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Triglyceride

A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from tri- and glyceride).[1] Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat.[2] They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.[3]

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

Many types of triglycerides exist. One specific classification focuses on saturated and unsaturated types. Saturated fats have no C=C groups; unsaturated fats feature one or more C=C groups. Unsaturated fats tend to have a lower melting point than saturated analogues; as a result, they are often liquid at room temperature.

Chemical structure edit

 
Example of a natural mixed triglyceride with residues of three different fatty acids. The first fatty acid residue is saturated (blue highlighted), the second fatty acid residue contains one double bond within the carbon chain (green highlighted). The third fatty acid residue (a polyunsaturated fatty acid residue, highlighted in red) contains three double bonds within the carbon chain. All carbon-carbon double bonds shown are cis isomers.

The three fatty acids substituents can be the same, but they are usually different. Many triglycerides are known because many fatty acids are known and their combinations are even more numerous. The chain lengths of the fatty acids in naturally occurring triglycerides vary, but most contain 16, 18, or 20 carbon atoms, defined as long-chain triglycerides, while medium-chain triglycerides contain shorter fatty acids. Animals synthesize even-numbered fatty acids, but bacteria possess the ability to synthesise odd- and branched-chain fatty acids. As a result, ruminant animal fat contains odd-numbered fatty acids, such as 15, due to the action of bacteria in the rumen. Many fatty acids are unsaturated; some are polyunsaturated (e.g., those derived from linoleic acid).[4]

Most natural fats contain a complex mixture of individual triglycerides. Because of their heterogeneity, they melt over a broad range of temperatures. Cocoa butter is unusual in that it is composed of only a few triglycerides, derived from palmitic, oleic, and stearic acids in the 1-, 2-, and 3-positions of glycerol, respectively.[4]

The simplest triglycerides are those where the three fatty acids are identical. Their names indicate the fatty acid: stearin derived from stearic acid, triolein derived from oleic acid, palmitin derived from palmitic acid, etc. These compounds can be obtained in three crystalline forms (polymorphs): α, β, and β′, the three forms differing in their melting points.[4][5]

A triglyceride containing different fatty acids is known as a mixed triglyceride.[6] If the first and third fatty acids on the glycerol differ, then the mixed triglyceride is chiral.[7]

Biosynthesis edit

Triglycerides are tri-esters derived from the condensation reaction of glycerol with three fatty acids. Their formation can be summarised by the following overall equation:

CH(OH)(CH2OH)2 + RCOOH + R'COOH + R"COOH → RC(O)OCH2−CH(OC(O)R')−CH2C(O)OR" + 3H2O

In nature, the formation of triglycerides is not random; rather, specific fatty acids are selectively condensed with the hydroxyl functional groups of glycerol. Animal fats typically have unsaturated fatty acid residues on carbon atoms 1 and 3. Extreme examples of non-random fats are cocoa butter (mentioned above) and lard, which contains about 20% triglyceride with palmitic acid on carbon 2 and oleic acid on carbons 1 and 3.[4] An early step in the biosynthesis is the formation of the glycerol-1-phosphate:[4]

CH(OH)(CH2OH)2 + H2PO4 → HOCH2−CH(OH)−CH2−OPO3H + H2O

The three oxygen atoms in this phosphate ester are differentiated, setting the stage for regiospecific formation of triglycerides, as the diol reacts selectively with coenzyme-A derivatives of the fatty acids, RC(O)S–CoA:

HOCH2−CH(OH)−CH2−OPO3H + RC(O)S−CoA + R'C(O)S−CoA → RC(O)O−CH2−CH(−OC(O)R')−CH2−OPO3H + 2HS−CoA

The phosphate ester linkage is then hydrolysed to make way for the introduction of a third fatty acid ester:

RC(O)O−CH2−CH(−OC(O)R')−CH2−OPO3H + H2O → RC(O)O−CH2−CH(−OC(O)R')−CH2OH + H2PO4
RC(O)O−CH2−CH(−OC(O)R')−CH2OH + R"C(O)S−CoA → RC(O)O−CH2−CH(−OC(O)R')−CH2−OC(O)R" + HS−CoA

Nomenclature edit

Common fat names edit

Fats are usually named after their source (like olive oil, cod liver oil, shea butter, 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 edit

Triglycerides are then commonly named as esters of those acids, as in glyceryl 1,2-dioleate 3-palmitate, the name for a brood pheromone of the honey bee.[8] Where the fatty acid residues in a triglyceride are all the same, names like olein (for glyceryl trioleate) and palmitin (for glyceryl tripalmitate) are common.

