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Encyclopedia > Fatty acid
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In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. Carboxylic acids as short as butyric acid (4 carbon atoms) are considered to be fatty acids, whereas fatty acids derived from natural fats and oils may be assumed to have at least 8 carbon atoms, e.g., caprylic acid (octanoic acid). Most of the natural fatty acids have an even number of carbon atoms, because their biosynthesis involves acetyl-CoA, a coenzyme carrying a two-carbon-atom group (see fatty acid synthesis). Fats is the plural for fat, a generic term for a class of lipids in biochemistry. ... Image File history File links Portal. ... For other uses, see Chemistry (disambiguation). ... Wöhler observes the synthesis of urea. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... In chemistry, non-aromatic and non-cyclic (acyclic) organic compounds are called aliphatic. ... When chain refers to a sequence, it can refer to: A chain of islands such as in an archipelago A chain of molecules such as in Nylon A chain of hills or mountains such as would form a mountain range Terms which use the term chain to refer to a... In chemistry, saturation has four different meanings: In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of that substance will appear as a precipitate. ... A unsaturated compound in chemistry is a chemical compound that contains carbon - carbon pi bonds such as a alkene or a alkyne. ... Butyric acid, (from Greek βουτυρος = butter) IUPAC name n-Butanoic acid, or normal butyric acid, is a carboxylic acid with structural formula CH3CH2CH2-COOH. It is notably found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). ... For other uses, see Carbon (disambiguation). ... For other uses, see Atom (disambiguation). ... Fats is the plural for fat, a generic term for a class of lipids in biochemistry. ... Oil painting is done on surfaces with pigment ground into a medium of oil - especially in early modern Europe, linseed oil. ... Caprylic acid is the common name for the eight-carbon straight chain fatty acid known by the systematic name octanoic acid. ... Biosynthesis is a phenomenon where chemical compounds are produced from simpler reagents. ... Categories: Biochemistry stubs | Thiols ... Coenzyme A Coenzymes are small organic non-protein molecules that carry chemical groups between enzymes. ... Fatty acids are formed by the action of Fatty acid synthases from acetyl-CoA and malonyl-CoA precursors. ...


In industry, fatty acids are produced by the hydrolysis of the ester linkages in a fat or biological oil (both of which are triglycerides), with the removal of glycerol. See oleochemicals. Hydrolysis is a chemical reaction or process in which a chemical compound is broken down by reaction with water. ... For other uses, see Ester (disambiguation). ... For other uses, see FAT. Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water. ... {{refimprove|date=October 2007} Ausra yra maza mergaite. ... Glycerine, Glycerin redirects here. ... Oleochemicals are chemicals derived from biological oils or fats. ...

Contents

Definition

Fatty acids are aliphatic monocarboxylic acids, derived from, or contained in esterified form in an animal or vegetable fat, oil or wax. Natural fatty acids commonly have a chain of 4 to 28 carbons (usually unbranched and even numbered), which may be saturated or unsaturated. By extension, the term is sometimes used to embrace all acyclic aliphatic carboxylic acids.[1]


Types

Three dimensional representations of several fatty acids
Three dimensional representations of several fatty acids

Fatty acids can be saturated and unsaturated, depending on double bonds. In addition, they also differ in length. Image of several fatty acid molecules created by me with POV-ray. ... Image of several fatty acid molecules created by me with POV-ray. ... Covalent bonding is a form of chemical bonding characterized by the sharing of one or more pairs of electrons between atoms, in order to produce a mutual attraction, which holds the resultant molecule together. ...


Saturated fatty acids

Saturated fatty acids do not contain any double bonds or other functional groups along the chain. The term "saturated" refers to hydrogen, in that all carbons (apart from the carboxylic acid [-COOH] group) contain as many hydrogens as possible. In other words, the omega (ω) end contains 3 hydrogens (CH3-), and each carbon within the chain contains 2 hydrogen atoms. Covalent bonding is a form of chemical bonding characterized by the sharing of one or more pairs of electrons between atoms, in order to produce a mutual attraction, which holds the resultant molecule together. ... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... This article is about the chemistry of hydrogen. ...


Saturated fatty acids form straight chains and, as a result, can be packed together very tightly, allowing living organisms to store chemical energy very densely. The fatty tissues of animals contain large amounts of long-chain saturated fatty acids. In IUPAC nomenclature, fatty acids have an [-oic acid] suffix. In common nomenclature, the suffix is usually -ic. IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A naming convention is an attempt to systematize names in a field so they unambiguously convey similar information in a similar manner. ...


The shortest descriptions of fatty acids include only the number of carbon atoms and double bonds in them (e.g., C18:0 or 18:0). C18:0 means that the carbon chain of the fatty acid consists of 18 carbon atoms, and there are no (zero) double bonds in it, whereas C18:1 describes an 18-carbon chain with one double bond in it. Each double bond can be in either a cis- or trans- conformation, and stands in a different position with respect to the ends of the fatty acid; therefore, not all C18:1s (for example) are identical. If there is one or more double bonds in the fatty acid, it is no longer considered saturated, but rather, mono- or polyunsaturated. A spacefilling model of the Stearic Acid molecule A diagram of the Stearic Acid molecule Stearic acid (IUPAC systematic name: octadecanoic acid) is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. ... Covalent redirects here. ... Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable sources. ... Covalent redirects here. ... Cis-2-butene Trans-2-butene In chemistry, geometric isomerism or cis-trans isomerism is a form of stereoisomerism and describes the orientation of functional groups within the molecule. ... Cis-2-butene Trans-2-butene In chemistry, geometric isomerism or cis-trans isomerism is a form of stereoisomerism and describes the orientation of functional groups within the molecule. ...


