC, Visentainer JV, Matsushita M, de-Souza NE | title = Trans fatty acid-forming processes in foods: a review | journal = Anais da Academia Brasileira de Ciencias | volume = 79 | issue = 2 | pages = 343–50 | date = June 2007 | pmid = 17625687 | doi = 10.1590/S0001-37652007000200015 | doi-access = free }} {{cite journal | vauthors = McNamara RK, Hahn CG, Jandacek R, Rider T, Tso P, Stanford KE, Richtand NM | title = Selective deficits in the omega-3 fatty acid docosahexaenoic acid in the postmortem orbitofrontal cortex of patients with major depressive disorder | journal = Biological Psychiatry | volume = 62 | issue = 1 | pages = 17–24 | date = July 2007 | pmid = 17188654 | doi = 10.1016/j.biopsych.2006.08.026 | url = http://www.biologicalpsychiatryjournal.com/article/S0006-3223(06)01065-1/abstract }} 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SE, Woodward R, Yeoh C, Miller GJ, Sanders TA}} {{cite journal |vauthors=Kris-Etherton PM, Innis S | title = Position of the American Dietetic Association and Dietitians of Canada: Dietary Fatty Acids | journal = Journal of the American Dietetic Association | volume = 107 | issue = 9 | pages = 1599–1611 [1603] | date = September 2007 | pmid = 17936958 | doi = 10.1016/j.jada.2007.07.024}} {{cite journal | vauthors = Willett WC | title = The role of dietary n-6 fatty acids in the prevention of cardiovascular disease | journal = Journal of Cardiovascular Medicine | volume = 8 Suppl 1 | issue = | pages = S42-5 | date = September 2007 | pmid = 17876199 | doi = 10.2459/01.JCM.0000289275.72556.13 }} {{cite web | title=Trans fat: Avoid this cholesterol double whammy | publisher=Mayo Foundation for Medical Education and Research (MFMER) | url=http://www.mayoclinic.com/health/trans-fat/CL00032 | access-date=10 December 2007}} {{cite book | title=Handbook of chemistry and physics | url=http://www.hbcpnetbase.com | access-date=19 November 2007 | edition=88th | series=2007–2008 | year=2007 | publisher=Taylor and Francis | chapter=Section 7: Biochemistry | chapterurl=http://www.hbcpnetbase.com/articles/07_05_86.pdf}} {{cite journal | vauthors = Chavarro JE, Rich-Edwards JW, Rosner BA, Willett WC | title = Dietary fatty acid intakes and the risk of ovulatory infertility | journal = The American Journal of Clinical Nutrition | volume = 85 | issue = 1 | pages = 231–7 | date = January 2007 | pmid = 17209201 | doi = 10.1093/ajcn/85.1.231 | doi-access = free }} {{cite journal | vauthors = Chajès V, Thiébaut AC, Rotival M, Gauthier E, Maillard V, Boutron-Ruault MC, Joulin V, Lenoir GM, Clavel-Chapelon F | display-authors = 6 | title = Association between serum trans-monounsaturated fatty acids and breast cancer risk in the E3N-EPIC Study | journal = American Journal of Epidemiology | volume = 167 | issue = 11 | pages = 1312–20 | date = June 2008 | pmid = 18390841 | pmc = 2679982 | doi = 10.1093/aje/kwn069 }} {{cite journal |vauthors=Crowe FL, Allen NE, Appleby PN, Overvad K, Aardestrup IV, Johnsen NF, Tjønneland A, Linseisen J, Kaaks R, Boeing H, Kröger J, Trichopoulou A, Zavitsanou A, Trichopoulos D, Sacerdote C, Palli D, Tumino R, Agnoli C, Kiemeney LA, Bueno-de-Mesquita HB, Chirlaque MD, Ardanaz E, Larrañaga N, Quirós JR, Sánchez MJ, González CA, Stattin P, Hallmans G, Bingham S, Khaw KT, Rinaldi S, Slimani N, Jenab M, Riboli E, Key TJ | title = Fatty acid composition of plasma phospholipids and risk of prostate cancer in a case-control analysis nested within the European Prospective Investigation into Cancer and Nutrition | journal = The American Journal of Clinical Nutrition | volume = 88 | issue = 5 | pages = 1353–63 | date = November 2008 | pmid = 18996872 | url = https://academic.oup.com/ajcn/article/88/5/1353/4649012| doi = 10.3945/ajcn.2008.26369 | doi-broken-date = 2020-08-23 }} {{cite book | editor1-last=Dijkstra | editor1-first=Albert | 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