IUPAC edit

In the International Union of Pure and Applied Chemistry's (IUPAC's) general chemical nomenclature for organic compounds,[9] any organic structure can be named by starting from its corresponding hydrocarbon and then specifying differences so as to describe its structure completely. For fatty acids, for example, the position and orientation of carbon-carbon double bonds is specified counting from the carboxyl functional group. Thus, oleic acid is formally named (9Z)-octadec-9-enoic acid, which describes that the compound has:

  • an 18 carbon chain ("octadec-") with the carbon of the carboxyl ("-oic acid") given the number 1
  • all carbon-carbon bonds are single except for the double bond then joins carbon 9 ("9-en") to carbon 10
  • the chain connects to each of the carbons of the double bond on the same side (hence, cis, or "(9Z)" - the "Z" being an abbreviation for the German word zusammen, meaning together).

IUPAC nomenclature can also handle branched chains and derivatives where hydrogen atoms are replaced by other chemical groups. Triglycerides take formal IUPAC names according to the rule governing naming of esters. For example, the formal name propane-1,2,3-tryl 1,2-bis((9Z)-octadec-9-enoate) 3-(hexadecanoate) applies to the pheromone informally named as glyceryl 1,2-dioleate-3-palmitate,[8] and also known by other common names including 1,2-dioleoyl-3-palmitoylglycerol, glycerol dioleate palmitate, and 3-palmito-1,2-diolein.

Fatty acid code edit

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 positions of the trans bonds. Either or both cis and trans lists and their labels are omitted if there are no multiple bonds with that geometry. For example, the codes for stearic, oleic, elaidic, and vaccenic acids are "18:0", "18:1 cis-9", "18:1 trans-9", and "18:1 trans-11", respectively. Catalpic acid, (9E,11E,13Z)-octadeca-9,11,13-trienoic acid according to IUPAC nomenclature, has the code "18:3 cis-13 trans-9,11".

Saturated and unsaturated fats edit

For human nutrition, an important classification of fats is based on the number and position of double bonds in the constituent fatty acids. Saturated fat has a predominance of saturated fatty acids, without any double bonds, while unsaturated fat has predominantly 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.)[10][11]

Unsaturated fatty acids are further classified into monounsaturated (MUFAs), with a single double bond, and polyunsaturated (PUFAs), with two or more.[10][11] Natural fats usually contain several different saturated and unsaturated acids, even on the same molecule. For example, in most vegetable oils, the saturated palmitic (C16:0) and stearic (C18:0) 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 (C18:1, ω–9) or linoleic (C18:2, ω–6).[12])

 
Stearic acid (saturated, C18:0)
 
Palmitoleic acid (mono-unsaturated, C16:1 cis-9, omega-7)
 
Oleic acid (mono-unsaturated, C18:1 cis-9, omega-9)
 
α-Linolenic acid (polyunsaturated, C18:3 cis-9,12,15, omega-3)
 
γ-Linolenic acid (polyunsaturated, C18:3 cis-6,9,12, omega-6)

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 (flax seed), tung, poppyseed, perilla, and walnut oil, which polymerize on exposure to oxygen to form solid films, and are used to make paints and varnishes.

Saturated fats generally have a higher melting point than unsaturated 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 oils into solid or semisolid vegetable fats 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.[13]

In cellular metabolism, unsaturated fat molecules yield slightly less energy (i.e., fewer calories) than an equivalent amount of saturated fat. The heats of combustion of saturated, mono-, di-, and tri-unsaturated 18-carbon fatty acid esters have been measured as 2859, 2828, 2794, and 2750 kcal/mol, respectively; 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.[14]

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 (rancidity). Antioxidants can protect unsaturated fat from lipid peroxidation.