Most commonly-occurring saturated fatty acids are of the following varieties:

Common name IUPAC name Chemical structure Abbr. Melting point (°C)
Butyric Butanoic acid CH3(CH2)2COOH C4:0 -8
Caproic Hexanoic acid CH3(CH2)4COOH C6:0 -3
Caprylic Octanoic acid CH3(CH2)6COOH C8:0 16-17
Capric Decanoic acid CH3(CH2)8COOH C10:0 31
Lauric Dodecanoic acid CH3(CH2)10COOH C12:0 44-46
Myristic Tetradecanoic acid CH3(CH2)12COOH C14:0 58.8
Palmitic Hexadecanoic acid CH3(CH2)14COOH C16:0 63-64
Stearic Octadecanoic acid CH3(CH2)16COOH C18:0 69.9
Arachidic Eicosanoic acid CH3(CH2)18COOH C20:0 75.5
Behenic Docosanoic acid CH3(CH2)20COOH C22:0 74-78
Lignoceric Tetracosanoic acid CH3(CH2)22COOH C24:0

Butyric acid, (from Greek βουτυρος = butter) IUPAC name n-Butanoic acid, or normal butyric acid, is a carboxylic acid with structural formula CH3CH2CH2-COOH. It is notably found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). ... Hexanoic acid, also known as caproic acid, is the carboxylic acid derived from hexane with the formula C5H11COOH. It is a colorless oily liquid smelling of cheese. ... Caprylic acid is the common name for the eight-carbon straight chain fatty acid known by the systematic name octanoic acid. ... Decanoic acid is a type of carboxylic acid. ... Lauric acid, or dodecanoic acid, is a saturated fatty acid with the structural formula CH3(CH2)10COOH . ... Myristic acid, also called Tetradecanoic acid, is a common saturated fatty acid found in dairy products. ... Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated fatty acids found in animals and plants. ... A spacefilling model of the Stearic Acid molecule A diagram of the Stearic Acid molecule Stearic acid (IUPAC systematic name: octadecanoic acid) is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. ... Arachidic acid also called eicosanoic acid is a saturated fatty acid found in peanut oil. ... Behenic acid, also docosanoic acid, is a normal carboxylic acid, a fatty acid with formula C21H43COOH. In appearance, it consists of white to cream color crystals or powder with a melting point of 74-78°C and boiling point of 306°C. At 9%, it is a major component of... Lignoceric acid, also tetracosanoic acid, is a saturated fatty acid with formula C23H47COOH. Lignoceric acid is a byproduct of lignin production. ...

Unsaturated fatty acids

Comparison of the trans isomer (top) and the cis-isomer of oleic acid.
Comparison of the trans isomer (top) and the cis-isomer of oleic acid.

Unsaturated fatty acids are of similar form, except that one or more alkenyl functional groups exist along the chain, with each alkene substituting a single-bonded " -CH2-CH2-" part of the chain with a double-bonded "-CH=CH-" portion (that is, a carbon double-bonded to another carbon). Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable sources. ... The chemical structure of ethylene, the simplest alkene. ... A chemical bond is the physical process responsible for the attractive interactions between atoms and molecules, and that which confers stability to diatomic and polyatomic chemical compounds. ... Covalent redirects here. ...


The two next carbon atoms in the chain that are bound to either side of the double bond can occur in a cis or trans configuration. CIS usually refers to: Commonwealth of Independent States, a modern-day political entity consisting of 11 former Soviet Union Republics CIS is also an acronym for: Canadian Interuniversity Sport Cancer Information Service Carcinoma in situ Centre for Independent Studies Center for Immigration Studies Chinese International School Cisalpino Citizenship & Immigration Services... Trans is a Latin noun or prefix, meaning across, beyond or on the opposite side [of] . It is the opposite of cis, which means on the same side [of]. In chemistry, a double bond (or ring) not subject to free rotation in which the greater radical on both ends is...

cis 
A cis configuration means that adjacent carbon atoms are on the same side of the double bond. The rigidity of the double bond freezes its conformation and, in the case of the cis isomer, causes the chain to bend and restricts the conformational freedom of the fatty acid. The more double bonds the chain has in the cis configuration, the less flexibility it has. When a chain has many cis bonds, it becomes quite curved in its most accessible conformations. For example, oleic acid, with one double bond, has a "kink" in it, whereas linoleic acid, with two double bonds, has a more pronounced bend. Alpha-linolenic acid, with three double bonds, favors a hooked shape. The effect of this is that, in restricted environments, such as when fatty acids are part of a phospholipid in a lipid bilayer, or triglycerides in lipid droplets, cis bonds limit the ability of fatty acids to be closely packed, and therefore could affect the melting temperature of the membrane or of the fat.
trans 
A trans configuration, by contrast, means that the next two carbon atoms are bound to opposite sides of the double bond. As a result, they do not cause the chain to bend much, and their shape is similar to straight saturated fatty acids.

In most naturally-occurring unsaturated fatty acids, each double bond has 3n carbon atoms after it, for some n, and all are cis bonds. Most fatty acids in the trans configuration (trans fats) are not found in nature and are the result of human processing (e.g., hydrogenation). Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable sources. ... Linoleic acid (LA) is an unsaturated omega-6 fatty acid. ... Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. ... Hydrogenation is a class of chemical reactions which result an addition of hydrogen (H2) usually to unsaturated organic compounds. ...