Industrial uses edit

Linseed oil and related oils are important components of useful products used in oil paints and related coatings. Linseed oil is rich in di- and tri-unsaturated fatty acid components, which tend to harden in the presence of oxygen. This heat-producing hardening process is peculiar to these so-called drying oils. It is caused by a polymerization process that begins with oxygen molecules attacking the carbon backbone.

Triglycerides are also split into their components via transesterification during the manufacture of biodiesel. The resulting fatty acid esters can be used as fuel in diesel engines. The glycerin has many uses, such as in the manufacture of food and in the production of pharmaceuticals.

Staining edit

Staining for fatty acids, triglycerides, lipoproteins, and other lipids is done through the use of lysochromes (fat-soluble dyes). These dyes can allow the qualification of a certain fat of interest by staining the material a specific color. Some examples: Sudan IV, Oil Red O, and Sudan Black B.

Interactive pathway map edit

Click on genes, proteins and metabolites below to link to respective articles. [§ 1]

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Statin Pathway edit
  1. ^ The interactive pathway map can be edited at WikiPathways: "Statin_Pathway_WP430".

See also edit

References edit

  1. ^ "Nomenclature of Lipids". IUPAC-IUB Commission on Biochemical Nomenclature (CBN). Retrieved 2007-03-08.
  2. ^ Nelson, D. L.; Cox, M. M. (2000). Lehninger, Principles of Biochemistry (3rd ed.). New York: Worth Publishing. ISBN 1-57259-153-6.
  3. ^ Lampe, M. A.; Burlingame, A. L.; Whitney, J.; Williams, M. L.; Brown, B. E.; Roitman, E.; Elias, M. (1983). "Human stratum corneum lipids: characterization and regional variations". J. Lipid Res. 24 (2): 120–130. doi:10.1016/S0022-2275(20)38005-6. PMID 6833889.
  4. ^ a b c d e Alfred Thomas (2002). "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_173. ISBN 3527306730.
  5. ^ Charbonnet, G. H.; Singleton, W. S. (1947). "Thermal properties of fats and oils". J. Am. Oil Chem. Soc. 24 (5): 140. doi:10.1007/BF02643296. S2CID 101805872.
  6. ^ "Mixed triglyceride | chemical compound | Britannica". www.britannica.com. Retrieved 2023-02-13.
  7. ^ Lok, C.M.; Ward, J.P.; van Dorp, D.A. (1976). "The synthesis of Chiral Glycerides starting from D- and L-serine". Chemistry and Physics of Lipids. 16 (2): 115–122. doi:10.1016/0009-3084(76)90003-7. PMID 1269065.
  8. ^ a b N. Koeniger and H. J. Veith (1983): "Glyceryl-1,2-dioleate-3-palmitate, a brood pheromone of the honey bee (Apis mellifera L.)". Experientia, volume 39, pages 1051–1052 doi:10.1007/BF01989801
  9. ^ Henri A. Favre; Warren H. Powell; et al. (International Union of Pure and Applied Chemistry) (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names, 2013 (PDF). Cambridge, England: Royal Society of Chemistry. ISBN 978-1-84973-306-9. OCLC 865143943.
  10. ^ a b "Essential Fatty Acids". Micronutrient Information Center, Oregon State University, Corvallis, OR. May 2014. Retrieved 24 May 2017.
  11. ^ a b "Omega-3 fatty acids, fish oil, alpha-linolenic acid". Mayo Clinic. 2017. Retrieved 24 May 2017.
  12. ^ Institute of Shortenings and Edible oils (2006). (PDF). Archived from the original (PDF) on 2007-03-26. Retrieved 2009-02-19.
  13. ^ Marchand, V (2010). "Trans fats: What physicians should know". Canadian Paediatric Society. 6 (15): 373–375. doi:10.1093/pch/15.6.373. PMC 2921725. PMID 21731420.
  14. ^ Krisnangkura, Kanit (1991). "Estimation of heat of combustion of triglycerides and fatty acid methyl esters". Journal of the American Oil Chemists' Society. 68: 56–58. doi:10.1007/BF02660311. S2CID 84433984.