The differences in geometry between the various types of unsaturated fatty acids, as well as between saturated and unsaturated fatty acids, play an important role in biological processes, and in the construction of biological structures (such as cell membranes).


Nomenclature

There are several different systems of nomenclature in use for unsaturated fatty acids. The following table describes the most common systems. A unsaturated compound in chemistry is a chemical compound that contains carbon - carbon pi bonds such as a alkene or a alkyne. ...

System Example Explanation
Trivial nomenclature Palmitoleic acid Trivial names (or common names) are non-systematic historical names which are the most frequent naming system used in literature. Most common fatty acids have trivial names in addition to their systematic names (see below). These names do not follow any pattern, but are concise and generally unambiguous.
Systematic nomenclature (9Z)-octadec-9-enoic acid Systematic names (or IUPAC names) derive from the standard IUPAC Rules for the Nomenclature of Organic Chemistry, published in 1979,[2] along with a recommendation published specifically for lipids in 1977.[3] Counting begins from the carboxylic acid end. Double bonds are labelled with cis-/trans- notation or E-/Z- notation, where appropriate. This notation is generally more verbose than common nomenclature, but has the advantage of being more technically clear and descriptive.
Δx nomenclature cis,cis912 In Δx (or delta-x) nomenclature, each double bond is indicated by Δx, where the double bond is located on the xth carbon–carbon bond, counting from the carboxylic acid end. Each double bond is preceded by a cis- or trans- prefix, indicating the conformation of the molecule around the bond. For example, linoleic acid is designated .
nx nomenclature n−3 nx (n minus x; also ω−x or omega-x) nomenclature does not provide names for individual compounds, but is a shorthand way to categorize fatty acids by their physiological properties. A double bond is located on the xth carbon–carbon bond, counting from the terminal methyl carbon (designated as n or ω) toward the carbonyl carbon. For example, α-Linolenic acid is classified as a n−3 or omega-3 fatty acid, and so it shares properties with other compounds of this type. The ω−x or omega-x notation is common in popular literature, but IUPAC has deprecated it in favor of nx notation in technical documents.[2] The most commonly researched fatty acid types are n−3 and n−6, which have unique biological properties.
Lipid numbers 18:3
18:3, n−6
18:3, cis,cis,cis-Δ91215
Lipid numbers take the form C:D, where C is the number of carbon atoms in the fatty acid and D is the number of double bonds in the fatty acid. This notation is ambiguous, as different fatty acids can have the same numbers. Consequently, this notation is usually paired with either a Δx or nx term.[2]

Examples of unsaturated fatty acids: Palmitoleic acid, or (Z)-9-hexadecenoic acid, is a monounsaturated fatty acid that is a common constituent of the glycerides of human adipose tissue. ... In chemistry, a trivial name (also common or vernacular name) is a non-systematic name. ... Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable sources. ... There are millions of possible objects that can be described in science, too many to create common names for every one. ... The IUPAC nomenclature of organic chemistry is a systematic method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... Covalent bonding is a form of chemical bonding characterized by the sharing of one or more pairs of electrons between atoms, in order to produce a mutual attraction, which holds the resultant molecule together. ... Cis-2-butene Trans-2-butene In chemistry, geometric isomerism or cis-trans isomerism is a form of stereoisomerism and describes the orientation of functional groups at the ends of a bond around which no rotation is possible. ... Cis-2-butene Trans-2-butene In chemistry, geometric isomerism or cis-trans isomerism is a form of stereoisomerism and describes the orientation of functional groups at the ends of a bond around which no rotation is possible. ... The more complex stereochemistry of highly substituted alkenes (especially 3 or 4 substituents) cannot be defined using the cis-trans notation. ... The more complex stereochemistry of highly substituted alkenes (especially 3 or 4 substituents) cannot be defined using the cis-trans notation. ... Linoleic acid (LA) is an unsaturated omega-6 fatty acid. ... Cis-2-butene Trans-2-butene In chemistry, geometric isomerism or cis-trans isomerism is a form of stereoisomerism and describes the orientation of functional groups at the ends of a bond around which no rotation is possible. ... Cis-2-butene Trans-2-butene In chemistry, geometric isomerism or cis-trans isomerism is a form of stereoisomerism and describes the orientation of functional groups at the ends of a bond around which no rotation is possible. ... Linoleic acid (LA) is an unsaturated omega-6 fatty acid. ... For an explanation of n and numerical nomenclature (such as n−3 or 18:3), see Nomenclature of fatty acids. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e. ... Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. ... For an explanation of n and numerical nomenclature (such as n−3 or 18:3), see Nomenclature of fatty acids. ... Omega-3 fatty acids are polyunsaturated fatty acids found in certain fish tissues, and in vegetable sources such as flax seeds, walnuts, and canola oil. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... For an explanation of n and numerical nomenclature (such as n−3 or 18:3), see Nomenclature of fatty acids. ... Omega-6 fatty acids are fatty acids where the term omega-6 signifies that the first double bond in the carbon backbone of the fatty acid, counting from the end opposite the acid group, occurs in the sixth carbon-carbon bond. ... gamma-Linolenic acid (GLA) is an omega-6 essential fatty acid found primarily in vegetable oils. ... Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. ...

Common name Chemical structure Δx C:D nx
Myristoleic acid CH3(CH2)3CH=CH(CH2)7COOH cis9 14:1 n−5
Palmitoleic acid CH3(CH2)5CH=CH(CH2)7COOH cis9 16:1 n−7
Oleic acid CH3(CH2)7CH=CH(CH2)7COOH cis9 18:1 n−9
Linoleic acid CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH cis,cis912 18:2 n−6
α-Linolenic acid CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH cis,cis,cis91215 18:3 n−3
Arachidonic acid CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOHNIST cis,cis,cis,cis5Δ81114 20:4 n−6
Eicosapentaenoic acid CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH cis,cis,cis,cis,cis58111417 20:5 n−3
Erucic acid CH3(CH2)7CH=CH(CH2)11COOH cis13 22:1 n−9
Docosahexaenoic acid CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)2COOH cis,cis,cis,cis,cis,cis4710131619 22:6 n−3

Palmitoleic acid, or (Z)-9-hexadecenoic acid, is a monounsaturated fatty acid that is a common constituent of the glycerides of human adipose tissue. ... Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable sources. ... Omega-9 fatty acids are a class of unsaturated fatty acids which have a C=C double bond in the ω-9 position. ... Linoleic acid (LA) is an unsaturated omega-6 fatty acid. ... Omega-6 fatty acids are fatty acids where the term omega-6 signifies that the first double bond in the carbon backbone of the fatty acid, counting from the end opposite the acid group, occurs in the sixth carbon-carbon bond. ... Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. ... For an explanation of n and numerical nomenclature (such as n−3 or 18:3), see Nomenclature of fatty acids. ... Arachidonic acid (AA) is an omega-6 fatty acid 20:4(ω-6). ... Omega-6 fatty acids are fatty acids where the term omega-6 signifies that the first double bond in the carbon backbone of the fatty acid, counting from the end opposite the acid group, occurs in the sixth carbon-carbon bond. ... Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an omega-3 fatty acid. ... For an explanation of n and numerical nomenclature (such as n−3 or 18:3), see Nomenclature of fatty acids. ... Erucic acid Erucic acid is a fatty acid found in rapeseed, wallflower seed, and mustard seed, making up 40 to 50 percent of their oil. ... Omega-9 fatty acids are a class of unsaturated fatty acids which have a C=C double bond in the ω-9 position. ... Docosahexaenoic acid (commonly known as DHA; 22:6(ω-3), all-cis-docosa-4,7,10,13,16,19-hexaenoic acid; trivial name cervonic acid) is an omega-3 essential fatty acid. ... For an explanation of n and numerical nomenclature (such as n−3 or 18:3), see Nomenclature of fatty acids. ...

Essential fatty acids

Main article: Essential fatty acid

The human body can produce all but two of the fatty acids it needs. These two, linoleic acid (AA acid) and alpha-linolenic acid (ALA), are widely distributed in plant oils. In addition, fish oils contain the longer-chain omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Other marine oils, such as from seal, also contain significant amounts of docosapentaenoic acid (DPA), which is also an omega-3 fatty acid. Although the body to some extent can convert LA and LNA into these longer-chain omega-3 fatty acids, the omega-3 fatty acids found in marine oils help fulfill the requirement of essential fatty acids (and have been shown to have wholesome properties of their own). Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism from other components (generally all references are to humans) by any known chemical pathways; and therefore must be obtained from the diet. ... Linoleic acid (LA) is an unsaturated omega-6 fatty acid. ... Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. ... Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an omega-3 fatty acid. ... Docosahexaenoic acid (commonly known as DHA; 22:6(ω-3), all-cis-docosa-4,7,10,13,16,19-hexaenoic acid; trivial name cervonic acid) is an omega-3 essential fatty acid. ... Docosapentaenoic acid designates any straight chain 22:5 fatty acid. ...


Since they cannot be made in the body from other substrates and must be supplied in food, they are called essential fatty acids. Mammals lack the ability to introduce double bonds in fatty acids beyond carbons 9 and 10. Hence linoleic acid and alpha-linolenic acid are essential fatty acids for humans.


In the body, essential fatty acids are primarily used to produce hormone-like substances that regulate a wide range of functions, including blood pressure, blood clotting, blood lipid levels, the immune response, and the inflammation response to injury infection.


Essential fatty acids are polyunsaturated fatty acids and are the parent compounds of the omega-6 and omega-3 fatty acid series, respectively. They are essential in the human diet because there is no synthetic mechanism for them. Humans can easily make saturated fatty acids or monounsaturated fatty acids with a double bond at the omega-9 position, but do not have the enzymes necessary to introduce a double bond at the omega-3 position or omega-6 position.


The essential fatty acids are important in several human body systems, including the immune system and in blood pressure regulation, since they are used to make compounds such as prostaglandins. The brain has increased amounts of linolenic and alpha-linoleic acid derivatives. Changes in the levels and balance of these fatty acids due to a typical Western diet rich in omega-6 and poor in omega-3 fatty acids is alleged"Study Links Brain Fatty Acid Levels To Depression", ScienceDaily, Bethesda, MD: American Society For Biochemistry And Molecular Biology, 2005-05-25. Retrieved on 2008-01-18.  to be associated with depression and behavioral change, including violence. The actual connection, if any, is still under investigation. Further, changing to a diet richer in omega-3 fatty acids, or consumption of supplements to compensate for a dietary imbalance, has been associated with reduced violent behavior[4] and increased attention span, but the mechanisms for the effect are still unclear. So far, at least three human studies have shown results that support this: two school studies[citation needed][5] as well as a double blind study in a prison.[4][6][7] E1 - Alprostadil I2 - Prostacyclin A prostaglandin is any member of a group of lipid compounds that are derived enzymatically from fatty acids and have important functions in the animal body. ... Year 2005 (MMV) was a common year starting on Saturday (link displays full calendar) of the Gregorian calendar. ... is the 145th day of the year (146th in leap years) in the Gregorian calendar. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... is the 18th day of the year in the Gregorian calendar. ... For other uses, see Depression. ...