External links edit

  • Lowering Triglycerides (EMedicineHealth.com; October 2020)

triglyceride, triglyceride, triacylglycerol, triacylglyceride, ester, derived, from, glycerol, three, fatty, acids, from, glyceride, main, constituents, body, humans, other, vertebrates, well, vegetable, they, also, present, blood, enable, bidirectional, trans. A triglyceride TG triacylglycerol TAG or triacylglyceride is an ester derived from glycerol and three fatty acids from tri and glyceride 1 Triglycerides are the main constituents of body fat in humans and other vertebrates as well as vegetable fat 2 They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver and are a major component of human skin oils 3 Example of an unsaturated fat triglyceride C55H98O6 Left part glycerol right part from top to bottom palmitic acid oleic acid alpha linolenic acid Many types of triglycerides exist One specific classification focuses on saturated and unsaturated types Saturated fats have no C C groups unsaturated fats feature one or more C C groups Unsaturated fats tend to have a lower melting point than saturated analogues as a result they are often liquid at room temperature Contents 1 Chemical structure 2 Biosynthesis 3 Nomenclature 3 1 Common fat names 3 2 Chemical fatty acid names 3 3 IUPAC 3 4 Fatty acid code 4 Saturated and unsaturated fats 5 Industrial uses 6 Staining 7 Interactive pathway map 8 See also 9 References 10 External linksChemical structure edit nbsp Example of a natural mixed triglyceride with residues of three different fatty acids The first fatty acid residue is saturated blue highlighted the second fatty acid residue contains one double bond within the carbon chain green highlighted The third fatty acid residue a polyunsaturated fatty acid residue highlighted in red contains three double bonds within the carbon chain All carbon carbon double bonds shown are cis isomers The three fatty acids substituents can be the same but they are usually different Many triglycerides are known because many fatty acids are known and their combinations are even more numerous The chain lengths of the fatty acids in naturally occurring triglycerides vary but most contain 16 18 or 20 carbon atoms defined as long chain triglycerides while medium chain triglycerides contain shorter fatty acids Animals synthesize even numbered fatty acids but bacteria possess the ability to synthesise odd and branched chain fatty acids As a result ruminant animal fat contains odd numbered fatty acids such as 15 due to the action of bacteria in the rumen Many fatty acids are unsaturated some are polyunsaturated e g those derived from linoleic acid 4 Most natural fats contain a complex mixture of individual triglycerides Because of their heterogeneity they melt over a broad range of temperatures Cocoa butter is unusual in that it is composed of only a few triglycerides derived from palmitic oleic and stearic acids in the 1 2 and 3 positions of glycerol respectively 4 The simplest triglycerides are those where the three fatty acids are identical Their names indicate the fatty acid stearin derived from stearic acid triolein derived from oleic acid palmitin derived from palmitic acid etc These compounds can be obtained in three crystalline forms polymorphs a b and b the three forms differing in their melting points 4 5 A triglyceride containing different fatty acids is known as a mixed triglyceride 6 If the first and third fatty acids on the glycerol differ then the mixed triglyceride is chiral 7 Biosynthesis editTriglycerides are tri esters derived from the condensation reaction of glycerol with three fatty acids Their formation can be summarised by the following overall equation CH OH CH2OH 2 RCOOH R COOH R COOH RC O OCH2 CH OC O R CH2C O OR 3H2OIn nature the formation of triglycerides is not random rather specific fatty acids are selectively condensed with the hydroxyl functional groups of glycerol Animal fats typically have unsaturated fatty acid residues on carbon atoms 1 and 3 Extreme examples of non random fats are cocoa butter mentioned above and lard which contains about 20 triglyceride with palmitic acid on carbon 2 and oleic acid on carbons 1 and 3 4 An early step in the biosynthesis is the formation of the glycerol 1 phosphate 4 CH OH CH2OH 2 H2PO 4 HOCH2 CH OH CH2 OPO3H H2OThe three oxygen atoms in this phosphate ester are differentiated setting the stage for regiospecific