Fatty acids play an important role in the life and death of cardiac cells because they are essential fuels for mechanical and electrical activities of the heart. [8] [9] [10] [11]


Trans fatty acids

Main article: Trans fat

A trans fatty acid (commonly shortened to trans fat) is an unsaturated fatty acid molecule that contains a trans double bond between carbon atoms, which makes the molecule less 'kinked' in comparison to fatty acids with cis double bonds. These bonds are characteristically produced during industrial hydrogenation of plant oils. Research suggests that amounts of trans fats correlate with circulatory diseases such as atherosclerosis and coronary heart disease more than the same amount of non-trans fats, for reasons that are not well understood. A trans fatty acid (commonly shortened to trans fat) is an unsaturated fatty acid molecule that contains a trans double bond between carbon atoms, which makes the molecule less kinked compared to cis fat. Research suggests a correlation between diets high in trans fats and diseases like atherosclerosis and coronary... For other uses, see Carbon (disambiguation). ... Coronary heart disease (CHD), also called coronary artery disease (CAD), ischaemic heart disease, atherosclerotic heart disease, is the end result of the accumulation of atheromatous plaques within the walls of the arteries that supply the myocardium (the muscle of the heart) with oxygen and nutrients. ...


Long and short

In addition to saturation, fatty acids are short, medium or long.

When discussing essential fatty acids, (EFA) a slightly different terminology applies. Short-chain EFA are 18 carbons long; long-chain EFA have 20 or more carbons.[13] Short chain fatty acids are a sub-group of fatty acids with aliphatic tails of less than six carbons. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid (or organic acid), often with a long aliphatic tail (long chains), either saturated or unsaturated. ... In chemistry, non-aromatic and non-cyclic (acyclic) organic compounds are called aliphatic. ... General Name, Symbol, Number Carbon, C, 6 Chemical series Nonmetals Group, Period, Block 14 (IVA), 2, p Density, Hardness 2267 kg/m3 0. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid (or organic acid), often with a long aliphatic tail (long chains), either saturated or unsaturated. ... In chemistry, non-aromatic and non-cyclic (acyclic) organic compounds are called aliphatic. ... General Name, Symbol, Number Carbon, C, 6 Chemical series Nonmetals Group, Period, Block 14 (IVA), 2, p Density, Hardness 2267 kg/m3 0. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid (or organic acid), often with a long aliphatic tail (long chains), either saturated or unsaturated. ... In chemistry, non-aromatic and non-cyclic (acyclic) organic compounds are called aliphatic. ... General Name, Symbol, Number Carbon, C, 6 Chemical series Nonmetals Group, Period, Block 14 (IVA), 2, p Density, Hardness 2267 kg/m3 0. ... Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism from other components (generally all references are to humans) by any known chemical pathways; and therefore must be obtained from the diet. ...


Free fatty acids

Fatty acids can be bound or attached to other molecules, such as in triglycerides or phospholipids. When they are not attached to other molecules, they are known as "free" fatty acids. {{refimprove|date=October 2007} Ausra yra maza mergaite. ... Phospholipid Two schematic representations of a phospholipid. ...


The uncombined fatty acids or free fatty acids may come from the breakdown of a triglyceride into its components (fatty acids and glycerol). However as fats are insoluble in water they must be bound to appropriate regions in the plasma protein albumin for transport around the body. The levels of "free fatty acid" in the blood are limited by the number of albumin binding sites available.


Free fatty acids are an important source of fuel for many tissues since they can yield relatively large quantities of ATP. Many cell types can use either glucose or fatty acids for this purpose. In particular, heart and skeletal muscle prefer fatty acids. The brain cannot use fatty acids as a source of fuel; it relies on glucose, or on ketone bodies. Ketone bodies are produced in the liver by fatty acid metabolism during starvation, or during periods of low carbohydrate intake. Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... Glucose (Glc), a monosaccharide (or simple sugar), is an important carbohydrate in biology. ... Ketone bodies are three chemicals that are produced as by-products when fatty acids are broken down for energy. ... This article or section is in need of attention from an expert on the subject. ...


Fatty acids in dietary fats

The following table gives the fatty acid, vitamin E and cholesterol composition of some common dietary fats.[14] [15]

Saturated Monounsaturated Polyunsaturated Cholesterol Vitamin E
g/100g g/100g g/100g mg/100g mg/100g
Animal fats
Lard 40.8 43.8 9.6 93 0.00
Butter 54.0 19.8 2.6 230 2.00
Vegetable fats
Coconut oil 85.2 6.6 1.7 0 .66
Palm oil 45.3 41.6 8.3 0 33.12
Cottonseed oil 25.5 21.3 48.1 0 42.77
Wheat germ oil 18.8 15.9 60.7 0 136.65
Soya oil 14.5 23.2 56.5 0 16.29
Olive oil 14.0 69.7 11.2 0 5.10
Corn oil 12.7 24.7 57.8 0 17.24
Sunflower oil 11.9 20.2 63.0 0 49.0 
Safflower oil 10.2 12.6 72.1 0 40.68
Rapeseed/Canola oil 5.3 64.3 24.8 0 22.21

This article is about the fat. ... For other uses, see Butter (disambiguation). ... Coconut oil, also known as coconut butter, is a tropical oil extracted from copra (the dried inner flesh of coconuts) with many applications. ... Palm oil from Ghana with its natural dark color visible, 2 litres Palm oil block showing the lighter color that results from boiling. ... Cottonseed oil is a vegetable oil extracted from the seeds of the cotton plant after the cotton lint has been removed. ... Wheat germ oil is extracted from the germ of the wheat kernel, which makes up only 2½% by weight of the kernel. ... This article or section contains information that has not been verified and thus might not be reliable. ... For the Popeye character, see Olive Oyl. ... Corn oil is oil extracted from the germ of corn. ... Sunflower Oil is the non-volatile oil expressed from sunflower (Helianthus annuus) seeds. ... Safflower oil is an oil extracted from the safflower seed. ... In agriculture, Canola is a trademarked cultivar of genetically engineered rapeseed variants from which rapeseed oil is obtained. ...

Acidity

Short chain carboxylic acids such as formic acid and acetic acid are miscible with water and dissociate to form reasonably strong acids (pKa 3.77 and 4.76, respectively). Longer-chain fatty acids do not show a great change in pKa. Nonanoic acid, for example, has a pKa of 4.96. However, as the chain length increases the solubility of the fatty acids in water decreases very rapidly, so that the longer-chain fatty acids have very little effect on the pH of a solution. The significance of their pKa values therefore has relevance only to the types of reactions in which they can take part. Formic acid (systematically called methanoic acid) is the simplest carboxylic acid. ... R-phrases , S-phrases , , , Flash point 43 °C Related Compounds Related carboxylic; acids Formic acid; Propionic acid; Butyric acid Related compounds acetamide; ethyl acetate; acetyl chloride; acetic anhydride; acetonitrile; acetaldehyde; ethanol; thioacetic acid; acetylcholine; acetylcholinesterase Supplementary data page Structure and properties n, εr, etc. ... An acid dissociation constant, denoted by Ka, is an equilibrium constant for the dissociation of a weak acid. ... Nonanoic acid, also called pelargonic acid, is an organic compound composed of a nine-carbon chain terminating in a carboxylic acid. ... For other uses, see PH (disambiguation). ...


Even those fatty acids that are insoluble in water will dissolve in warm ethanol, and can be titrated with sodium hydroxide solution using phenolphthalein as an indicator to a pale-pink endpoint. This analysis is used to determine the free fatty acid content of fats, i.e., the proportion of the triglycerides that have been hydrolyzed. Grain alcohol redirects here. ... This article is about volumetric titration. ... Sodium hydroxide (NaOH), also known as lye, caustic soda and (incorrectly, according to IUPAC nomenclature)[1] sodium hydrate, is a caustic metallic base. ... Phenolphthalein is a sensitive chemical with the formula C20H14O4 (often written as HIn in shorthand notation). ...


Reaction of fatty acids

Fatty acids react just like any other carboxylic acid, which means they can undergo esterification and acid-base reactions. Reduction of fatty acids yields fatty alcohols. Unsaturated fatty acids can also undergo addition reactions, most commonly hydrogenation, which is used to convert vegetable oils into margarine. With partial hydrogenation, unsaturated fatty acids can be isomerized from cis to trans configuration. In the Varrentrapp reaction certain unsaturated fatty acids are cleaved in molten alkali, a reaction at one time of relevance to structure elucidation. Esterification is the general name for a chemical reaction in which two chemicals (typically an alcohol and an acid) form an ester as the reaction product. ... The most fundamental reactions in chemistry are the redox processes. ... Fatty alcohols are aliphatic alcohols derived from natural fats and oils, originating in plants, but also synthesized in animals and algae. ... Hydrogenation is a class of chemical reactions which result an addition of hydrogen (H2) usually to unsaturated organic compounds. ...


Auto-oxidation and rancidity

Main article: Rancidification

Fatty acids at room temperature undergo a chemical change known as auto-oxidation. The fatty acid breaks down into hydrocarbons, ketones, aldehydes, and smaller amounts of epoxides and alcohols. Heavy metals present at low levels in fats and oils promote auto-oxidation. Fats and oils often are treated with chelating agents such as citric acid. Rancidification is the decomposition of fats and other lipids by hydrolysis and/or oxidation. ... Autoxidation is any oxidation that occurs in open air or in presence of oxygen and/or UV radiation and forms peroxides and hydroperoxides. ... Look up Hydrocarbon in Wiktionary, the free dictionary. ... Ketone group A ketone (pronounced as key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group. ... An aldehyde. ... An epoxide is a cyclic ether with only three ring atoms. ... This article does not cite any references or sources. ... Chelation (from Greek χηλή, chelè, meaning claw; pronounced ) is the binding or complexation of a bi- or multidentate ligand. ... Citric acid is a weak organic acid found in citrus fruits. ...