formation of triglycerides as the diol reacts selectively with coenzyme A derivatives of the fatty acids RC O S CoA HOCH2 CH OH CH2 OPO3H RC O S CoA R C O S CoA RC O O CH2 CH OC O R CH2 OPO3H 2HS CoAThe phosphate ester linkage is then hydrolysed to make way for the introduction of a third fatty acid ester RC O O CH2 CH OC O R CH2 OPO3H H2O RC O O CH2 CH OC O R CH2OH H2PO 4RC O O CH2 CH OC O R CH2OH R C O S CoA RC O O CH2 CH OC O R CH2 OC O R HS CoANomenclature editCommon fat names edit Fats are usually named after their source like olive oil cod liver oil shea butter 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 edit Triglycerides are then commonly named as esters of those acids as in glyceryl 1 2 dioleate 3 palmitate the name for a brood pheromone of the honey bee 8 Where the fatty acid residues in a triglyceride are all the same names like olein for glyceryl trioleate and palmitin for glyceryl tripalmitate are common IUPAC edit In the International Union of Pure and Applied Chemistry s IUPAC s general chemical nomenclature for organic compounds 9 any organic structure can be named by starting from its corresponding hydrocarbon and then specifying differences so as to describe its structure completely For fatty acids for example the position and orientation of carbon carbon double bonds is specified counting from the carboxyl functional group Thus oleic acid is formally named 9Z octadec 9 enoic acid which describes that the compound has an 18 carbon chain octadec with the carbon of the carboxyl oic acid given the number 1 all carbon carbon bonds are single except for the double bond then joins carbon 9 9 en to carbon 10 the chain connects to each of the carbons of the double bond on the same side hence cis or 9Z the Z being an abbreviation for the German word zusammen meaning together IUPAC nomenclature can also handle branched chains and derivatives where hydrogen atoms are replaced by other chemical groups Triglycerides take formal IUPAC names according to the rule governing naming of esters For example the formal name propane 1 2 3 tryl 1 2 bis 9Z octadec 9 enoate 3 hexadecanoate applies to the pheromone informally named as glyceryl 1 2 dioleate 3 palmitate 8 and also known by other common names including 1 2 dioleoyl 3 palmitoylglycerol glycerol dioleate palmitate and 3 palmito 1 2 diolein Fatty acid code edit 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 positions of the trans bonds Either or both cis and trans lists and their labels are omitted if there are no multiple bonds with that geometry For example the codes for stearic oleic elaidic and vaccenic acids are 18 0 18 1 cis 9 18 1 trans 9 and 18 1 trans 11 respectively Catalpic acid 9E 11E 13Z octadeca 9 11 13 trienoic acid according to IUPAC nomenclature has the code 18 3 cis 13 trans 9 11 Saturated and unsaturated fats editFor human nutrition an important classification of fats is based on the number and position of double bonds in the constituent fatty acids Saturated fat has a predominance of saturated fatty acids without any double bonds while unsaturated fat has predominantly 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 10 11 Unsaturated fatty acids are further classified into monounsaturated MUFAs with a single double bond and polyunsaturated PUFAs with two or more 10 11 Natural fats usually contain several different saturated and unsaturated acids even on the same molecule For example in most vegetable oils the saturated palmitic C16 0 and stearic C18 0 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 C18 1 w 9 or linoleic C18 2 w 6 12 nbsp Stearic acid saturated C18 0 nbsp Palmitoleic acid mono unsaturated C16 1 cis 9 omega 7 nbsp Oleic acid mono unsaturated C18 1 cis 9 omega 9 nbsp a Linolenic acid polyunsaturated C18 3 cis 9 12 15 omega 3 nbsp g Linolenic acid polyunsaturated C18 3 cis 6 9 12 omega 6 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 flax seed tung poppyseed perilla and walnut oil which polymerize on exposure to oxygen to form solid films and are used to make paints and varnishes Saturated fats generally have a higher melting point than unsaturated 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 oils into solid or semisolid vegetable fats 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 13 In cellular metabolism unsaturated fat molecules yield slightly less energy i e fewer calories than an equivalent