Circulation

Digestion and intake

Main article: Digestion#Fat digestion

Short- and medium chain fatty acids are absorbed directly into the blood via intestine capillaries and travel through the portal vein just as other absorbed nutrients do. However, long chain fatty acids are too large to be directly released into the tiny intestine capillaries. Instead they are absorbed into the fatty walls of the intestine villi and reassembled again into triglycerides. The triglycerides are coated with cholesterol and protein (protein coat) into a compound called a chylomicron. For the industrial process, see anaerobic digestion. ... Short chain fatty acids are a sub-group of fatty acids with aliphatic tails of less than six carbons. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... The portal vein is a major vein in the human body draining blood from the digestive system and its associated glands. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... Intestinal villi (singular: villus) are tiny, finger-like structures that protrude from the wall of the intestine and have additional extensions called microvilli (singular: microvillus) which protrude from epithelial cells lining villi. ... Triglyceride (blue: fatty acid; red: glycerol backbone) Triglycerides are glycerides in which the glycerol is esterified with three fatty acids. ... Cholesterol is a sterol (a combination steroid and alcohol). ... Chylomicrons are large lipoprotein particles (having a diameter of 75 to 1,200nm) that are created by the absorptive cells of the small intestine. ...


Within the villi, the chylomicron enters a lymphatic capillary called a lacteal, which merges into larger lymphatic vessels. It is transported via the lymphatic system and the thoracic duct up to a location near the heart (where the arteries and veins are larger). The thoracic duct empties the chylomicrons into the bloodstream via the left subclavian vein. At this point the chylomicrons can transport the triglycerides to where they are needed. In mammals including humans, the lymphatic vessels (or lymphatics) are a network of thin tubes that branch, like blood vessels, into tissues throughout the body. ... A lacteal is a lymphatic capillary that absorbs dietary fats in the villi of the small intestine. ... In human anatomy, the thoracic duct is an important part of the lymphatic system — it is the largest lymphatic vessel in the body. ... The subclavian vein is a continuation of the axillary vein and runs from the outer border of the first rib to the medial border of anterior scalene muscle. ...


Distribution

Main article: Blood fatty acids

Blood fatty acids are in different forms in different stages in the blood circulation. They are taken in through the intestine in chylomicrons, but also exist in very low density lipoproteins (VLDL) and low density lipoproteins (LDL) after processing in the liver. In addition, when released from adipocytes, fatty acids exist in the blood as free fatty acids. Chylomicrons are large lipoprotein particles (having a diameter of 75 to 1,200nm) that are created by the absorptive cells of the small intestine. ... Very Low Density Lipoprotein (VLDL) is a lipoprotein subclass. ... Low-density lipoprotein (LDL) belongs to the lipoprotein particle family. ... Adipose tissue is an anatomical term for loose connective tissue composed of energy in the form of fat, although it also cushions and insulates the body. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid (or organic acid), often with a long aliphatic tail (long chains), either saturated or unsaturated. ...


References

  1. ^ (1997) The Gold Book, 2nd, IUPAC Compendium of Chemical Terminology, International Union of Pure and Applied Chemistry. Retrieved on 2007-10-31. 
  2. ^ a b c Rigaudy, J.; Klesney, S.P. (1979). Nomenclature of Organic Chemistry. Pergamon. ISBN 0080223699. 
  3. ^ "The Nomenclature of Lipids. Recommendations, 1976" (1977) 79 (1): 11–21. doi:10.1111/j.1432-1033.1977.tb11778.x. 
  4. ^ a b C. Bernard Gesch, CQSW Sean M. Hammond, PhD Sarah E. Hampson, PhD Anita Eves, PhD Martin J. Crowder, PhD (2002). "Influence of supplementary vitamins, minerals and essential fatty acids on the antisocial behavior of young adult prisoners". The British Journal of Psychiatry 181: 22-28. Retrieved on 2006-06-27. 
  5. ^ Alexandra J. Richardson and Paul Montgomery (2005). "The Oxford-Durham study: a randomized controlled trial of dietary supplementation with fatty acids in children with developmental coordination disorder". Pediatrics 115 (5): 1360 - 1366. doi:10.1542/peds.2004-2164. Retrieved on 2006-06-27. 
  6. ^ Lawrence, Felicity (2004). in Kate Barker: Not on the Label. Penguin, 213. ISBN 0-14-101566-7. 
  7. ^ Using Fatty Acids for Enhancing Classroom Achievement. Retrieved on January, 2004.
  8. ^ E Honoré, J Barhanin, B Attali, F Lesage, and M Lazdunski (1994 March 1). "External blockade of the major cardiac delayed-rectifier K+ channel (Kv1.5) by polyunsaturated fatty acids.". Proc Natl Acad Sci U S A 91(5): 1937–1941. Retrieved on 2007-01-18.  - see page 1 of this link
  9. ^ Reiffel JA, McDonald A (2006). "Antiarrhythmic effects of omega-3 fatty acids". Am. J. Cardiol. 98 (4A): 50i–60i. doi:10.1016/j.amjcard.2005.12.027. PMID 16919517. Retrieved on 2007-12-04. 
  10. ^ Landmark K, Alm CS (2006). "Alpha-linolenic acid, cardiovascular disease and sudden death" (in Norwegian). Tidsskr. Nor. Laegeforen. 126 (21): 2792–4. PMID 17086218. Retrieved on 2007-12-04. 
  11. ^ Herbaut C (2006). "Omega-3 and health" (in French). Rev Med Brux 27 (4): S355–60. PMID 17091903. Retrieved on 2007-12-04. 
  12. ^ a b Short term effects of dietary medium-chain fatty acids and n-3 long-chain polyunsaturated fatty acids on the fat metabolism of healthy volunteers Christopher Beermann1 , J Jelinek1 , T Reinecker2 , A Hauenschild2 , G Boehm1 and H-U Klör2
  13. ^ Health Facts About Good Fats : The Basics : Omega-3s, Mono & Polyunsaturated Fatty Acids. Fats of Life Newsletter. Retrieved on 2007-12-12.
  14. ^ Food Standards Agency (1991). "Fats and Oils", McCance & Widdowson's The Composition of Foods. Royal Society of Chemistry. 
  15. ^ Ted Altar. More Than You Wanted To Know About Fats/Oils. Sundance Natural Foods Online. Retrieved on 2006-08-31.

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See also

Wikimedia Commons has media related to:

Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism from other components (generally all references are to humans) by any known chemical pathways; and therefore must be obtained from the diet. ... Saturated fat is fat that consists of triglycerides containing only saturated fatty acids. ... An unsaturated fat is a fat or fatty acid in which there are one or more double bonds in the fatty acid chain. ... Fatty acids are aliphatic acids fundamental to energy production and storage, cellular structure and as intermediates in the biosynthesis of hormones and other biologically important molecules. ... This article or section is in need of attention from an expert on the subject. ... A vegetable oil or vegoil is an oil extracted from oilseeds or another plant source. ...

External links

Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 280th day of the year (281st in leap years) in the Gregorian calendar. ... Some common lipids. ... Saturated fat is fat that consists of triglycerides containing only saturated fatty acids. ... Butyric acid, (from Greek βουτυρος = butter) IUPAC name n-Butanoic acid, or normal butyric acid, is a carboxylic acid with structural formula CH3CH2CH2-COOH. It is notably found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). ... Hexanoic acid, also known as caproic acid, is the carboxylic acid derived from hexane with the formula C5H11COOH. It is an oily liquid smelling of cheese. ... Caprylic acid is the common name for the eight-carbon straight chain fatty acid known by the systematic name octanoic acid. ... Decanoic acid is a type of carboxylic acid. ... Lauric acid, or dodecanoic acid, is a saturated fatty acid with the structural formula CH3(CH2)10COOH . ... Myristic acid, also called Tetradecanoic acid, is a common saturated fatty acid found in dairy products. ... Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated fatty acids found in animals and plants. ... A spacefilling model of the Stearic Acid molecule A diagram of the Stearic Acid molecule Stearic acid (IUPAC systematic name: octadecanoic acid) is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. ... Arachidic acid also called eicosanoic acid is a saturated fatty acid found in peanut oil. ... Behenic acid, also docosanoic acid, is a normal carboxylic acid, a fatty acid with formula C21H43COOH. In appearance, it consists of white to cream color crystals or powder with a melting point of 74-78°C and boiling point of 306°C. At 9%, it is a major component of... Lignoceric acid, also tetracosanoic acid, is a saturated fatty acid with formula C23H47COOH. Lignoceric acid is a byproduct of lignin production. ... For an explanation of n and numerical nomenclature (such as n−3 or 18:3), see Nomenclature of fatty acids. ... Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. ... Stearidonic acid is an ω-3 essential fatty acid, sometimes called moroctic acid. ... Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an omega-3 fatty acid. ... Docosahexaenoic acid (commonly known as DHA; 22:6(ω-3), all-cis-docosa-4,7,10,13,16,19-hexaenoic acid; trivial name cervonic acid) is an omega-3 essential fatty acid. ... Omega-6 fatty acids are fatty acids where the term omega-6 signifies that the first double bond in the carbon backbone of the fatty acid, counting from the end opposite the acid group, occurs in the sixth carbon-carbon bond. ... Linoleic acid (LA) is an unsaturated omega-6 fatty acid. ... gamma-Linolenic acid (GLA) is an omega-6 essential fatty acid found primarily in vegetable oils. ... Dihomo-gamma-linolenic acid (DGLA) is a 20-carbon ω-6 fatty acid. ... Arachidonic acid (AA) is an omega-6 fatty acid 20:4(ω-6). ... Omega-9 fatty acids are a class of unsaturated fatty acids which have a C=C double bond in the ω-9 position. ... Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable sources. ... Erucic acid Erucic acid is a fatty acid found in rapeseed, wallflower seed, and mustard seed, making up 40 to 50 percent of their oil. ...

  Results from FactBites:
 
Fatty acid - Wikipedia, the free encyclopedia (1676 words)
Long carboxy acids as short as butyric acid (4 carbons) are considered to be fatty acids, while fatty acids derived from natural fats and oils may be assumed to have at least 8 carbon atoms, e.g.
Industrially, fatty acids are produced by the hydrolysis of the ester linkages in a fat or biological oil (both of which are triglycerides), with the removal of glycerol.
Linoleic acid and arachidonic acid are omega-6 fatty acids.
Essential fatty acid - Wikipedia, the free encyclopedia (874 words)
Fatty acids are straight chain hydrocarbons possessing a carboxyl (COOH) group at one end (α) and (usually) a methyl group at the other (ω) end.
Some of the food sources of ω-3 and ω-6 fatty acids are fish and shellfish, flaxseed (linseed), soya oil, canola (rapeseed) oil, hemp oil, chia seeds, pumpkin seeds, sunflower seeds, leafy vegetables, and walnuts.
Essential fatty acids play a part in many metabolic processes, and there is evidence to suggest that low levels of essential fatty acids, or the wrong balance of types among the essential fatty acids, may be a factor in a number of illnesses.
  More results at FactBites »

 
 

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