amount of saturated fat The heats of combustion of saturated mono di and tri unsaturated 18 carbon fatty acid esters have been measured as 2859 2828 2794 and 2750 kcal mol respectively 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 14 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 rancidity Antioxidants can protect unsaturated fat from lipid peroxidation Industrial uses editLinseed oil and related oils are important components of useful products used in oil paints and related coatings Linseed oil is rich in di and tri unsaturated fatty acid components which tend to harden in the presence of oxygen This heat producing hardening process is peculiar to these so called drying oils It is caused by a polymerization process that begins with oxygen molecules attacking the carbon backbone Triglycerides are also split into their components via transesterification during the manufacture of biodiesel The resulting fatty acid esters can be used as fuel in diesel engines The glycerin has many uses such as in the manufacture of food and in the production of pharmaceuticals Staining editStaining for fatty acids triglycerides lipoproteins and other lipids is done through the use of lysochromes fat soluble dyes These dyes can allow the qualification of a certain fat of interest by staining the material a specific color Some examples Sudan IV Oil Red O and Sudan Black B Interactive pathway map editClick on genes proteins and metabolites below to link to respective articles 1 File nbsp nbsp alt Statin Pathway edit Statin Pathway edit The interactive pathway map can be edited at WikiPathways Statin Pathway WP430 See also editDiglyceride acyltransferase an enzyme that produces triglycerides Glycerol 3 phosphate acyltransferases enzymes involved in early step in biosynthesis of triglycerides Phosphatidic acids playing a role in biosynthesis of triglycerides Medium chain triglycerides Lipid profile Lipids Vertical auto profile Hypertriglyceridemia the presence of high amounts of triglycerides in the blood References edit Nomenclature of Lipids IUPAC IUB Commission on Biochemical Nomenclature CBN Retrieved 2007 03 08 Nelson D L Cox M M 2000 Lehninger Principles of Biochemistry 3rd ed New York Worth Publishing ISBN 1 57259 153 6 Lampe M A Burlingame A L Whitney J Williams M L Brown B E Roitman E Elias M 1983 Human stratum corneum lipids characterization and regional variations J Lipid Res 24 2 120 130 doi 10 1016 S0022 2275 20 38005 6 PMID 6833889 a b c d e Alfred Thomas 2002 Fats and Fatty Oils Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a10 173 ISBN 3527306730 Charbonnet G H Singleton W S 1947 Thermal properties of fats and oils J Am Oil Chem Soc 24 5 140 doi 10 1007 BF02643296 S2CID 101805872 Mixed triglyceride chemical compound Britannica www britannica com Retrieved 2023 02 13 Lok C M Ward J P van Dorp D A 1976 The synthesis of Chiral Glycerides starting from D and L serine Chemistry and Physics of Lipids 16 2 115 122 doi 10 1016 0009 3084 76 90003 7 PMID 1269065 a b N Koeniger and H J Veith 1983 Glyceryl 1 2 dioleate 3 palmitate a brood pheromone of the honey bee Apis mellifera L Experientia volume 39 pages 1051 1052 doi 10 1007 BF01989801 Henri A Favre Warren H Powell et al International Union of Pure and Applied Chemistry 2014 Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 PDF Cambridge England Royal Society of Chemistry ISBN 978 1 84973 306 9 OCLC 865143943 a b Essential Fatty Acids Micronutrient Information Center Oregon State University Corvallis OR May 2014 Retrieved 24 May 2017 a b Omega 3 fatty acids fish oil alpha linolenic acid Mayo Clinic 2017 Retrieved 24 May 2017 Institute of Shortenings and Edible oils 2006 Food Fats and oils PDF Archived from the original PDF on 2007 03 26 Retrieved 2009 02 19 Marchand V 2010 Trans fats What physicians should know Canadian Paediatric Society 6 15 373 375 doi 10 1093 pch 15 6 373 PMC 2921725 PMID 21731420 Krisnangkura Kanit 1991 Estimation of heat of combustion of triglycerides and fatty acid methyl esters Journal of the American Oil Chemists Society 68 56 58 doi 10 1007 BF02660311 S2CID 84433984 External links edit nbsp Chemistry portalLowering Triglycerides EMedicineHealth com October 2020 Retrieved from https en wikipedia org w index php title Triglyceride amp oldid 1188346485, wikipedia, wiki, book, books, library,

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